As the home of the famed Oregon Shakespeare Festival, Ashland is a charming mountain town with a laid-back vibe and some quaint vacation homes boasting incredible views. Consider these neighborhoods as you look for a place to stay in Ashland.

Top vacation rentals in Ashland

Interior
5.0
Outstanding(186 Reviews)
The Ashland Cottage, walk to town
Cottage
 in Ashland
4 guests · 2 bedrooms · 2 baths
Garden · Kitchen or Kitchenette · Air conditioner

Looking for a memorable stay in Ashland? Our Cottage might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more during your stay.

$$$$
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4.2
Excellent(562 Reviews)
Flagship Inn of Ashland
Motel
 in Ashland
2 queen beds
Garden · Pool · Kitchen or Kitchenette

Motel in Ashland, for $100 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

$$$$
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Lobby or reception
4.1
Excellent(1,290 Reviews)
Timbers INN and Suites
Motel
 in Ashland
1 queen bed
Pool · Pets allowed · Kitchen or Kitchenette

Enjoy the best of Ashland in our Motel, Timbers INN and Suites. A stunning property with amenities including Air conditioner, Internet / Wifi and Pets allowed, and more.

$$$$
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Property view
3.9
Good(612 Reviews)
Plaza Inn & Suites at Ashland Creek
Hotel
 in Ashland
4star
1 king bed
Garden · Pets allowed · Kitchen or Kitchenette

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Ashland, at $117 per night for your next great vacation.

$$$$
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Vacation rentals with air conditioning in Ashland

Fridge, microwave, oven, stovetop
5.0
Outstanding(134 Reviews)
Railroad District, steps to downtown, everything you need to enjoy Ashland!
House
 in Ashland
5 guests · 2 bedrooms · 2 baths
Garden · Kitchen or Kitchenette · Air conditioner

Looking for a memorable stay in Ashland? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more during your stay.

$$$$
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Property grounds
5.0
Outstanding(173 Reviews)
In the historic railroad district, walking distance to all the best of Ashland!
House
 in Ashland
8 guests · 4 bedrooms · 3 baths
Garden · Kitchen or Kitchenette · Air conditioner

Looking for a memorable stay in Ashland? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more during your stay.

$$$$
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Lobby or reception
4.1
Excellent(484 Reviews)
Ashland Hills Hotel & Suites
Hotel
 in Ashland
3star
1 king bed
Garden · Pool · Pets allowed

Looking to create some memories in Ashland? Look no further than our Hotel, Ashland Hills Hotel & Suites. Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Property building
4.0
Good(141 Reviews)
Scottish Inns Ashland
Motel
 in Ashland
1 king bed
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

This Motel in Ashland, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$
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Ashland

Ashland travel guide

Let us help you plan your perfect Ashland vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Ashland, and more.

Frequently asked questions

What are the most popular vacation rental amenities in Ashland?

  • Air conditioner
  • Internet / Wifi
  • Kitchen or Kitchenette

About Ashland

As a relatively small town, Ashland's neighborhood designations are somewhat informal, but they can still help you know which rental locations align with your vacation goals.
  • Shakespeare Blocks/Downtown: Located in the heart of everything, these neighborhoods are best for folks who are in town just to see some plays during the festival.
  • Above the Boulevard: Siskiyou Boulevard is a literal and figurative dividing line in Ashland. Houses "above" (to the northeast) the boulevard are generally tonier and offer better views, though they are farther away from the action in town.
  • Lithia Park: Though it isn't above the boulevard, this part of town balances upscale architecture with proximity to the Angus Bowmer Theatre.

What is the price range for rentals in Ashland?

Vacation rentals in Ashland have a price range between $56-$1,114. The average price for rentals in Ashland is $173 per night.

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