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 / 10.0

Outstanding(186 Ratings)

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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8.4 / 10.0

Outstanding(562 Ratings)

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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8.1 / 10.0

Outstanding(1,290 Ratings)

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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7.8 / 10.0

Outstanding(612 Ratings)

Plaza Inn & Suites at Ashland Creek

Hotel

in Ashland

4-star

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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Explore vacation rentals with the most popular amenities in Ashland

Vacation rentals with air conditioning in Ashland

10.0 / 10.0

Outstanding(134 Ratings)

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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9.9 / 10.0

Outstanding(173 Ratings)

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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8.3 / 10.0

Outstanding(484 Ratings)

Ashland Hills Hotel & Suites

Hotel

in Ashland

3-star

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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7.9 / 10.0

Outstanding(141 Ratings)

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.