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.

Ashland, OR Vacation Rentals

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

9.9 / 10

Outstanding(231 Ratings)

The Ashland Cottage, walk to town

Cottage

in Ashland

4 guests · 1 bedroom · 1 bath

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

$$$$

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8.3 / 10

Excellent(964 Ratings)

Timbers INN and Suites

Motel

in Ashland

2 guests · 1 bedroom · 1 bath

Enjoy the best of Ashland in our Motel, Timbers INN and Suites. A stunning property with amenities including ;, and more.

$$$$

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8.5 / 10

Excellent(1,357 Ratings)

Stratford Inn

Hotel

in Ashland

3star

2 guests · 1 bedroom · 1 bath

Looking for a memorable stay in Ashland? Our Hotel might just be what you're looking for. Enjoy amenities including ;, and more during your stay.

$$$$

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9.4 / 10

Outstanding(415 Ratings)

Winchester Inn

Hotel

in Ashland

5star

2 guests · 1 bedroom · 1 bath

Business stays, family stays, couples stay, getaway vacation, and rental in Ashland at Winchester Inn for $572 for your next trip.

$$$$

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Frequently asked questions

What are the most popular vacation rental amenities in Ashland?

Non-smoking
Family friendly
No pets allowed

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 $53-$1,196. The average price for rentals in Ashland is $230 per night.

Vacation Rentals in Ashland, OR

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Frequently asked questions

What are the most popular vacation rental amenities in Ashland?

About Ashland

What is the price range for rentals in Ashland?