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(179 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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3.4

Average(372 Reviews)

Motel

in Ashland

Cedarwood Inn of Ashland

Garden · Pool · Kitchen / Kitchenette

Are you ready to indulge in a relaxing getaway? Our Motel in Ashland has everything you need for a rejuvenating stay. Treat yourself to Cedarwood Inn of Ashland's exceptional amenities, such as Air conditioner, Internet / Wifi and Smoking allowed.

$$$$

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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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4.1

Excellent(901 Reviews)

Motel

in Ashland

The Bard's Inn - BW Signature Collection by Best Western

Pool · 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

4.7

Outstanding(133 Reviews)

Apartment

in Ashland

The Maple Apartment at Tudor House Vacation Rentals

6 guests · 2 bedrooms · 2 baths

Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Enjoy the best of Ashland in our Apartment, The Maple Apartment at Tudor House Vacation Rentals. A stunning property with amenities including Air conditioner, Internet / Wifi and Balcony / Patio, and more.

$$$$

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5.0

Outstanding(130 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(90 Reviews)

House

in Ashland

The Perfect Vacation Cottage

4 guests · 2 bedrooms · 2 baths

Garden · Pool · Kitchen / Kitchenette

House in Ashland, for $310 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

$$$$

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5.0

Outstanding(122 Reviews)

House

in Ashland

Stone's Throw Bungalow ~ Walk to Plays, Licensed/Legal, Private Entrance, Garden

2 guests · 1 bedroom · 1 bath

Garden · Pool · Kitchen / Kitchenette

Experience the best of Ashland with this House available for $160. This property is equipped with amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$

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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.