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
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Ashland vacation rentals

Luxury House, 2 Bedrooms, Bathtub, Garden Area | 2 bedrooms, laptop workspace, iron/ironing board, WiFi (free)

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
$269 nightly
The price is $300
Sep 28 - Sep 29
Total with taxes and fees
Barclay Klum House by WanderLodges
Smart TV

2. East Main Downtown Bungalow

East Main Downtown Bungalow
Historic Railroad District
9.4 out of 10, Exceptional, (53 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.
$183 nightly
The price is $204
Oct 12 - Oct 13
Total with taxes and fees
East Main Downtown Bungalow
Sundeck

3. Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (9 reviews)
"The Grandview house and property far exceeded our expectations. We especially enjoying making meals together in the beautiful kitchen and reminiscing on the deck while taking in the spectacular views. We were fortunate to see lots of wildlife too. We hope to come back next year."
United States
Sonja
$414 nightly
The price is $420
Sep 20 - Sep 21
Total with taxes and fees
Grandview of Ashland
Interior

4. 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
$366 nightly
The price is $408
Sep 20 - Sep 21
Total with taxes and fees
Savage Upon Siskiyou
Exterior detail

5. The Ashland Social | Guest Studio

The Ashland Social | Guest Studio
Ashland
10.0 out of 10, Exceptional, (27 reviews)
"A great place to call home while you're away from home."
United States
Tara M.
$174 nightly
The price is $194
Sep 20 - Sep 21
Total with taxes and fees
The Ashland Social | Guest Studio
1 bedroom, iron/ironing board, WiFi (free), bed sheets

6. 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, (58 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.
$197 nightly
The price is $219
Oct 12 - Oct 13
Total with taxes and fees
Luxuriously comfortable & peaceful getaway downtown Ashland, with views.
Smart TV, books

7. Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (72 reviews)
"Great location in the heart of downtown"
United States
John B.
$259 nightly
The price is $289
Oct 5 - Oct 6
Total with taxes and fees
Courtside Cottage - WalkScore 93 - Dog Friendly
Dining

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.
$210 nightly
The price is $234
Sep 23 - Sep 24
Total with taxes and fees
Charming carriage house in Ashland near downtown
Grand House | Living area | 65-inch TV with digital channels, streaming services

9. The Mountain Ave House by WanderLodges

The Mountain Ave House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (7 reviews)
"Lovely space and very comfortable; walkable from downtown "
United States
Joyce
$357 nightly
The price is $398
Oct 4 - Oct 5
Total with taxes and fees
The Mountain Ave House by WanderLodges
Interior detail

10. Hanna's House by WanderLodges

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (4 reviews)
"Next visit to the OSF no question we’ll stay here if available. Short walking distance to everything in downtown Ashland, yet quiet and private."
United States
David
$308 nightly
The price is $343
Sep 27 - Sep 28
Total with taxes and fees
Hanna's House by WanderLodges
Smart TV, books, music library, stereo

11. Charming well appointed Cottage in Ashland ( 800 + sq. ft. )

Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Ashland
10.0 out of 10, Exceptional, (19 reviews)
"Wonderful location, well appointed place very quiet, beautifully located, and very special place on the farm"
United States
Greg M.
$240 nightly
The price is $244
Sep 23 - Sep 24
Total with taxes and fees
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Rosebud | Terrace/patio

12. A Cowslip's Belle Inn

A Cowslip's Belle Inn
3.0 star property
Ashland
9.6 out of 10, Exceptional, (52 reviews)
"Fantastic location, wonderful amenities. Would absolutely stay here again!!"
United States
Daniel
A Cowslip's Belle Inn
Terrace/patio

13. Quaint Downtown Ashland Studio- pet friendly!

Quaint Downtown Ashland Studio- pet friendly!
Ashland
9.2 out of 10, Wonderful, (16 reviews)
"Very nice private space with a dear walking through the back area."
United States
Jim L.
$235 nightly
The price is $262
Sep 28 - Sep 29
Total with taxes and fees
Quaint Downtown Ashland Studio- pet friendly!
Exterior

14. Chateau Herb ~ Miranda Carriage House Apt

Chateau Herb ~ Miranda Carriage House Apt
Ashland
10.0 out of 10, Exceptional, (11 reviews)
"Loved loved loved staying here and had a fantastic stay with very reasonable rates! It is a bit difficult to find where the apartment was, but once we figured that part out, everything fell right into place. Huge thank you to the hosts for their excellent and timely communication- I also was a huge fan of the easy check in and check out process. Views are spectacular in this area and make for a really special and beautiful stay."
United States
Cameron A.
$258 nightly
The price is $262
Sep 17 - Sep 18
Total with taxes and fees
Chateau Herb ~ Miranda Carriage House Apt
1 bedroom, iron/ironing board, WiFi, bed sheets

15. 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
$185 nightly
The price is $206
Oct 5 - Oct 6
Total with taxes and fees
The Matriarch| Suite 3 | Pet friendly
Terrace/patio

16. Relax in the luxurious 1-bedroom Louisa Suite at RedTail Inn. Enjoy a double rain shower, plush linens, and a shared hot tub. Located near downtown Ashland, with off-street parking and high-speed WiFi.

Relax in the luxurious 1-bedroom Louisa Suite at RedTail Inn. Enjoy a double rain shower, plush linens, and a shared hot tub. Located near downtown Ashland, with off-street parking and high-speed WiFi.
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (12 reviews)
"Close to town, very nice room. We had fun in Ashland."
United States
Adam B.
$228 nightly
The price is $246
Oct 5 - Oct 6
Total with taxes and fees
Relax in the luxurious 1-bedroom Louisa Suite at RedTail Inn. Enjoy a double rain shower, plush linens, and a shared hot tub. Located near downtown Ashland, with off-street parking and high-speed WiFi.
Exterior

17. Chateau Herbe ~ Oberon Suite w/ Kitchen

Chateau Herbe ~ Oberon Suite w/ Kitchen
Ashland
9.4 out of 10, Exceptional, (20 reviews)
"Just a little cleaner exterior"
United States
David
$242 nightly
The price is $246
Sep 27 - Sep 28
Total with taxes and fees
Chateau Herbe ~ Oberon Suite w/ Kitchen
Coffee/tea maker, fridge, microwave, oven

18. Quiet and peaceful cottage close to downtown

Quiet and peaceful cottage close to downtown
Siskiyou-Hargadine Historic District
9.8 out of 10, Exceptional, (70 reviews)
"The property was very pleasant and clean... great directions to get to it, friendly host, sweet outdoor space, clean and welcoming. "
United States
Sue P.
$297 nightly
The price is $331
Sep 19 - Sep 20
Total with taxes and fees
Quiet and peaceful cottage close to downtown
Property grounds

19. Affordable Luxury- One block to Downtown

Affordable Luxury- One block to Downtown
Historic Railroad District
10.0 out of 10, Exceptional, (3 reviews)
"Great place to lay our heads en route to California will be back to try the copper tub another time!"
United States
Merlin P.
$188 nightly
The price is $210
Oct 4 - Oct 5
Total with taxes and fees
Affordable Luxury- One block to Downtown
Iron/ironing board, travel crib, WiFi, bed sheets

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.
$170 nightly
The price is $189
Sep 20 - Sep 21
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

Ashland Springs Hotel

Ashland Springs Hotel

8/10 Good
"Room is quite small actually, not like what you normally expect from the picture on the hotel's webpage."
Qing 1-night trip
Posted 1 hour ago
Ashland Springs Hotel

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 $201 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?

Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette. : This highly rated vacation home rental in Ashland is located in the mountains and has a patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, an oven, and a microwave. Some other homes for rent in Ashland include Beautiful bungalow downtown Ashland railroad district, rv parking, adventure! and Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly.

How many vacation rentals are there in Ashland?

Choose from 108 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.