Holiday Rentals in Ashland
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Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
176 rentals in Ashland.
The Ashland Cottage, walk to town
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
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Asian Inspired Escape with View - Just 3 Miles from Downtown
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
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Craftsman Style Home in Country Setting
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
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High Street Cottage Artists' Garden Cottage Clean & Beautiful
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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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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Hanna's House- Your Home Away from Home
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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In the historic railroad district, walking distance to all the best of Ashland!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Walk to town from this Charming Cottage.
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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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The Madrone House, Country Getaway with Panoramic Views
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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The Perfect Vacation Cottage
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stone's Throw Bungalow ~ Walk to Plays, Licensed/Legal, Private Entrance, Garden
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Stunning studio, Italian Motif, Walk to Town.
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
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 3
Match: Sleeps
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BookStayHop - #33 The Cabins on Hyatt Prairie - Sleeps 6 - Hot Tub
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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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Hyatt Lake Mountain Retreat
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
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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ArtYcottage UNBELIEVEABLE...
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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In the Heart of Town, Charming Historic Home, Quintessential Ashland!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stacy's 2nd St Cottage. Steps to downtown.
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Best In Ashland: Magnificent View, Privacy, Quality, Convenience, Very Clean
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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BookStayHop - The Pioneer - Craftsman House - Closest to OSF!
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 4
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Hyatt Prairie Mountain Cabin
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Terra Cottage Inn - Ashland, Oregon
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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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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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BookStayHop - #44 The Cabins on Hyatt Prairie - Sleeps 6 - Hot Tub
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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 3
Match: Sleeps
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ORCHARD SUITE - Private, Safe & Comfortable Getaway! Hot tub, Pet friendly
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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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The Maple Apartment at Tudor House Vacation Rentals
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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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Premier Downstairs Flat in Perfect Down Town Location
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Country Setting, five minute drive to Ashland and a short walk to Emigrant Lake
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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COZY cottage near Lithia Park and Town! Ashland, OR
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Intimate Comfort in a vintage neighborhood 4 blocks walk to Ashland Plaza.
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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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Charming, Comfortable Garden Studio Above The University.
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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BookStayHop - Whispering Pines Cabin Retreat ~ Dog Friendly ~ Full Kitchen
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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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Ashland's new vacation rental.
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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BookStayHop - Blue Moon House ~ Just Five Blocks from OSF!~ Gourmet Kitchen
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
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BookStayHop - #46 The Cabins on Hyatt Prairie - Sleeps 5-Dog Friendly
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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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Spacious B Street Beauty, Around the Corner from Festival
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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BookStayHop - The Pioneer House -North Suite (Upstairs) - Closest to OSF!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Helman Street Penthouse with a View
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Showing results 1-50 of 176
Frequently Asked Questions about Ashland
- Yes, here are some popular holiday rentals in Ashland that have a pool:
- ArtYcottage UNBELIEVEABLE...
- The High Street Cottage An Artists' Garden Cottage
- The Terra Cottage Inn a beautiful Luxury Apartment
- Yes, here are some popular holiday rentals in Ashland that have internet access:
- ArtYcottage UNBELIEVEABLE...
- The High Street Cottage An Artists' Garden Cottage
- The Terra Cottage Inn a beautiful Luxury Apartment
- Some of the most popular kid friendly rentals in Ashland are:
- ArtYcottage UNBELIEVEABLE...
- Abigail's Two Bedroom Vacation Cottage, easy 10-min. walk to plaza/theaters/shop
- 2nd Street Cottages, HERITAGE HOUSE