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Ashland Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Ashland vacation rentals

A living room with a gray sofa, a brown leather chair, a round ottoman, a coffee table, and a large window with blinds.

1. East Main Downtown Bungalow

East Main Downtown Bungalow
Historic Railroad District
9.4 out of 10, Exceptional, (52 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.
$193 nightly
The price is $215
Aug 31 - Sep 1
Total with taxes and fees
East Main Downtown Bungalow
A bedroom with a bed, bedside tables, a wardrobe, a chair, and a window.

2. 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, (55 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.
$190 nightly
The price is $211
Sep 7 - Sep 8
Total with taxes and fees
Luxuriously comfortable & peaceful getaway downtown Ashland, with views.
A residential property with a gated entrance, a wooden deck, and a well-maintained hedge.

3. 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.
$197 nightly
The price is $220
Sep 1 - Sep 2
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.

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
Aug 26 - Aug 27
Total with taxes and fees
Savage Upon Siskiyou
A bedroom with a large bed, a dresser, a mirror, a chandelier, and a staircase leading to another room.

5. 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
$236 nightly
The price is $263
Aug 30 - Aug 31
Total with taxes and fees
Barclay Klum 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.

6. 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.
$228 nightly
The price is $254
Sep 14 - Sep 15
Total with taxes and fees
Charming carriage house in Ashland near downtown
A modern living room with a grey sofa, a small table, and a basket on a white ottoman.

7. Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (71 reviews)
"Spacious, clean studio to explore Ashland!"
United States
Suzanne
$284 nightly
The price is $317
Sep 1 - Sep 2
Total with taxes and fees
Courtside Cottage - WalkScore 93 - Dog Friendly
A covered outdoor area with a stone pathway, a wooden railing, and a green chair.

8. Quaint Downtown Ashland Studio- pet friendly!

Quaint Downtown Ashland Studio- pet friendly!
Ashland
9.2 out of 10, Wonderful, (16 reviews)
"Excellent communication as I asked if we could check in early as I arrived earlier than expected. Room was quiet and comfortable. Understood the street parking so was expecting it. Centrally located to downtown. No issues. Thanks for the stay."
United States
Ralph
$237 nightly
The price is $265
Aug 30 - Aug 31
Total with taxes and fees
Quaint Downtown Ashland Studio- pet friendly!
A cozy living room with a fireplace, leather sofas, and a dining area with a wooden table and chairs.

9. 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
Aug 26 - Aug 27
Total with taxes and fees
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
A modern kitchen with wooden beams, a dining area with a rug, and a large island.

10. 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
$302 nightly
The price is $337
Aug 26 - Aug 27
Total with taxes and fees
The Mountain Ave House by WanderLodges
A deck with a fire pit, outdoor seating, and a view of the countryside.

11. 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
$399 nightly
The price is $405
Sep 13 - Sep 14
Total with taxes and fees
Grandview of Ashland
A two-story house with a porch, a wooden fence, and a paved driveway.

12. 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
Aug 26 - Aug 27
Total with taxes and fees
Downtown Ashland House - Walk to Plaza and OSF!
A cozy living room with a built-in bench, a flat-screen TV, a bookshelf, and a vase of flowers.

13. 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 10 - Sep 11
Total with taxes and fees
Hanna's House by WanderLodges
A house with a wooden deck, a stone wall, and a wooden fence.

14. 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.
$252 nightly
The price is $281
Aug 30 - Aug 31
Total with taxes and fees
The Ashland Cottage, walk to town
A large, dark-colored building with a symmetrical facade, multiple windows, and a central entrance with a covered walkway.

15. Chateau Herbe ~ Oberon Suite w/ Kitchen

Chateau Herbe ~ Oberon Suite w/ Kitchen
Ashland
9.4 out of 10, Exceptional, (18 reviews)
"very relaxing in a beautiful environment with easy access to the OSF and restaurants "
United States
Larry D.
$232 nightly
The price is $235
Aug 27 - Aug 28
Total with taxes and fees
Chateau Herbe ~ Oberon Suite w/ Kitchen
Two rocking chairs facing a pond with a waterfall, surrounded by lush greenery and wooden fences.

16. 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
$266 nightly
The price is $297
Aug 27 - Aug 28
Total with taxes and fees
A Cowslip's Belle Inn
A hotel room with a bed, a painting of a pelican, a chandelier, and a bathroom visible through an open door.

17. Luxurious 2 BR Red McCall Suite in historic Ashland. Features mountain views, a private deck, shared hot tub access, and a full kitchen. Sleeps 6. Walk to OSF and downtown shops/restaurants!

Luxurious 2 BR Red McCall Suite in historic Ashland. Features mountain views, a private deck, shared hot tub access, and a full kitchen. Sleeps 6. Walk to OSF and downtown shops/restaurants!
Siskiyou-Hargadine Historic District
9.6 out of 10, Exceptional, (13 reviews)
"The place was amazing. Within walking distance to The Cabaret Theater and many wonderful restaurants. "
United States
Denise
$282 nightly
The price is $304
Aug 26 - Aug 27
Total with taxes and fees
Luxurious 2 BR Red McCall Suite in historic Ashland. Features mountain views, a private deck, shared hot tub access, and a full kitchen. Sleeps 6. Walk to OSF and downtown shops/restaurants!
A porch with wicker furniture, a small table, and a plaid rug.

18. Affordable Luxury- One block to Downtown

Affordable Luxury- One block to Downtown
Historic Railroad District
10.0 out of 10, Exceptional, (2 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.
$186 nightly
The price is $207
Aug 31 - Sep 1
Total with taxes and fees
Affordable Luxury- One block to Downtown
A cozy room with a bay window, a television, a bookshelf, and a vase of flowers.

19. 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, (170 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 10 - Sep 11
Total with taxes and fees
Hanna`s House | Downtown Retreat, Steps to OSF
A modern bedroom with a large bed, wooden slatted ceiling, and a flat-screen TV on the wall.

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.
$181 nightly
The price is $201
Sep 7 - Sep 8
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.
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Top Ashland Hotel Reviews

Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

10/10 Excellent
"Staff was great"
Jacob 1-night trip
Posted 1 hour 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 $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 entertainment choices 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?

Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly: This highly rated vacation home rental in Ashland offers a patio, a garden, and a barbecue grill 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. You can relax into your vacation with a selection of games and a hot tub. Some other homes for rent in Ashland include Beautiful bungalow downtown Ashland railroad district, rv parking, adventure! and Gorgeous Lakeside BarnHOUSE + SAUNA!.

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 Thomas 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.