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Ashland Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Ashland vacation rentals

A bedroom with a large bed, a dresser, a mirror, a chandelier, and a staircase leading to another room.

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
$238 nightly
The price is $265
Oct 18 - Oct 19
Total with taxes and fees
Barclay Klum House by WanderLodges
A house with a wooden deck, a stone wall, and a wooden fence.

2. The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (240 reviews)
"Beautiful location, comfortable, and nice touches! Loved our stay here."
United States
Julie S.
$258 nightly
The price is $288
Oct 18 - Oct 19
Total with taxes and fees
The Ashland Cottage, walk to town
A deck with a fire pit, outdoor seating, and a view of the countryside.

3. Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (11 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
$416 nightly
The price is $423
Oct 15 - Oct 16
Total with taxes and fees
Grandview of Ashland
A modern living room with a grey sofa, a small table, and a basket on a white ottoman.

4. 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.
$262 nightly
The price is $292
Nov 5 - Nov 6
Total with taxes and fees
Courtside Cottage - WalkScore 93 - Dog Friendly
A cozy living room with a built-in bench, a flat-screen TV, a bookshelf, and a vase of flowers.

5. Hanna's House by WanderLodges

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (5 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
$200 nightly
The price is $223
Oct 18 - Oct 19
Total with taxes and fees
Hanna's House by WanderLodges
A living room with a gray sofa, a brown leather chair, a round ottoman, a coffee table, and a large window with blinds.

6. 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.
$192 nightly
The price is $214
Oct 18 - Oct 19
Total with taxes and fees
East Main Downtown Bungalow
A hotel room with a large bed, two wall-mounted lamps, a chandelier, a window with curtains, and a small table with a chair.

7. 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
$182 nightly
The price is $203
Oct 19 - Oct 20
Total with taxes and fees
The Matriarch| Suite 3 | Pet friendly
A bedroom with a bed, bedside tables, a wardrobe, a chair, and a window.

8. 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, (59 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.
$192 nightly
The price is $214
Nov 1 - Nov 2
Total with taxes and fees
Luxuriously comfortable & peaceful getaway downtown Ashland, with views.
A large, dark-colored building with a symmetrical facade, multiple windows, and a central entrance with a covered walkway.

9. Chateau Herbe ~ Oberon Suite w/ Kitchen

Chateau Herbe ~ Oberon Suite w/ Kitchen
Ashland
9.4 out of 10, Exceptional, (22 reviews)
"Just a little cleaner exterior"
United States
David
$226 nightly
The price is $229
Oct 15 - Oct 16
Total with taxes and fees
Chateau Herbe ~ Oberon Suite w/ Kitchen
A house with a covered porch, outdoor seating, and a staircase leading to the entrance.

10. 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.
$250 nightly
The price is $279
Nov 1 - Nov 2
Total with taxes and fees
Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
A modern kitchen with wooden beams, a dining area with a rug, and a large island.

11. 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
$345 nightly
The price is $385
Oct 18 - Oct 19
Total with taxes and fees
The Mountain Ave House by WanderLodges
A modern kitchen with white cabinets, a refrigerator, stove, and microwave. There is a dining area with a glass table and brown chairs.

12. 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.
$206 nightly
The price is $229
Oct 27 - Oct 28
Total with taxes and fees
Charming carriage house in Ashland near downtown
A residential property with a gated entrance, a wooden deck, and a well-maintained hedge.

13. 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.
$193 nightly
The price is $215
Oct 15 - Oct 16
Total with taxes and fees
The Ashland Social | Guest Studio
A staircase with wooden balusters, a round glass table with chairs, a patterned rug, and a white door with a decorative valance.

14. 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
Oct 25 - Oct 26
Total with taxes and fees
Savage Upon Siskiyou
A porch with wicker furniture, a small table, and a plaid rug.

15. 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.
$151 nightly
The price is $168
Nov 1 - Nov 2
Total with taxes and fees
Affordable Luxury- One block to Downtown
A covered outdoor area with a stone pathway, a wooden railing, and a green chair.

16. Quaint Downtown Ashland Studio- pet friendly!

Quaint Downtown Ashland Studio- pet friendly!
Ashland
9.2 out of 10, Wonderful, (17 reviews)
"Perfect spot to walk to the shows at OSF, walk Lithia Park, and eat and shop at all the downtown spots. Comfortable bed, quiet place, we will try to book this again for our next OSF trip!"
United States
Lara G.
$200 nightly
The price is $223
Oct 18 - Oct 19
Total with taxes and fees
Quaint Downtown Ashland Studio- pet friendly!
A cozy room with a bay window, a television, a bookshelf, and a vase of flowers.

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.
$218 nightly
The price is $244
Oct 18 - Oct 19
Total with taxes and fees
Hanna`s House | Downtown Retreat, Steps to OSF
A living room with a sofa, chairs, a coffee table, a TV, and a chandelier.

18. Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen

Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
Ashland
10.0 out of 10, Exceptional, (6 reviews)
"Lovely stay in a nicely restored historic home. We were very comfortable and the location is great in central Ashland."
United States
Casey K.
$284 nightly
The price is $316
Oct 18 - Oct 19
Total with taxes and fees
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
Terrace/patio

19. 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.
$227 nightly
The price is $245
Oct 18 - Oct 19
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.
A kitchen with a stainless steel sink, white cabinets, and a flat-screen TV mounted above the cabinets.

20. Swank Suites | King with Lux Tub

Swank Suites | King with Lux Tub
Historic Railroad District
9.4 out of 10, Exceptional, (3 reviews)
"This is definitely the place we will hope to stay next time! Great location, sweet cottage, and easy everything."
United States
Bridget A.
$173 nightly
The price is $193
Oct 18 - Oct 19
Total with taxes and fees
Swank Suites | King with Lux Tub
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

Relax Inn At Ashland

Relax Inn At Ashland

8/10 Good
"Great little room that was very clean and had access to a coffee stand, gas station, and several spots for food. The hotel had friendly staff, decent parking, and affordable prices. It was perfect for a stay to visit Ashland, Medford, and Crater Lake. Overall a great stay."
Sean 3-night trip
Posted 4 hours ago
Relax Inn At 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 $168 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.