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Ashland
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    Ashland Holiday Rentals

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      Travellers to Ashland are booking June dates now. Secure your holiday rental today, and have the perfect trip.
      All 70 Rentals in Ashland
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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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      Pioneer House (Rear Home) ~ One Block from OSF1 / 22
      3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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      Singing Birds Cabin1 / 15
      (23)Excellent
      2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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      Hound's Landing Cottage #A ~ A 'dog's walk' to OSF1 / 16
      2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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      About this property
      This home is not just pet-friendly, but pet-welcoming. This beautifully restored Farm House is divided into a two suite home a short walk from the Oregon Shakespeare Festival and the joys of downtown Ashland. With a king sized bed in the bedroom and a twin and queen upstairs. (and a bed for your...
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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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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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      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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      (#33) Cabin at Hyatt Lake - Sleeps 6 - Hot Tub1 / 11
      2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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      • Mountain Views
      • Cable/satellite TV
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      • Hot Tub
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      • Waterfront
      • Central Heating
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      Suitability
      Pet friendly
      Kid friendly
      Smoking allowed
      About this property
      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 the forest, and pocket views of Hyatt Lake. It's just a few minute walk down to the water! The master bedroom has a queen size...
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      Ashland, Oregon 97520
      Cabin Holiday Rental - 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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      About this property
      (NOTE: Listed through the City of Ashland as Oak Street Cottages) The home features a full kitchen, generous living room with fireplace, flat panel television, a patio with BBQ and seating, two private bedrooms, full bathroom, and enough sleeping space to accommodate up to 6 guests. The cottage...
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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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      Carlisle Garden Suites - Chamomile1 / 15
      1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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      • Wi-Fi
      • Private Garden
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      About this property
      Nine luxury cottages and suites surround an exquisite tranquil garden. All units have private entrances, kitchenettes, luxury baths, free WI-FI, A/C and ceiling fans, morning pastries and coffee, and free parking. Queen and King bed units, some with additional daybeds. All king suites can be...
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      Ashland, Oregon 97520
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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      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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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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      The High Street Cottage An Artists' Garden Cottage1 / 10
      (7)Excellent
      2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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      • Washer
      • Porch
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      Pet friendly
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      Smoking allowed
      The Unique High Street Cottage
      Reviewed 24 March 2018
      The columnist Herb Caen wrote of the San Franciscan native who died and went to Heaven. Saint Peter met him at the Pearly Gates and gave him a tour of his new eternal home. When...
      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...
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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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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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      (#39) Cabin at Hyatt Lake - Sleeps Six - Hot Tub1 / 12
      2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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      • Hot Tub
      • Wi-Fi
      • DVD Player
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      • Central Heating
      • Mountain Views
      • Grill
      • Cable/satellite TV
      Suitability
      Pet friendly
      Kid friendly
      Smoking allowed
      About this property
      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 forest! The master bedroom has a queen bed, and the loft has two full beds. There is a full kitchen, a new bbq, and one full bathroom....
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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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      Hopyard View Farm - Minutes to Downtown Ashland!1 / 25
      (1)Very good
      2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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      • Private Garden
      • Central Heating
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      • Mountain Views
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      Pet friendly
      Kid friendly
      Smoking allowed
      Quiet, rural, 5 minutes to downtown Ashland
      Reviewed 1 September 2017
      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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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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      (#46) Cabin at Hyatt Lake - Sleeps 4 - Hot Tub1 / 9
      2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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      • Patio
      • Cable/satellite TV
      • Central Heating
      • Wi-Fi
      • DVD Player
      • Hot Tub
      • Mountain Views
      • Grill
      Suitability
      Pet friendly
      Kid friendly
      Smoking allowed
      About this property
      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 Mount Ashland! The bedroom has a queen bed, and the loft has both full and single beds. There is a full kitchen, sofa, chair, a...
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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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      Whispering Pines Cabin at Hyatt Lake ~ Sleeps 8 ~ Pet Friendly1 / 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
      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! Two story, three bedrooms (master downstairs / upstairs dormitory style), one and one half baths, hardwood flooring, large...
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      Ashland, Oregon 97520
      Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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      (#44) Cabin at Hyatt Lake - Sleeps Six - Hot Tub1 / 13
      2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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      • Hot Tub
      • Parking
      • Cable/satellite TV
      • Mountain Views
      • DVD Player
      • Central Heating
      • Grill
      • Wi-Fi
      Suitability
      Pet friendly
      Kid friendly
      Smoking allowed
      About this property
      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 of Mount Ashland! The bedroom has a queen bed, and the loft has two full beds. There is a full kitchen, sectional sofa, futon,...
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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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      Carlisle Garden Suites - Calla Suite1 / 16
      1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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      • Air Conditioning
      • Wi-Fi
      • Private Garden
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      Pet friendly
      Kid friendly
      Smoking allowed
      About this property
      Nine luxury cottages and suites surround an exquisite tranquil garden. All units have private entrances, kitchenettes, luxury baths, free WI-FI, A/C and ceiling fans, morning pastries and coffee, and free parking. Queen and King bed units, some with additional daybeds. All king suites can be...
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      Ashland, Oregon 97520
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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      ArtYcottage UNBELIEVEABLE...1 / 16
      (17)Excellent
      2 Bedrooms, 2 Bathrooms, 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
      This is a magical artisan hideaway.
      Reviewed 13 August 2016
      We had a remarkable time here as we celebrated grandma's 80th birthday with 3 generations of daughters. The pictures did not prepare us for the utter beauty of the cottage and...
      An Oregon"must see!"
      Reviewed 14 September 2015
      What really sets this cottage apart from many you may have rented is that the owners have hand crafted and built every inch of the inside and outside. It is artistry and...
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      About this property
      Welcome to the Artycottage nestled in the Cascade foothills, minutes from downtown Ashland, Oregon, home of the Oregon Shakespeare Festival and Saydah Design. All of the work in the Artycottage is made by Saydah Design and can be ordered. Come stay for a weekend or a week and experience...
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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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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      • Cable/satellite TV
      • Wi-Fi
      • Mountain Views
      • Secure Parking
      • Outdoor Dining Area
      • Air Conditioning
      • Shared Garden
      Suitability
      Pet friendly
      Kid friendly
      Smoking allowed
      Great Place!
      Reviewed 24 September 2015
      Beautiful spot, wonderful cottage, perfect for the four of us. Less than a 5 minute drive to down town Ashland with it's fabulous plays, restaurants and shopping. Lovely new...
      Cute place
      Reviewed 6 May 2015
      Abigail's has new owners, who we found to be friendly and helpful. Super clean cottage, walked to plays two times a day. Great time
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      About this property
      Abigail's Cottage within walking distance to the city center, is licensed by the city of Ashland (Business License #007411 & Planning Action #06-275) and Jackson County, (#1581566C) and meets required health, safety and fire codes. Comfortable two bedroom 1 1/2 bath cottage, completely renovated...
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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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      (#32) Cabin at Hyatt Lake - Sleeps 6 - Hot Tub1 / 10
      2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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      • Central Heating
      • Cable/satellite TV
      • DVD Player
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      • Waterfront
      • Hot Tub
      • Patio
      • Mountain Views
      Suitability
      Pet friendly
      Kid friendly
      Smoking allowed
      About this property
      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 of Hyatt Lake. It's just a few minute walk down to the water! The master bedroom has a queen size bed, and the loft has two...
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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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      (#52) Hyatt Lake Cabin ~ Sleeps 4 ~ Direct Lake View1 / 14
      (1)Excellent
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      • Parking
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      • Mountain Views
      Suitability
      Pet friendly
      Kid friendly
      Smoking allowed
      Peaceful and tranquil surroundings and beautiful clean cabin
      Reviewed 4 January 2018
      I just loved this cabin with everything else around it. we went there in Dec when it snowed and we loved it. Beautiful drive from Ashland, with lots of beautiful sceneries to...
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      About this property
      Views of Hyatt Lake, the Steel Trestle Bridge, the surrounding Alpine Forest... and just eighteen miles from downtown Ashland! Outside, the Huge Covered Deck has a Double Hammock and Outdoor Dining! Inside the Sleeping Loft has a Queen Bed. The Living Room has a Queen Sectional Sleeper Sofa and 40'...
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      Ashland, Oregon 97520
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Art & Garden Cottage ~ Minutes from Downtown Ashland1 / 17
      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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      Ashland, Oregon 97520
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Butler's Quarters ~ Downtown Ashland (Private Entry)1 / 9
      Studio, 1 Bathroom, Sleeps 2 Quick View
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      About this property
      PRIVATE ENTRY AND PARKING The single, private bedroom has a queen bed and private bathroom with shower. Flat-panel TV, with free cable and wi-fi. A mini-fridge, microwave, and Keurig coffee maker are also available for your comfort. The courtyard is beautifully furnished and has a beautiful shared...
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      Ashland, Oregon 97520
      Condo/Apartment - 1 Bathroom, Sleeps 2
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      Walk to Downtown/Theaters from this Charming Home1 / 8
      2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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      About this property
      Welcome to the Victorian Rose at Blossom View Cottages. We are located in the historic railroad district, less than half a mile from theaters, Plaza and Downtown. Let this charming, historic home fill you with a sense of well-being and luxury. There are two bedrooms, each with a queen bed, and a...
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      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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      RedTail Inn ~ The 'Red' McCall Suite ~ Sleeps Six1 / 18
      (1)Excellent
      2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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      • Mountain Views
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      Pet friendly
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      Smoking allowed
      Perfect Getaway!
      Reviewed 3 weeks ago
      Absolutely love this place!! The rooms were super inviting, clean and comfy (especially the bed!). The owners thought of everything (even stocking the place with great local...
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      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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      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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      • Wi-Fi
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      • Cable/satellite TV
      • DVD Player
      • Patio
      • Housekeeping Included
      • Grill
      • Balcony
      Suitability
      Pet friendly
      Kid friendly
      Smoking allowed
      About this property
      (NOTE: Listed through the City of Ashland as Oak Street Cottages) Built in the late 1800's, the Sherwin House is located in the heart of Downtown Ashland and is one of the closest properties to the famed Oregon Shakespeare Festival, at just one and half blocks to the entry of the Theaters....
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      Ashland, Oregon 97520
      Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 11
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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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      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! Our second-floor studio...
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      Location Information
      Ashland, Oregon 97520
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Stone's Throw Bungalow - Licensed, Private Garden1 / 23
      Studio, 1 Bathroom, Sleeps 2 Quick View
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      • Wi-Fi
      • Private Garden
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      Pet friendly
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      Smoking allowed
      About this property
      Just a stone's throw to the plaza, a licensed one-bedroom vacation rental suite is tucked behind one of Ashland's charming craftsman-style bungalows. Your private gated entrance, located behind the house, opens onto a peaceful garden and quaint patio - a wonderful place to enjoy morning coffee and...
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      Ashland, Oregon 97520
      Condo/Apartment - 1 Bathroom, Sleeps 2
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      Pioneer House(Lower Home)-Closest Home to OSF1 / 19
      3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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      • Washer
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      Pet friendly
      Kid friendly
      Smoking allowed
      About this property
      COMING THIS SPRING! This home has being fully renovated...from the studs out... with all new furnishings! This is the closest vacation home to the Oregon Shakespeare Festival. Only one full block separates the house from the main entrance to the theaters. This spacious three bedroom historic...
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      Ashland, Oregon 97520
      Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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      RedTail Inn ~ The Orliena McCall Suite ~ Sleeps Four1 / 19
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      • Patio
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      • Mountain Views
      • Air Conditioning
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      Suitability
      Pet friendly
      Kid friendly
      Smoking allowed
      About this property
      A 1900's Classic Farmhouse REBORN! Red Tail ... Downtown Ashland's Luxury Boutique Inn Enjoy your four block walk to Oregon's Shakespeare Festival as you pass local Coffee Bars, Shops, and Restaurants Furnishings mix Modern Farmhouse style with Art Nouveau accents. Linens are made in the...
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      Ashland, Oregon 97520
      Holiday Rental House - 1 Bedroom, 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
      • Cable/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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      Bel Canto ~ Ashland Hillside ~ Five Minutes from OSF1 / 17
      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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      Lori Lanes 'Juliet Cottage' ~ 2 Bedroom ~ Downtown1 / 12
      2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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      About this property
      Completely renovated, and just a half dozen blocks from Downtown Ashland and the Oregon Shakespeare Festival! This cottage has two private bedrooms, with a queen bed in each. The bathroom has an oversize walk-in shower, great for those with physical limitations. The common area features a 32' flat...
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      Location Information
      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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      Pioneer House(Upper Floor)-Closest Property to OSF1 / 6
      2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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      • Patio
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      • Terrace
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      Kid friendly
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      About this property
      COMING THIS SPRING! This home has being fully renovated...from the studs out... with all new furnishings! This is the closest vacation home to the Oregon Shakespeare Festival. Only one full block separates the house from the main entrance to the theaters. There are two private bedrooms, both...
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      Location Information
      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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      Hound's Landing Cottage #B ~ A 'dog's walk' to OSF1 / 15
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      About this property
      This home is not just pet-friendly, but pet-welcoming. This beautifully restored Farm House has been divided into a two suite vacation home just a short walk from the Oregon Shakespeare Festival and the joys of downtown Ashland. With a queen sized bed in the bedroom and a sofa bed in the living...
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      Location Information
      Ashland, Oregon 97520
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Blue Moon Cottage ~ Pet Friendly ~ 5 Blocks to OSF1 / 13
      1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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      About this property
      The Blue Moon Cottage is attached to the main home but has two private entrances. It offers a full kitchen, a gas fireplace, air conditioning, a separate bedroom with a comfy queen bed, a full bath with shower/tub combination and a private patio. There is also a flat screen television in the living...
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      Location Information
      Ashland, Oregon 97520
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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      Lori Lanes 'Romeo Cottage' ~ 2 Bedroom ~ Downtown1 / 15
      2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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      Pet friendly
      Kid friendly
      Smoking allowed
      About this property
      Completely renovated, and just a half dozen blocks from Downtown Ashland and the Oregon Shakespeare Festival! This cottage has two private bedrooms, with a queen bed in each. The bathroom has an oversize walk-in shower, great for those with physical limitations. The common area features a 32'...
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      Location Information
      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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      'C' Street Station1 / 31
      1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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      About this property
      NEW and PROFESSIONALLY DESIGNED! Tucked in Downtown Ashland's Historic Railroad District and just a ten to fifteen minute walk to the Oregon Shakespeare Festival. 'C' Street Station is new... from the ground up! This studio home features a luxurious king bed, fireplace, flat screen smart TV,...
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      Location Information
      Ashland, Oregon 97520
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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      Location Information
      Ashland, Oregon 97520
      Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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      RedTail Inn ~ The Louisa McCall Suite ~ Sleeps Two1 / 16
      Studio, 1 Bathroom, Sleeps 2 Quick View
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      • Mountain Views
      • Cable/satellite TV
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      • Terrace
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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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      Location Information
      Ashland, Oregon 97520
      Condo/Apartment - 1 Bathroom, Sleeps 2
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      Sunset Chalet - 2600 sq.ft. Multi-Seasonal retreat1 / 29
      3 Bedrooms, 2 Bathrooms, Sleeps 15 Quick View
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      • DVD Player
      • Mountain Views
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      • Housekeeping Included
      • Hot Tub
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      Pet friendly
      Kid friendly
      Smoking allowed
      About this property
      3 story chalet nestled in the Cascade Mountains at 4000' elevation. Fantastic view overlooking Siskiyou Mtns, Klamath Mtns, Colestine Valley and Mt. Ashland. Awesome sunsets! Perfect for hikers, bikers (dozens of trails from Mt. Ashland down to city of Ashland), skiers (Mt. Ashland Lodge is 15...
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      Location Information
      Ashland, Oregon 97520
      Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 15
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      *NEW* Blue Moon House ~ Just Five Blocks from OSF!1 / 28
      5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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      • Cable/satellite TV
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      Pet friendly
      Kid friendly
      Smoking allowed
      About this property
      Just five blocks from the Oregon Shakespeare Festival in a historic Ashland neighborhood... Built in the early 1900's and fully renovated the Blue Moon House has it all! Five bedrooms, each with it's own private bathroom. A gourmet kitchen with a large dining area, a living area with a fireplace,...
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      Location Information
      Ashland, Oregon 97520
      Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 11
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      #49 Hyatt Lake Cabin - Sleeps 3 - Private Cabin1 / 17
      1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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      About this property
      Just eighteen miles east of Ashland! Welcome to your Hyatt Lake Cabin! The master bedroom has a queen size bed, and the living room has a sectional sofa to sleep an extra guest. Full kitchen, dining room, and bathroom. The cabin has an (electric) wood stove, 'smart' tv, dvd player, satellite tv,...
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      Location Information
      Ashland, Oregon 97520
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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      Mountain Pine Cabin - Pet Friendly1 / 25
      2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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      NEW! You've just found your mountain dream...and just 20 miles from downtown Ashland! Mountain Pine Cabin sits on a wooded acre of land, with views of Hyatt Lake from the deck and dining room. Your home features a full kitchen, great room with a sofa and love seat, as well as a 55' Smart TV, WiFi,...
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      Location Information
      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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      (#40) Cabin at Hyatt Lake - Sleeps Six - Hot Tub - Pet Friendly1 / 10
      2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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      • Cable/satellite TV
      • Mountain Views
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      Pet friendly
      Kid friendly
      Smoking allowed
      About this property
      *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 forest. The master bedroom has a queen bed, and the loft has two full beds. There is a full kitchen, a new bbq, and one full...
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      Location Information
      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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      (#51) Hyatt Lake Cabin ~ Sleeps 6 ~ Hot Tub ~ Lake Views1 / 10
      2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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      • Mountain Views
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      Pet friendly
      Kid friendly
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      About this property
      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! **Enjoy the New Hot Tub** The Master Bedroom has a Queen Bed. The Sleeping Loft has a Queen Bed and Full Bed. The Living...
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      Location Information
      Ashland, Oregon 97520
      Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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
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      • Hot Tub
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      • Outdoor Dining Area
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      Pet friendly
      Kid friendly
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      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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      Location Information
      Ashland, Oregon 97520
      Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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      '1900' Guest House ~ Downtown Ashland ~ Near Oregon Shakespeare Festival!1 / 9
      1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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      About this property
      The Historic '1900' Guest House is the best of Downtown Ashland! Close to restaurants and retailers... and less than five blocks to the Oregon Shakespeare Festival. In a quiet residential neighborhood, our home features a bedroom with king size bed, a bathroom (shower), a complete kitchen with...
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      Location Information
      Ashland, Oregon 97520
      Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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      Anne Hathaway House1 / 31
      6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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      Pet friendly
      Kid friendly
      Smoking allowed
      About this property
      The Anne Hathaway House was built in 1908 as a boarding house for travelers. David and Deedie Runkel purchased the home in 2002 and continue to operate it today. Located just four short blocks from the Oregon Shakespeare Festival, the Anne Hathaway House is ideal for large groups of theater goers,...
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      Location Information
      Ashland, Oregon 97520
      Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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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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      • Waterfront
      • Parking
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      Pet friendly
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      Smoking allowed
      Stunning vacation cabin in spectacular private location
      Reviewed 20 April 2017
      Our family thoroughly enjoyed our stay at this stunning vacation cabin located in an area that provided plenty of privacy. The Guest Contact person, Eliasar, who greeted us upon...
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      About this property
      Have a truly memorable trip to Oregon when you stay at this gorgeous 4-bedroom, 3-bathroom Ashland home, which sleeps 13. Enjoy the best of outdoor living with a private fishing pond and plenty of patio space with spectacular views! THE PROPERTY This Ashland vacation rental home is an ideal...
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      Location Information
      Ashland, Oregon 97520
      Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 13
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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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      1
      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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