Vacation Rentals in Ashland, Oregon

50 Properties Available

2 bedrooms, office with sofa bed, sofa bed in living room, 3 bathrooms Lodge
2 bedrooms, office with sofa bed, sofa bed in living room, 3 bathrooms
$1161 / night
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Come stay at our farmhouse! A place to integrate all the beauty surrounding you! Agritourism
Come stay at our farmhouse! A place to integrate all the beauty surrounding you!
$853 / night
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Luxury Ashland Mountain Escape: Pool, Hot Tub Villa
Luxury Ashland Mountain Escape: Pool, Hot Tub
$799 / night
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5 bedroom historic home with brand new furnishings, and is perfect for up to 14 guests. Apartment
5 bedroom historic home with brand new furnishings, and is perfect for up to 14 guests.
$787 / night
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Alley-By Loft: Smack Dab in the Middle of Ashland! Steps from Theaters & Lithia Condo
Alley-By Loft: Smack Dab in the Middle of Ashland! Steps from Theaters & Lithia
$666 / night
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Family Bliss: Pool, Hot Tub, Gym, Sauna Private vacation home
Family Bliss: Pool, Hot Tub, Gym, Sauna
$629 / night
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In the historic railroad district, walking distance to all the best of Ashland! Private vacation home
In the historic railroad district, walking distance to all the best of Ashland!
$540 / night
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The Victorian Secret - Just Steps to Theaters, Plaza, Restaurants & Park. ENJOY! Private vacation home
The Victorian Secret - Just Steps to Theaters, Plaza, Restaurants & Park. ENJOY!
$503 / night
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Sunset Chalet - 2300 sq.ft. Multi-Seasonal retreat only15 minutes from Ashland ! Chalet
Sunset Chalet - 2300 sq.ft. Multi-Seasonal retreat only15 minutes from Ashland !
$493 / night
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Cabin in the mountains of Ashland Apartment
Cabin in the mountains of Ashland
$370 / night
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1907 Charmer, Perfect Downtown Location, So Clean! Private vacation home
1907 Charmer, Perfect Downtown Location, So Clean!
$362 / night
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Callahan's House Mobile home
Callahan's House
$359 / night
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Central Serenity: 3BDR City Escape Private vacation home
Central Serenity: 3BDR City Escape
$355 / night
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Abbott's Cottages- The Raven. Two bedroom cottage just two blocks to downtown. Cottage
Abbott's Cottages- The Raven. Two bedroom cottage just two blocks to downtown.
$321 / night
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Mayfield Gardens Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn Cabin
Mayfield Gardens Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
$300 / night
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Mt. Ashland Home, Ski Area 10mi, Ashland 10mi, Swedish sauna, by Pacific C.Trail Private vacation home
Mt. Ashland Home, Ski Area 10mi, Ashland 10mi, Swedish sauna, by Pacific C.Trail
$299 / night
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Stacy's 2nd St Cottage. Steps to downtown. Cottage
Stacy's 2nd St Cottage. Steps to downtown.
$295 / night
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The Ashland Cottage, walk to town Cottage
The Ashland Cottage, walk to town
$293 / night
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Hyatt Prairie Mountain Cabin Private vacation home
Hyatt Prairie Mountain Cabin
$281 / night
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Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette. Private vacation home
Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette.
$252 / night
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Charming 1 BR Orliena Suite in historic downtown Ashland, OR. Walk to the Oregon Shakespeare Festival, shops, and dining. Features a kitchenette, plush queen bed, and shared hot tub access. Dog friendly! Apartment
Charming 1 BR Orliena Suite in historic downtown Ashland, OR. Walk to the Oregon Shakespeare Festival, shops, and dining. Features a kitchenette, plush queen bed, and shared hot tub access. Dog friendly!
$250 / night
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Ashland's Premier Eco-B&B: Dog-friendly King Bed Suite with Separate Entrance (Jardin) Bed & breakfast
Ashland's Premier Eco-B&B: Dog-friendly King Bed Suite with Separate Entrance (Jardin)
$243 / night
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The Peerless Hotel | Anniversary Suite #3 | Twin Soaking Tubs | Historic District Apartment
The Peerless Hotel | Anniversary Suite #3 | Twin Soaking Tubs | Historic District
$234 / night
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Oak Hill Bed & Breakfast Bed & breakfast
Oak Hill Bed & Breakfast
$232 / night
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Chateau Herbe ~ Oberon Suite w/ Kitchen Apartment
Chateau Herbe ~ Oberon Suite w/ Kitchen
$226 / night
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Peaceful, spacious home on 8 acres. Pet-friendly, close to town, and a creek! Private vacation home
Peaceful, spacious home on 8 acres. Pet-friendly, close to town, and a creek!
$218 / night
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Custom Ashland Home with Fantastic Mountain Views Private vacation home
Custom Ashland Home with Fantastic Mountain Views
$210 / night
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Lodge Room 4 with Jacuzzi Tub at Green Springs Inn Hotel
Lodge Room 4 with Jacuzzi Tub at Green Springs Inn
$207 / night
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Beautiful little place. Walk to town and theaters! Private vacation home
Beautiful little place. Walk to town and theaters!
$205 / night
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The Dogwood Suite at Tudor House Vacation Rentals Apartment
The Dogwood Suite at Tudor House Vacation Rentals
$197 / night
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Ashland Cabin on 170 Acres w\/ Mtn Views & Sauna! Cabin
Ashland Cabin on 170 Acres w\/ Mtn Views & Sauna!
$196 / night
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Luxuriously comfortable & peaceful getaway downtown Ashland, with views. Apartment
Luxuriously comfortable & peaceful getaway downtown Ashland, with views.
$195 / night
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The Bard's Inn, BW Signature Collection by Best Western Hotel
The Bard's Inn, BW Signature Collection by Best Western
$190 / night
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Sage Ashland Cottage Cottage
Sage Ashland Cottage
$186 / night
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The Maple Apartment at Tudor House Vacation Rentals Apartment
The Maple Apartment at Tudor House Vacation Rentals
$170 / night
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Best Western Windsor Inn Hotel
Best Western Windsor Inn
$160 / night
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Monthly rental offering privacy and views near Ashland Plaza. Private vacation home
Monthly rental offering privacy and views near Ashland Plaza.
$160 / night
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Charming well appointed Cottage in Ashland ( 800 + sq. ft. ) Cottage
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
$150 / night
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Exquisite Artist's home, all summer or month to month. Private vacation home
Exquisite Artist's home, all summer or month to month.
$147 / night
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Ashland Hills Hotel & Suites Hotel
Ashland Hills Hotel & Suites
$142 / night
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Comfort Inn & Suites Hotel
Comfort Inn & Suites
$128 / night
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Flagship Inn of Ashland Hotel
Flagship Inn of Ashland
$126 / night
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Ashland Boho-Chic with a Yard Apartment
Ashland Boho-Chic with a Yard
$120 / night
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Green Springs Inn Hotel resort
Green Springs Inn
$104 / night
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Stratford Inn Hotel
Stratford Inn
$100 / night
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Charming 2-bedroom townhome in serene Ashland with hot tub and fireplace Private vacation home
Charming 2-bedroom townhome in serene Ashland with hot tub and fireplace
$83 / night
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Available again in September! Spacious Historic House one block to Town! Private vacation home
Available again in September! Spacious Historic House one block to Town!
$62 / night
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Ashland Lodge w\/ Lake Views & Game Room Loft Cottage
Ashland Lodge w\/ Lake Views & Game Room Loft
$0 / night
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Beautiful New Studio in the Hills of Ashland Apartment
Beautiful New Studio in the Hills of Ashland
$0 / night
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Brand New Crowson Cottage Private vacation home
Brand New Crowson Cottage
$0 / night
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