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Ashland vacation rentals

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Best Ashland vacation rentals

Most recommended vacation rentals in Ashland

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Callahan's Lodge and Restaurant - Ashland - Living room
Callahan's Lodge and Restaurant
Ashland, OR, United States
8.1Very good(93)
Free Wi-Fi
Pet friendly
C$ 224+
Check availability
The Mountain House by WanderLodges - Ashland - Kitchen
The Mountain House by WanderLodges
Ashland, OR, United States
9.6Wonderful(23)
Parking
Free Wi-Fi
C$ 440+
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Charming Retreat: Ashland's Urban Hideaway - Ashland - Living room
Charming Retreat: Ashland's Urban Hideaway
Ashland, OR, United States
Free Wi-Fi
C$ 496+
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Ashland Cabin on 170 Acres with Mtn Views and Sauna! - Ashland - Living room
Ashland Cabin on 170 Acres with Mtn Views and Sauna!
Ashland, OR, United States
8.5Very good(12)
Free Wi-Fi
C$ 433+
Check availability
Mahar Homes - Plaza North on First - Ashland - Living room
Mahar Homes - Plaza North on First
Ashland, OR, United States
9.7Wonderful(2)
Parking
Free Wi-Fi
C$ 736+
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Barclay Klum House by WanderLodges - Ashland - Living room
Barclay Klum House by WanderLodges
Ashland, OR, United States
9.6Wonderful(4)
Parking
Free Wi-Fi
C$ 509+
Check availability
Swank House- West Wing Suite- Pet Friendly - Ashland - Patio
Swank House- West Wing Suite- Pet Friendly
Ashland, OR, United States
9.6Wonderful(14)
Parking
Free Wi-Fi
C$ 256+
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Lakeside escape - Ashland - Kitchen
Lakeside escape
Ashland, OR, United States
Free Wi-Fi
Pet friendly
C$ 370+
Check availability
Lodge Room 1 with Jacuzzi Tub at Green Springs Inn - Ashland - Bedroom
Lodge Room 1 with Jacuzzi Tub at Green Springs Inn
Ashland, OR, United States
C$ 323+
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The Dogwood Suite at Tudor House Vacation Rentals - Ashland - Bedroom
The Dogwood Suite at Tudor House Vacation Rentals
Ashland, OR, United States
Free Wi-Fi
C$ 368+
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Swank House on Main St in Ashland - Ashland - Bedroom
Swank House on Main St in Ashland
Ashland, OR, United States
10Wonderful(3)
Parking
Free Wi-Fi
C$ 769+
Check availability
Hanna's House by WanderLodges - Ashland - Bedroom
Hanna's House by WanderLodges
Ashland, OR, United States
9.8Wonderful(11)
Parking
Free Wi-Fi
C$ 339+
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Studio with King-Size Bed - Ashland
Studio with King-Size Bed
Ashland, OR, United States
9.6Wonderful(22)
Parking
Free Wi-Fi
Pet friendly
C$ 170+
Check availability
Second Street Cottages - Ashland
Second Street Cottages
Ashland, OR, United States
9.7Wonderful(167)
Parking
Free Wi-Fi
C$ 284+
Check availability
Beautiful Apartment in Ashland - Ashland
Beautiful Apartment in Ashland
Ashland, OR, United States
Free Wi-Fi
C$ 300+
Check availability
1 Month Minimum Upstairs Apartment in Victorian House - Ashland
1 Month Minimum Upstairs Apartment in Victorian House
Ashland, OR, United States
C$ 83+
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KAYAK's top tips for finding Ashland holiday rental deals

  • Pet friendly is the most popular vacation rental property amenity in Ashland
  • Vacation rentals in Ashland are around 4% cheaper than hotels on average. Search here to compare prices for all accommodation types in Ashland.
  • The best vacation rental properties in Ashland are Mt Ashland Log Cabin, Ski Area 10mi, Ashland 10mi, Swedish sauna, by Pacific CTr (10.0, 32 reviews), 232 4th Street (10.0, 29), and In the historic railroad district, walking distance to all the best of Ashland! (9.9, 54), based on ratings and reviews from real travelers.
  • Downtown is the neighborhood in Ashland with the most affordable vacation rental properties (6 properties with an average price of C$ 505 per night). 1907 Charmer, Perfect Downtown Location, So Clean!, East Main Downtown Bungalow, and Spacious B Street Beauty, Around the Corner from Festival are the most popular rental properties in Downtown.
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FAQs when booking a vacation home in Ashland

  • What types of vacation rentals are available in Ashland?

    There are loads of different property types that you can make your vacation home in Ashland. You’ll find agritourism, apartments, bungalows, cabins, caravans, castles, chalets, cottages, houses, homestays, lodges, ranches, safari/tentalows and villas.

  • What are some of the most-loved vacation rentals available in Ashland?

    If you’re looking for something special, the vacation rental most loved by KAYAK users is Callahan's Lodge and Restaurant.

  • Are there any pet-friendly vacation rentals in Ashland?

    There are a number of dog and pet-friendly Ashland vacation rentals, with around 13% allowing you to bring your pet along with you.

  • How can I find vacation rentals near me in Ashland?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

See more FAQs

Where to stay in Ashland?

Our map will help you find the perfect place to stay in Ashland by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Ashland

Ashland vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Ashland. Find cheap vacation homes to rent in Ashland. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Ashland that suits you best.

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