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Ashland Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Ashland vacation rentals

Luxury House, 2 Bedrooms, Bathtub, Garden Area

1. Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (9 reviews)
"Great ~ memorable stay. "
United States
Melissa
$250 nightly
The price is $279
Sep 7 - Sep 8
Total with taxes and fees
Barclay Klum House by WanderLodges
Living area

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.
$202 nightly
The price is $226
Sep 9 - Sep 10
Total with taxes and fees
East Main Downtown Bungalow
Interior detail

3. 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
$248 nightly
The price is $277
Sep 20 - Sep 21
Total with taxes and fees
Hanna's House by WanderLodges
Grand House | Living area

4. 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
$307 nightly
The price is $343
Sep 7 - Sep 8
Total with taxes and fees
The Mountain Ave House by WanderLodges
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.
$183 nightly
The price is $204
Sep 14 - Sep 15
Total with taxes and fees
The Ashland Social | Guest Studio
Sundeck

6. 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
$426 nightly
The price is $432
Sep 13 - Sep 14
Total with taxes and fees
Grandview of Ashland
Interior

7. 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
$378 nightly
The price is $421
Sep 13 - Sep 14
Total with taxes and fees
Savage Upon Siskiyou
Property grounds

8. The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (233 reviews)
"Beautiful location, comfortable, and nice touches! Loved our stay here."
United States
Julie S.
$251 nightly
The price is $280
Sep 7 - Sep 8
Total with taxes and fees
The Ashland Cottage, walk to town
Living area

9. 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.
$343 nightly
The price is $382
Sep 28 - Sep 29
Total with taxes and fees
Courtside Cottage - WalkScore 93 - Dog Friendly
Terrace/patio

10. 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.
$236 nightly
The price is $263
Sep 7 - Sep 8
Total with taxes and fees
Quaint Downtown Ashland Studio- pet friendly!
Room

11. 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, (57 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.
$206 nightly
The price is $229
Oct 5 - Oct 6
Total with taxes and fees
Luxuriously comfortable & peaceful getaway downtown Ashland, with views.
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
$273 nightly
The price is $304
Sep 7 - Sep 8
Total with taxes and fees
A Cowslip's Belle Inn
Dining

13. 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.
$215 nightly
The price is $240
Sep 14 - Sep 15
Total with taxes and fees
Charming carriage house in Ashland near downtown
Living area

14. 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, (18 reviews)
"Wonderful location, well appointed place very quiet, beautifully located, and very special place on the farm"
United States
Greg M.
$241 nightly
The price is $245
Sep 7 - Sep 8
Total with taxes and fees
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Exterior

15. Chateau Herbe ~ Oberon Suite w/ Kitchen

Chateau Herbe ~ Oberon Suite w/ Kitchen
Ashland
9.4 out of 10, Exceptional, (19 reviews)
"Just a little cleaner exterior"
United States
David
$223 nightly
The price is $226
Sep 7 - Sep 8
Total with taxes and fees
Chateau Herbe ~ Oberon Suite w/ Kitchen
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.
$226 nightly
The price is $244
Oct 6 - Oct 7
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.
Living area

17. Hanna`s House | Downtown Retreat, Steps to OSF

Hanna`s House | Downtown Retreat, Steps to OSF
Historic Railroad District
10.0 out of 10, Exceptional, (171 reviews)
"Excellent quaint cottage….great location….easy check in….very well stocked and very comfortable….second year at this cottage and will be back next year!!"
United States
Jim L.
$272 nightly
The price is $303
Sep 20 - Sep 21
Total with taxes and fees
Hanna`s House | Downtown Retreat, Steps to OSF
Room

18. The Matriarch| Suite 3 | Pet friendly

The Matriarch| Suite 3 | Pet friendly
Historic Railroad District
9.6 out of 10, Exceptional, (7 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
$182 nightly
The price is $203
Oct 5 - Oct 6
Total with taxes and fees
The Matriarch| Suite 3 | Pet friendly
Private kitchen

19. Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
Ashland
9.8 out of 10, Exceptional, (76 reviews)
"Nice spot close to downtown and OSF."
United States
Matthew
$430 nightly
The price is $479
Sep 7 - Sep 8
Total with taxes and fees
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
Exterior

20. Downtown Ashland House - Walk to Plaza and OSF!

Downtown Ashland House - Walk to Plaza and OSF!
Ashland
9.8 out of 10, Exceptional, (46 reviews)
"Great place to stay and so close to shops and restaurants. "
United States
Jeff C.
$320 nightly
The price is $357
Sep 7 - Sep 8
Total with taxes and fees
Downtown Ashland House - Walk to Plaza and OSF!
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.
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Top Ashland Hotel Reviews

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

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

8/10 Good
"Great location for Shakespeare theaters."
DENNIS 1-night trip
Posted 1 hour ago
The Bard's Inn, BW Signature Collection by Best Western

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 $97 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?

Beautiful bungalow downtown Ashland railroad district, rv parking, adventure!: This highly rated vacation home rental in Ashland has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Some other homes for rent in Ashland include Gorgeous Lakeside BarnHOUSE + SAUNA! and Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly.

How many vacation rentals are there in Ashland?

Choose from 107 Expedia vacation rentals in Ashland for a memorable vacation.

What can I see and do in Ashland?

Cultural attractions include Allen Elizabethan Theatre and Oregon Shakespeare Festival, whereas Lithia Park and Emigrant Lake are a couple of picturesque spots to enjoy the outdoors. Oregon Cabaret Theatre and Mount Ashland Ski Area 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.