Ashland Holiday Rentals
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208 rentals in Ashland.
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#32 & #33 Hyatt Prairie Compound - Hot Tub- Sleeps 12- Kitchen
Cabin Holiday Rental
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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The Ashland Cottage, walk to town
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Craftsman Style Home In Country Setting
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Brand New Custom Ashland Home with Fantastic Mountain Views
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Steps to theatres, restaurants, shops, nightlife in historic railroad district
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stacy's 2nd St Cottages .. Steps to theaters, Lithia Park and downtown Ashland
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Hanna's House- Your Home Away from Home
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Railroad District, steps to downtown, everything you need to enjoy Ashland!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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The Madrone House, New Country Getaway with Panoramic Views
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Charming historic cottage just 4 blocks from downtown (Licensed PA 17-248)
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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High Street Cottage Artists' Garden Cottage Clean & Beautiful
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Maple Apartment at Tudor House Vacation Rentals
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Hyatt Lake Mountain Retreat
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Hyatt Praire Mountain Cabin
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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ArtYcottage UNBELIEVEABLE...
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Asian Inspired Escape with View - Just 3 Miles from Downtown
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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#33 The Cabins at Hyatt Lake - Sleeps 6 - Hot Tub
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Perfect Vacation Cottage
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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The Aloha House ~ Hot Tub & Seasonal Pool
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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'Orchard Suite' Stay...Relax...Enjoy
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Brand New Guesthouse - 15-Minute Easy Walk to Theaters, Plaza; Historic Ashland
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Vineyard Home w/ 360 Views, private walking, pet-friendly, 2 miles from town!
Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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The Best In Ashland: Magnificent View, Privacy, Quality, Convenience, Very Clean
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 10
Match: Sleeps
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BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Terra Cottage Inn a beautiful Luxury Apartment
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Helman House-Three Blocks from the Oregon Shakespeare Festival
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Big Discounts 2020! Walk to town from this Charming Cottage.
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Winter on PINE STREET! ASHLAND! COZY cottage near Lithia Park and Town!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Pioneer - Craftsman House - Closest to OSF!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Space Next to Everything, Walk Anywhere!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Welcome to clean air, space and relaxation in SE Ashland!
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Mt. Ashland Homestead's Secluded Forest House, 15 minutes from Ashland
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Quiet and peaceful cottage close to downtown
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps
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Private Suite Near Shakespeare
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Dogwood Suite at Tudor House Vacation Rentals
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps
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BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den Near Theaters, Downtown
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Zen Atmosphere Studio Cottage. Private Entrance & Healing Garden. Walk to Plays
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Abigail's Two Bedroom Vacation Cottage, easy 10-min. walk to plaza/theaters/shop
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Whispering Pines Cabin Retreat ~ Dog Friendly
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming, Comfortable Garden Studio Above The University.
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Ashland Cabin - 170 Acres w/Mountain Views & Sauna
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The High Street Cottage An Artists' Garden Cottage
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Hyatt Prairie Mountain Cabin
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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ArtYCottage - custom furniture and art through out. Secluded and fabulous!
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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#44 The Cabins at Hyatt Lake - Sleeps 6 - Hot Tub
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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2 bedroom, Modern, Up Scale House, Walk to Town
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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#46 The Cabins at Hyatt Lake-Sleeps 5-Dog Friendly
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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The Pioneer House -North Suite (Upstairs) - Closest to OSF!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Frequently Asked Questions about Ashland
- Yes, here are some popular holiday rentals in Ashland that have a pool:\n
- \n
- The Aloha House ~ Hot Tub & Seasonal Pool \n
- The Aloha House ~ Hot Tub & Seasonal Pool \n
- Gorgeous Views! Stratford Inn Hotel in Ashland Oregon | Affordable Extended Stay \n
- Yes, here are some popular holiday rentals in Ashland that have internet access:\n
- \n
- ArtYcottage UNBELIEVEABLE... \n
- Abigail's Two Bedroom Vacation Cottage, easy 10-min. walk to plaza/theaters/shop \n
- The High Street Cottage An Artists' Garden Cottage \n
- The best pet friendly rentals in Ashland are:\n\nSee all pet friendly holiday rentals in Ashland on Tripadvisor
- Some of the most popular kid friendly rentals in Ashland are:\n
- \n
- ArtYcottage UNBELIEVEABLE... \n
- Abigail's Two Bedroom Vacation Cottage, easy 10-min. walk to plaza/theaters/shop \n
- Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In The Heart Of Ashland \n