A deer on a road with vegetation on the sides.

Ashland Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Ashland vacation rentals

A living room with a TV, sofa, chairs, and a coffee table.

1. Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (10 reviews)
"Great ~ memorable stay. "
United States
Melissa
$229 nightly
The price is $255
Oct 28 - Oct 29
Total with taxes and fees
Barclay Klum House by WanderLodges
A modern bedroom with a bed, bedside tables, a TV, a fireplace, a sofa, and a dining area with stools.

2. Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (77 reviews)
"Excellent stay. Very responsive host. Would come back"
United States
Scott N.
$249 nightly
The price is $277
Oct 27 - Oct 28
Total with taxes and fees
Courtside Cottage - WalkScore 93 - Dog Friendly
A spacious living room with a wooden floor, a sofa, a dining table, and a kitchen area visible through an open doorway.

3. Hanna's House by WanderLodges

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (6 reviews)
"Very cute cottage, 10 min walk to OSF theaters. It has everything you need - full kitchen, front room, and AC for the hot summers! Owner very kind. Will stay there again!"
United States
Robert
$179 nightly
The price is $200
Nov 9 - Nov 10
Total with taxes and fees
Hanna's House by WanderLodges
A two-story house with a gabled roof, a front porch, and a driveway.

4. The Mountain Ave House by WanderLodges

The Mountain Ave House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (8 reviews)
"Lovely space and very comfortable; walkable from downtown "
United States
Joyce
$286 nightly
The price is $319
Nov 1 - Nov 2
Total with taxes and fees
The Mountain Ave House by WanderLodges
A house with a wooden deck, a stone wall, and a wooden fence.

5. The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (241 reviews)
"Beautiful location, comfortable, and nice touches! Loved our stay here."
United States
Julie S.
$258 nightly
The price is $288
Oct 27 - Oct 28
Total with taxes and fees
The Ashland Cottage, walk to town
A covered porch with a ceiling fan, white wicker chairs, a glass table, and a floral painting on the wall.

6. Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Had an amazing stay, thank you!"
United States
megan
$309 nightly
The price is $345
Oct 27 - Oct 28
Total with taxes and fees
Savage Upon Siskiyou
A modern living room with a sofa, a fireplace, a dining table with chairs, and large windows offering a view of the outdoors.

7. Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (11 reviews)
"Stunning views!! A+++ Experience!!"
United States
Jose
$393 nightly
The price is $399
Nov 1 - Nov 2
Total with taxes and fees
Grandview of Ashland
A modern kitchen with white cabinets, a refrigerator, stove, and microwave. There is a dining area with a glass table and brown chairs.

8. Charming carriage house in Ashland near downtown

Charming carriage house in Ashland near downtown
Skidmore Academy Historic District
10.0 out of 10, Exceptional, (13 reviews)
"Lovely stay. "
United States
Cyndy K.
$211 nightly
The price is $235
Oct 29 - Oct 30
Total with taxes and fees
Charming carriage house in Ashland near downtown
A bedroom with a bed, bedside table, and a small table with a chair.

9. The Ashland Social | Guest Studio

The Ashland Social | Guest Studio
Ashland
9.8 out of 10, Exceptional, (29 reviews)
"A great place to call home while you're away from home."
United States
Tara M.
$195 nightly
The price is $217
Oct 27 - Oct 28
Total with taxes and fees
The Ashland Social | Guest Studio
A living room with a gray sofa, a brown leather chair, a round ottoman, a coffee table, and a large window with blinds.

10. East Main Downtown Bungalow

East Main Downtown Bungalow
Historic Railroad District
9.2 out of 10, Wonderful, (55 reviews)
"The bungalow was great. Every room was comfortable and efficient for what we needed. The location is perfect...quiet yet easy walk to anywhere downtown. We would stay here again!!"
United States
Amy R.
$191 nightly
The price is $213
Nov 1 - Nov 2
Total with taxes and fees
East Main Downtown Bungalow
A large, dark-colored building with a symmetrical facade, multiple windows, and a central entrance with a covered walkway.

11. Chateau Herbe ~ Oberon Suite w/ Kitchen

Chateau Herbe ~ Oberon Suite w/ Kitchen
Ashland
9.4 out of 10, Exceptional, (23 reviews)
"Just a little cleaner exterior"
United States
David
$224 nightly
The price is $227
Oct 27 - Oct 28
Total with taxes and fees
Chateau Herbe ~ Oberon Suite w/ Kitchen
A bedroom with a bed, bedside tables, a wardrobe, a chair, and a window.

12. Luxuriously comfortable & peaceful getaway downtown Ashland, with views.

Luxuriously comfortable & peaceful getaway downtown Ashland, with views.
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (61 reviews)
"This is an excellent place to stay. It is well equipped with everything you might need for your stay. And the location is perfect."
United States
Karen G.
$183 nightly
The price is $204
Nov 1 - Nov 2
Total with taxes and fees
Luxuriously comfortable & peaceful getaway downtown Ashland, with views.
A two-story house with a porch, a wooden fence, and a paved driveway.

13. Downtown Ashland Studio - 3 blocks from the plaza!

Downtown Ashland Studio - 3 blocks from the plaza!
Ashland
9.2 out of 10, Wonderful, (24 reviews)
"This was a great little place in a great location. The host was very responsive, really easy to work with and made our stay easy. We highly recommend!"
United States
Santiago L.
$200 nightly
The price is $223
Oct 27 - Oct 28
Total with taxes and fees
Downtown Ashland Studio - 3 blocks from the plaza!
A hotel room with a large bed, two wall-mounted lamps, a chandelier, a window with curtains, and a small table with a chair.

14. The Matriarch| Suite 3 | Pet friendly

The Matriarch| Suite 3 | Pet friendly
Historic Railroad District
9.6 out of 10, Exceptional, (8 reviews)
"We stayed one night and walked easily to a show in one of the Shakespeare theatres. The apartment was super-comfortable and excellent in every way! Highly recommended!"
United States
Daniel
$148 nightly
The price is $165
Oct 28 - Oct 29
Total with taxes and fees
The Matriarch| Suite 3 | Pet friendly
A house with a covered porch, outdoor seating, and a staircase leading to the entrance.

15. Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland

Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
Historic Downtown District
9.8 out of 10, Exceptional, (137 reviews)
"Room was in fantastic shape, clean, well decorated, close to everything. As an Air B&B owner, I recommend, if staying Ashland stay here. Great host."
United States
James C.
$233 nightly
The price is $260
Nov 1 - Nov 2
Total with taxes and fees
Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
A bedroom with a large bed, a red velvet chair, a wooden chest, and a window with patterned curtains.

16. Affordable Luxury- One block to Downtown

Affordable Luxury- One block to Downtown
Historic Railroad District
10.0 out of 10, Exceptional, (3 reviews)
"Perfect location- We typically visit twice a year and like to stay in railroad district as it is close to restaurants and OSF. Highly recommend Swank House."
United States
Sue K.
$143 nightly
The price is $159
Oct 27 - Oct 28
Total with taxes and fees
Affordable Luxury- One block to Downtown
A two-story wooden house with a fenced backyard, outdoor seating, and a statue.

17. The Peerless Hotel | Signature Room #6 | Clawfoot Tub |Historic District

The Peerless Hotel | Signature Room #6 | Clawfoot Tub |Historic District
Historic Railroad District
$158 nightly
The price is $177
Oct 28 - Oct 29
Total with taxes and fees
The Peerless Hotel | Signature Room #6 | Clawfoot Tub |Historic District
A bedroom with a brick wall mural, a bed with red bedding, a wooden dresser, and a nightstand.

18. The Peerless Hotel | Signature ADA Room #1 | Artist`s Abode | Historic District

The Peerless Hotel | Signature ADA Room #1 | Artist`s Abode | Historic District
Historic Railroad District
10.0 out of 10, Exceptional, (1 review)
"The sights stunning, the garden a delight & the jacuzzi soak enriched my soul & ailing body"
United States
David B.
$172 nightly
The price is $191
Oct 27 - Oct 28
Total with taxes and fees
The Peerless Hotel | Signature ADA Room #1 | Artist`s Abode | Historic District
A well-lit bedroom with a large bed, two bedside lamps, a ceiling light fixture, an air conditioning unit, a mirror, and a door.

19. Charming 1 BR Orliena Suite in historic downtown Ashland, OR. Walk to the Oregon Shakespeare Festival, shops, and dining. Features a kitchenette, plush queen bed, and shared hot tub access. Dog friendly!

Charming 1 BR Orliena Suite in historic downtown Ashland, OR. Walk to the Oregon Shakespeare Festival, shops, and dining. Features a kitchenette, plush queen bed, and shared hot tub access. Dog friendly!
Siskiyou-Hargadine Historic District
9.4 out of 10, Exceptional, (10 reviews)
"Perfect location and had all the touches to make it a comfortable stay"
United States
Sara C.
$245 nightly
The price is $264
Oct 27 - Oct 28
Total with taxes and fees
Charming 1 BR Orliena Suite in historic downtown Ashland, OR. Walk to the Oregon Shakespeare Festival, shops, and dining. Features a kitchenette, plush queen bed, and shared hot tub access. Dog friendly!
A modern bedroom with a large bed, wooden panel wall, and bedside tables.

20. Swank House -Downtown Suite- Pet Friendly

Swank House -Downtown Suite- Pet Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (7 reviews)
"Welcoming, cute and private outdoor patio. Cozy but spacious bed and room. Pet-Friendly. Would definitely stay again."
United States
Katie I.
$134 nightly
The price is $149
Oct 27 - Oct 28
Total with taxes and fees
Swank House -Downtown Suite- Pet Friendly
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ashland Hotel Reviews

Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

10/10 Excellent
"This was our second stay at Comfort Inn & Suites in Ashland. We’ve been so impressed with the friendly, professional staff and cleanliness of the hotel in general, we recommended it to some friends!"
Nancy 1-night trip
Posted 7 hours ago
Comfort Inn & Suites Ashland

Find out more about Ashland

Everything you need to know about Ashland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Ashland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ashland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Ashland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ashland. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Ashland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $159 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Ashland rentals

At Expedia, we put the best Ashland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Ashland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ashland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ashland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Ashland?

Yes, we have vacation rentals in Ashland close to ScienceWorks Hands-On Museum, or you can choose a more secluded option if you want a relaxing stay. Visitors to Ashland like the picturesque gardens and acclaimed theater scene this destination is known for. Leave some time to check out the lively festivals and top-notch restaurants during your visit.

What are some of the best vacation rentals that Ashland has to offer?

Premier Downstairs Flat in Perfect Down Town Location : This highly rated vacation home rental in Ashland is located in the city center and offers a balcony, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Some other homes for rent in Ashland include Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly and Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette. .

How many vacation rentals are there in Ashland?

Choose from 106 Expedia vacation rentals in Ashland for a memorable vacation.

What can I see and do in Ashland?

Cultural attractions include Allen Elizabethan Theatre and Angus Bowmer Theatre, whereas Lithia Park and Emigrant Lake are a couple of picturesque spots to enjoy the outdoors. Oregon Shakespeare Festival and Oregon Cabaret Theatre are other places to visit while you're in town.

What are vacation rentals like in Ashland?

Vacation rentals are privately owned properties you can reserve for a short or long stay in Ashland. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for family trips.