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Ashland Holiday Rentals

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    Travellers to Ashland are booking October dates now. Secure your holiday rental today, and have the perfect trip.
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    4BR Ashland Lodge Style House w/Patio!1 / 31
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    Abigail's Cottage, 10-min. walk to plaza/theaters1 / 20
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Oak Street Cottages ~ Sherwin ~ 1.5 Blocks to Oregon Shakespeare Festival!1 / 12
    (6)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    Private Suite Near Shakespeare1 / 17
    (19)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
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    Pet friendly
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    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Red Birch Ranch Luxury Apartment1 / 17
    (14)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Satellite TV
    • Terrace
    • Washer
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    • Balcony
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Private and Luxurious Cottage Constructed in 2015 with High End Amenities1 / 26
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Sauna
    • DVD Player
    • Washer
    • Mountain Views
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Perfect Ashland get away.
    Reviewed 15 March 2017
    I felt welcome in the cottage as the owners greeted me upon arrival and took the time to show me around, explained how things worked, and even offered me a chilled bottle of...
    Luxury Ashland, Oregon condo!!
    Reviewed 7 March 2017
    Great location within walking distance to cute little coffee houses and restaurants!! Love the historical neighborhood. Owners went to such detail when building this beautiful...
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    About this property
    Award winning ultra modern luxury cottage located on nearly a half acre estate 3-4 blocks from Ashland Plaza, Lithia Park and the Oregon Shakespeare Festival grounds. The cottage was built in 2015 directly behind the historic Leeke-Mills house build in 1885 and completely renovated in 2007. Ashland...
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    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Cozy & Private Studio Cottage in Garden Sanctuary + Walk to Downtown Plaza1 / 23
    (6)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    • Hot Tub
    • Parking
    • Terrace
    • Patio
    • Grill
    • Air Conditioning
    • Balcony
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    Pet friendly
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    Smoking allowed
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    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 1
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    BOOK 2 NIGHTS-GET 1 FREE! Cabin On Hyatt Lake ~ Sleeps Six ~ New Hot Tub! (#44)1 / 22
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
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    • Satellite TV
    • DVD Player
    • Hot Tub
    • Central Heating
    • Patio
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    Pet friendly
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    Smoking allowed
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Ashland Artist Country Retreat, Just 5 Minutes from Town!1 / 11
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Garden Cottage close to Downtown Ashland1 / 6
    (6)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Location Information
    Ashland, Oregon 97520 2650
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Red Birch Ranch Deluxe Coach1 / 11
    (2)Poor
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Internet Access
    • DVD Player
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    Pet friendly
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    Smoking allowed
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    The Cottage at Grizzly Peak Winery - Sleeps 41 / 9
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    Location, Location, Location
    Reviewed 4 August 2017
    What a sweet location, parklike grounds, vineyard, winery and wonderful welcoming hosts. Virginia & Al made us feel right at home. The cottage is clean, comfortable and...
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    About this property
    Enjoy a free bottle of wine... let us know, red or white... and free admission to one of our summertime concerts (if it coincides with your stay). Nestled on the slopes of Grizzly Peak, less than ten minutes from Downtown Ashland sits our second floor studio cottage! A 600sqft+ studio cottage...
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    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Pioneer House ~ One Block from OSF1 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Satellite TV
    • Private Garden
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    Pet friendly
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    Smoking allowed
    About this property
    Just 2 blocks to Downtown Ashland Plaza... and 1 block from OSF make this a perfect getaway! This two-story home has three bedrooms; the master has a king-size bed and the guest rooms each have queen-sized beds. There is a spacious living room with plenty of seating and a sofa-bed. The home can...
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    Ashland, Oregon 97520
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Ashland Summer Vacation Rental - August 20181 / 13
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Internet Access
    • Patio
    • Sauna
    • Washer
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    RedTail Inn ~ The "Red" McCall Suite ~ Sleeps Six1 / 11
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A 1900's Classic Farmhouse REBORN! Red Tail ... Downtown Ashland's Luxury Boutique Inn is NOW OPEN! Enjoy your four block walk to Oregon's Shakespeare Festival as you pass local Coffee Bars, Shops, and Restaurants ~ Furnishings mix Modern Farmhouse, Art Nouveau and feature Local Artist Kay...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Perfect vacation cottage1 / 25
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Yes, the 'perfect vacation cottage' is...PERFECT!
    Reviewed 3 July 2016
    Perfectly furnished for our party of four adults; perfectly stocked kitchen; perfect front yard for dining al fresco and watching deer go by; perfect neighborhood for daily...
    Pretty perfect!
    Reviewed 24 August 2015
    Great location for walking to theatres as well as restaurantsand shopping in Ashland. Great space for two couples tobe separate or to be together. Front porch is a...
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    About this property
    Fully restored vintage cottage in a quiet neighborhood just steps away from downtown Ashland and the theater. Surrounded by lovely gardens assuring a private and serene environment. The cottage is tastefully decorated , is immaculate and has 2 bedrooms, 2 baths, office, full kitchen, front porch...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    '1900' House ~ Downtown Ashland - Near Oregon Shakespeare Festival ~ Sleeps 81 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Patio
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Note: '1900' Guest House (Next Door) May Also Be Available: (It features a King Bed and Full Kitchen and Bathroom) The Historic '1900' House is the best of Downtown Ashland... and less than five blocks to the renowned Oregon Shakespeare Festival. A quiet residential neighborhood, our home features...
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    Ashland, Oregon 97520
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Oak Street Cottages~Tower Townhouse ~ 1.5 Blocks to Oregon Shakespeare Festival!1 / 9
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Wi-Fi
    • Terrace
    • Balcony
    • Grill
    • Air Conditioning
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    (NOTE: Listed through the City of Ashland as Oak Street Cottages) Located in the heart of Downtown Ashland, Oak Tower Townhouse is one of the closest properties to the famed Oregon Shakespeare Festival, and just one and half blocks to the entry of the Theaters. The home features a full kitchen, a...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Juliet1 / 15
    (3)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Garden
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Mountain Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Shakespeare festival stay
    Reviewed 2 July 2017
    The accommodations were well equipped. The beds were very comfortable and we enjoyed sitting on the patio in the mornings and reading or drawing.
    Charming spot
    Reviewed 23 July 2014
    I took my 86 year old mother with me to visit Ashland. The cottage was very clean and cozy and my mom was delighted. There is no real living or dining space inside but the...
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    About this property
    Newly remodeled for modern comfort, the Lori Lane Cottages are only a short walk from the Oregon Shakespeare Festival (OSF) and downtown Ashland, where you can experience world class shopping and fantastic local restaurants. Guests have access to private off-street parking and fully stocked...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Oak Street Cottages ~ Oak Lawn ~ 1.5 Blocks to Oregon Shakespeare Festival!1 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    (NOTE: Listed through the City of Ashland as Oak Street Cottages) Located in the heart of Downtown Ashland, Oak Lawn Cottage is one of the closest properties to the famed Oregon Shakespeare Festival, at just one and half blocks to the entry of the Theaters. The home features a full kitchen,...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Oak Street Cottages ~ Hideaway ~ 1.5 Blocks to Oregon Shakespeare Festival!1 / 9
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    (NOTE: Listed through the City of Ashland as Oak Street Cottages) Located in the heart of Downtown Ashland, Hideaway Cottage is one of the closest properties to the famed Oregon Shakespeare Festival, at just one and half blocks to the entry of the Theaters. The home features a full kitchen,...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Whispering Pines Cabin at Hyatt Lake ~ 3RD NIGHT FREE ~ Sleeps 81 / 31
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3RD NIGHT FREE PROMOTION: SEPTEMBER 15th to APRIL 30th *Blackout Dates: Thanksgiving Week and Christmas Week through New Years Hyatt Lake Cabin Home! 1.5 acres and close access to the lake. Just 5 minutes from the Hyatt Lake Resort, the Pacific Crest Trail and the Table Mountain Winter Play Area!...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Romeo1 / 12
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Garden
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Patio
    • Satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Outstanding, beautiful, and relaxing!
    Reviewed 8 August 2015
    We have been staying at this property once a year for over 10 years, and we can hardly wait to return the next year. This rental and it's adjacent cottage are beautifully...
    An excellent site, well located, with genial hosts.
    Reviewed 23 July 2015
    We stayed three days at Lori Lane. There were four of us and it suited us very well. It is walking distance to downtown and the OSF. We ate our breakfasts and a couple of...
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    About this property
    Newly remodeled for modern comfort, the Lori Lane Cottages are only a short walk from the Oregon Shakespeare Festival (OSF) and downtown Ashland, where you can experience world class shopping and fantastic local restaurants. Guests have access to private off-street parking and fully stocked...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Meadow House on a Historic Ranch in Ashland, OR1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Porch
    • Grill
    • Wi-Fi
    • Mountain Views
    • Hot Tub
    • Washer
    • Parking
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Meadow House, built in 2000, features natural wood and plaster throughout, a well-stocked cook's kitchen with fresh eggs and milk in the refrigerator, and the quiet of off-grid living. The three bedroom, two bath house sleeps up to ten comfortably with 3 twin beds in the West Bedroom, a queen bed...
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    Ashland, Oregon 97520
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    RedTail Inn ~ The Orliena McCall Suite ~ Sleeps Four1 / 8
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A 1900's Classic Farmhouse REBORN! Red Tail ... Downtown Ashland's Luxury Boutique Inn (scheduled for completion in Spring 2017) Enjoy your four block walk to Oregon's Shakespeare Festival as you pass local Coffee Bars, Shops, and Restaurants ~ Furnishings mix Modern Farmhouse, Art Nouveau and...
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    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    The Stone Villa ~ In the Hills of Ashland (Sleeps 4)1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Central Heating
    • Parking
    • Mountain Views
    • Patio
    • Balcony
    • Wi-Fi
    • Washer
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tastefully nestled into the hills of Ashland, in a quiet country setting, 2 miles from downtown. The stone villa is an uniquely designed solar home, with abundant entertaining space both inside and out. There are two large, lovely view bedrooms, one upstairs, one downstairs. Each has a private...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Hopyard Views Farm - Minutes to Downtown Ashland!1 / 21
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Central Heating
    • Parking
    • Mountain Views
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Quiet, rural, 5 minutes to downtown Ashland
    Reviewed 3 weeks ago
    We loved getting a glimpse of the hop harvest in progress just outside our door. Also, the couple that greeted us and lived in attached quarters was friendly and helped us...
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    About this property
    Just a quick five minutes from Downtown Ashland! Views of mountains, sheep, and chickens can be enjoyed from YOUR private deck, with (seasonal) hops, grapes and blackberries growing right outside your bedroom window This spacious modern suite is bright and comfortable, has a private entrance,...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The Terra Cottage Inn a beautiful Luxury Apartment1 / 10
    (10)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Mountain Views
    • Satellite TV
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    An amazing experience
    Reviewed 28 August 2013
    Terra Cotta Cottage is a beautiful place to stay in Ashland. Every need has been anticipated with artistic thoughtfulness.Staying there was an experience in itself. From the koi...
    Fantastic place with great hosts!
    Reviewed 12 April 2013
    We thoroughly enjoyed our stay in Terra Cottage Inn. The space was perfect for our family of four with two young children. The beds were comfy for everyone. The whole...
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    About this property
    Nestled into one of Ashland's best neighborhoods, the Terra Cottage Inn is a clean and beautiful, hand-crafted artists' cottage. Full of art, hand thrown pottery, custom built furniture and all the amenities to make this a true luxury experience. Quality comfortable beds with high thread count...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The High Street Cottage An Artists' Garden Cottage1 / 10
    (6)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Porch
    • Satellite TV
    • Patio
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Perfect space within walking distance of everything
    Reviewed 4 March 2016
    My boyfriend and I did "experience" gifts for each other at Christmas and this was mine to him. We loved it! Fantastic craftsman cottage with all the amenities you need...
    Charming, Quiet and Close to Everything
    Reviewed 10 July 2014
    The High Street Cottage is our new favorite place to stay in Ashland. The cottage and grounds were beautifully maintained and thoughtfully stocked with coffee, tea, cooking...
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    About this property
    Set in Ashland's best neighborhood, this 1931 cottage has been lovingly restored and set up to address your every need. Cozy and incredibly clean, filled with art, hand-made pottery, antiques and hand crafted furniture. Comfortable beds, high quality linens and a fully equipped kitchen. A truly...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Singing Birds Cabin1 / 15
    (23)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Parking
    • Grill
    • Porch
    • Central Heating
    • Wi-Fi
    • Outdoor Dining Area
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Just beautiful location to reconnect with nature.
    Reviewed 29 July 2017
    My husband and I had the best vacation at this cozy log cabin.The location was perfect.The view from the porch was just wonderful.Every morning of our week there we enjoyed our...
    secluded cabin in a mountain meadow
    Reviewed 25 July 2016
    We had a great time at the Singing Birds. The weather was perfect, which helped, and we enjoyed the seclusion of the location along with the comfort of the rustic cabin. Kind...
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    About this property
    Beautiful log cabin in the Southern Oregon Cascade Mountains. Located very privately on 160 acres of mountain meadowland. Cabin sleeps up to 6 people, but the only door is on the downstairs bath with sleeping beds in the open loft and also downstairs. Full kitchen, full bath down and half bath...
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    Location Information
    Ashland, Oregon 97520
    Cabin Holiday Rental - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Country Cottage Apartment1 / 23
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Patio
    • Porch
    • Wi-Fi
    • Outdoor Dining Area
    • Mountain Views
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    The perfect place just outside of Ashland!
    Reviewed 4 weeks ago
    This lovely cottage is absolutely perfect! It is clean, airy, and tastefully decorated. As you enter the cottage into the living room, you already feel how beautiful...
    Beautiful setting, comfortable stay
    Reviewed 9 May 2016
    This cozy cottage in a ranch setting was also a nice getaway from town. Organic eggs, local bread, butter and jam supplied by our host made us feel welcome and provided...
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    About this property
    Private cottage apartment with full kitchen and living area adjacent to family home. Covered porch and garden area to enjoy. Less than 15 minutes to Shakespeare Festival and downtown Ashland. Fresh eggs, local bread, jam, 1/2 and 1/2, milk and butter are stocked in fridge. There is also Nespresso,...
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    Location Information
    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Bel Canto ~ Ashland Hillside ~ Five Minutes from OSF1 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    High above the hamlet of Ashland sits Bel Canto, your bungalow with views of the surrounding city and the east mountainside. The property features two private bedrooms, with a queen and full. The large living and dining area feature a sectional sofa and flat panel television. There is also a...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    (#51) Hyatt Lake Cabin ~ 3RD NIGHT FREE ~ Sleeps 61 / 10
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Central Heating
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    • Hot Tub
    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
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    3RD NIGHT FREE PROMOTION: SEPTEMBER 15th to APRIL 30th *Blackout Dates: Thanksgiving Week and Christmas Week through New Years Where the Southwest meets the Northwest... Views of Hyatt Lake, the Steel Trestle Bridge, the surrounding Alpine Forest... and just eighteen miles from downtown Ashland!...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Farmhouse Studio at Willow Witt Ranch1 / 6
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Mountain Views
    • Porch
    • Outdoor Dining Area
    • Shared Garden
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    Pet friendly
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    About this property
    STAY <BR>Overlooking beautiful meadows, the light filled studio sleeps up to six with two queen beds in the loft rooms and a double sofa-bed downstairs. The Farrmhouse Studio also features a wood stove and a full kitchen stocked with dry goods. On-Farm Store has all our meats, sausages, eggs and...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Affordable Private Retreat with Spectacular Views1 / 17
    (8)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • Internet Access
    • Mountain Views
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    • Porch
    • Balcony
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    Suitability
    Pet friendly
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    Smoking allowed
    Designed for Maximum Comfort with Fabulous Views!
    Reviewed 21 April 2015
    Our hosts, Marty and Michael, have created a wonderfully comfortable and beautiful place to stay. The Treehouse Retreat is just outside the town of Ashland, located next to a...
    The perfect, romantic getaway
    Reviewed 4 January 2014
    The 'treehouse' was a charming and lovely vacation rental. Everything from a well-functioning, well stocked kitchen with a beautiful view, to the large, private deck and...
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    About this property
    Just minutes from the Shakespeare Festival, yet secluded in the hills above Ashland, this second floor apartment has incredible views and all the comforts of home, You will especially enjoy stepping onto your completely private, 300 sf deck which overlooks a seasonal creek and the forest with...
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    Location Information
    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2nd Street Cottages, HERITAGE HOUSE1 / 16
    (5)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • Balcony
    • Private Garden
    • Air Conditioning
    • DVD Player
    • Terrace
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Perfection
    Reviewed 15 April 2017
    I would go back to Ashland just to stay here. Seriously. We were passing through on our way to California and needed somewhere tho spend the night. What a lucky accident! The...
    Perfect Vacation
    Reviewed 12 November 2016
    Just enjoyed 5 nights at the 2nd Street Cottages. Everything was perfect. We flew in from the east coast and got in close to midnight but Sugar was there to greet us. She...
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    About this property
    THE HERITAGE SUITE IS A DELIGHTFUL 4 BEDROOM, 3 FULL BATH COTTAGE THAT ACCOMMODATES 8 GUESTS COMFORTABLY. Second Street Cottages is located on a quiet side street in the historic and beautiful Railroad District. Built in 1900, this home has been lovingly restored with great attention to detail...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Beautiful Farmhouse on Working Horse Ranch1 / 16
    (1)Poor
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    About this property
    Wonderful Craftsman-style FARMHOUSE built in 1912 and BUNKHOUSE on a working horse ranch just 3 minutes from downtown Ashland, home of the renowned Shakespeare festival and Britt festivals in nearby historic Jacksonville.<BR><BR>'FARMHOUSE' has 4 bedrooms and 2 full baths. All rooms have queen beds...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    RedTail Inn ~ The Louisa McCall Suite ~ Sleeps Two1 / 6
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    A 1900's Classic Farmhouse REBORN! Red Tail ... Downtown Ashland's Luxury Boutique Inn (scheduled for completion in Spring 2017) Enjoy your four block walk to Oregon's Shakespeare Festival as you pass local Coffee Bars, Shops, and Restaurants ~ Furnishings mix Modern Farmhouse, Art Nouveau and...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    (#33) Cabin at Hyatt Lake - 3RD NIGHT FREE - Sleeps 61 / 9
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
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    • Waterfront
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    Kid friendly
    Smoking allowed
    About this property
    3RD NIGHT FREE PROMOTION: SEPTEMBER 15th to APRIL 30th *Blackout Dates: Thanksgiving Week and Christmas Week through New Years Just eighteen miles east of Ashland and the LARGEST CABIN AT HYATT LAKE! Just a three minute walk to Hyatt Lake, with a covered Hot tub, and a huge deck overlooking...
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    Ashland, Oregon 97520
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    (#34) Cabin at Hyatt Lake - 3RD NIGHT FREE - Sleeps 51 / 12
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Grill
    • Hot Tub
    • Mountain Views
    • Wi-Fi
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    • DVD Player
    • Central Heating
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3RD NIGHT FREE PROMOTION: SEPTEMBER 15th to APRIL 30th *Blackout Dates: Thanksgiving Week and Christmas Week through New Years Just eighteen miles east of Ashland and POCKET VIEWS OF HYATT LAKE! Welcome to your Hyatt Lake Cabin, with a BBQ, and a large deck overlooking the forest, and pocket views...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    (#32) Cabin at Hyatt Lake - 3RD NIGHT FREE - Sleeps 61 / 9
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Central Heating
    • DVD Player
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    • Waterfront
    • Hot Tub
    • Grill
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3RD NIGHT FREE PROMOTION: SEPTEMBER 15th to APRIL 30th *Blackout Dates: Thanksgiving Week and Christmas Week through New Years Just eighteen miles east of Ashland and POCKET VIEWS OF HYATT LAKE! Welcome to your Hyatt Lake Cabin, with a BBQ, and a large deck overlooking the forest, and pocket...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Art & Garden Cottage ~ Minutes from Downtown Ashland1 / 8
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Central Heating
    • Wi-Fi
    • Private Garden
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    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the East Ashland countryside, and exactly three miles from the famous Downtown Ashland Plaza and Oregon Shakespeare Festival, our cottage has it all! Enjoy the gardens, the mountain views, and the artwork of local Artist, Michael Gibson. Enjoy the Art and Gardens of one of Ashland's...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    (#46) Cabin at Hyatt Lake - 3RD NIGHT FREE - Sleeps 41 / 9
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Satellite TV
    • Central Heating
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Mountain Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3RD NIGHT FREE PROMOTION: SEPTEMBER 15th to APRIL 30th *Blackout Dates: Thanksgiving Week and Christmas Week through New Years Eighteen miles east of downtown Ashland and just a three minute walk to the lake... Your cabin has a hot tub and a deck overlooking the forest... with pocket views of...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    (#40) Cabin at Hyatt Lake - 3RD NIGHT FREE - Sleeps Six1 / 9
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Satellite TV
    • Mountain Views
    • Parking
    • Central Heating
    • Grill
    • Hot Tub
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3RD NIGHT FREE PROMOTION: SEPTEMBER 15th to APRIL 30th *Blackout Dates: Thanksgiving Week and Christmas Week through New Years *This Cabin has a twin next door Eighteen Miles East of Ashland and just a three minute walk to Hyatt Lake, this cabin has a hot tub and a large deck overlooking the...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Butler's Quarters ~ Downtown Ashland (Private Entry)1 / 9
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    PRIVATE ENTRY AND PARKING As long time Owners of a Bed&Breakfast, our 'Butler's Quarters' features one bedroom (queen bed) and a private bathroom (shower). The room has a flat panel television, cable tv, wireless internet, refrigerator, microwave, and Keurig coffee maker. There is a beautiful...
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    Location Information
    Ashland, Oregon 97520
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    (#44) Cabin at Hyatt Lake - 3RD NIGHT FREE - Sleeps Six1 / 11
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3RD NIGHT FREE PROMOTION: SEPTEMBER 15th to APRIL 30th *Blackout Dates: Thanksgiving Week and Christmas Week through New Years Eighteen miles east of downtown Ashland... Just a three minute walk to Hyatt Lake, your cabin has a new hot tub and a huge deck overlooking the forest... with pocket views...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    (#39) Cabin at Hyatt Lake - 3RD NIGHT FREE - Sleeps Six1 / 10
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Hot Tub
    • Wi-Fi
    • DVD Player
    • Parking
    • Central Heating
    • Mountain Views
    • Grill
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3RD NIGHT FREE PROMOTION: SEPTEMBER 15th to APRIL 30th *Blackout Dates: Thanksgiving Week and Christmas Week through New Years Eighteen Miles East of Ashland... *This Cabin has a twin next door Just a three minute walk to Hyatt Lake, this cabin has a hot tub and a large deck overlooking the...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Best Location, Impeccable Style and Ultimate Comfort1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Satellite TV
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    Smoking allowed
    About this property
    Our cottage is where you want to stay in Ashland! From its fantastic location to its custom craftsman design to the overall comfort, you'll be delighted with your choice! Just 3 level blocks from the downtown Ashland Plaza and Shakespeare festival. Along with clean, quality and location,...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In The Heart Of Ashland1 / 7
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Second Spring Property We are excited to announce that our property was given The Ashland Historic Preservation Award in 2014. This luxury vacation property is uniquely designed for elegance and comfort that will make you feel right at home. This newly renovated craftsman can be rented as a 3...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Steps to theatres, shopping, dining, nightlife...1 / 21
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
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    Pet friendly
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    Smoking allowed
    About this property
    Beautiful, historic, fully renovated home with four bedrooms, three full baths and a fabulous welcoming front porch. Can be rented with Garden Suite, a 2 bedroom, 2 full bath house that sleeps five. Perfect location for your visit to Ashland. Historic Railroad District is situated between two...
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    Location Information
    Ashland, Oregon 97520
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Ashland Holiday Rentals

    Are you looking for the perfect holiday rental in Ashland, Ore.? Then come on in and take a look. Ashland, noted for its postcard picture perfect seasons, beautiful topography and friendly people, is the perfect holiday spot. Now that you’ve found it, you need someplace to stay. Rental cabins are a wonderful option and may be ideal for you and your family. Many are only a hop, skip and a jump from Ashland amenities, while affording you the privacy you desire. Make it a holiday to remember with a rental cottage, condo or cabin. With multiple price points and rental options, you’re sure to find something that fits your budget – and we can help.

    Ashland Activities

    If you’re looking for something to do while you’re in Ashland, head on over to the Oregon Shakespeare Festival. Each season brings something different for Shakespeare lovers ranging from tours to your favorite play. Other cultural events include the Oregon Cabaret Theater and the Ashland Independent Film Festival. Ashland is also home to more than 80 art galleries and multiple museums, such as the ScienceWorks Hands On Museum for children and the Ashland Art Center. From your home away from home holiday rental, plan your day around the activities that suit you best!

    Romancing Ashland

    Of course, with its beautiful location at the base of the Cascade Mountain Range, Ashland is perfect for lovers. Let us help you find a quaint rental cottage for two, while you focus on romance! Wine and dine with the best of them at several area restaurants including Chateaulin French restaurant. Here, you’ll find the perfect ambiance in the intimate and romantic dining room as well as an extensive wine list and gourmet French food. Or try the nationally acclaimed Winchester Restaurant at the Winchester Inn. Take your chocolate loving sweetie to the Oregon Chocolate Festival or go for a bike ride on the Mt. Ashland Mountain Bike Trail.

    Ashland is for Skiing and Golf

    With several mountain ranges in the Southern Oregon area, Ashland is perfect for the ski enthusiast! Hit the slopes at any one of the area resorts with trails ranging from beginner to professional, cross country to downhill. Find a rental cabin with access just outside your door and you’ll be in ski heaven. Located at 7,500 feet, Mt. Ashland offers skiing during the season from November to April on a variety of trails for any skill level as well as snowboarding. Golf resorts include Oak Knoll in Ashland and Centennial Golf Club in nearby Medford.

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