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

5.0

Outstanding(173 Reviews)

Cottage

in Ashland

The Ashland Cottage, walk to town

4 guests · 1 bedroom · 2 baths

Garden · Kitchen / 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(574 Reviews)

Motel

in Ashland

Flagship Inn of Ashland

Garden · Pool · Kitchen / Kitchenette

Motel in Ashland, for $111 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

$$$$

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4.1

Excellent(501 Reviews)

Hotel

in Ashland

3star

Best Western Windsor Inn

Garden · Pool · Pets allowed

When traveling to Ashland, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $92 per night.

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3.9

Good(702 Reviews)

Hotel

in Ashland

4star

Plaza Inn & Suites at Ashland Creek

Garden · Pets allowed · Kitchen / 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

5.0

Outstanding(126 Reviews)

House

in Ashland

Railroad District, steps to downtown, everything you need to enjoy Ashland!

5 guests · 2 bedrooms · 2 baths

Kitchen / Kitchenette · Air conditioner · Internet / Wifi

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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5.0

Outstanding(156 Reviews)

House

in Ashland

In the historic railroad district, walking distance to all the best of Ashland!

8 guests · 4 bedrooms · 3 baths

Garden · Kitchen / 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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4.2

Excellent(1,387 Reviews)

Motel

in Ashland

Timbers INN and Suites

Pool · Pets allowed · Kitchen / 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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4.8

Outstanding(42 Reviews)

House

in Ashland

Second Street Cottages

Kitchen / Kitchenette · Air conditioner · Internet / Wifi

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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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 / 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.