Ashland Vacation Rentals from $244: Search Short-Term Rentals

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Our top choices for Ashland vacation rentals

A deck with a fire pit, outdoor seating, and a view of the countryside.

1. Grandview of Ashland

Ashland

Sonja

$426 nightly

Oct 14 - Oct 15

Total with taxes and fees

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

2. Barclay Klum House by WanderLodges

Ashland

Melissa

$250 nightly

Oct 4 - Oct 5

Total with taxes and fees

A cozy living room with a built-in bench, a flat-screen TV, a bookshelf, and a vase of flowers.

3. Hanna's House by WanderLodges

Historic Railroad District

David

$198 nightly

Oct 5 - Oct 6

Total with taxes and fees

A house with a wooden deck, a stone wall, and a wooden fence.

4. The Ashland Cottage, walk to town

Siskiyou-Hargadine Historic District

Julie S.

$258 nightly

Oct 18 - Oct 19

Total with taxes and fees

A modern kitchen with wooden beams, a dining area with a rug, and a large island.

5. The Mountain Ave House by WanderLodges

Ashland

Joyce

$345 nightly

Oct 7 - Oct 8

Total with taxes and fees

A bedroom with a bed, bedside tables, a wardrobe, a chair, and a window.

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

Siskiyou-Hargadine Historic District

Karen G.

$206 nightly

Oct 25 - Oct 26

Total with taxes and fees

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

7. East Main Downtown Bungalow

Historic Railroad District

Amy R.

$192 nightly

Oct 12 - Oct 13

Total with taxes and fees

A large, dark-colored building with a symmetrical facade, multiple windows, and a central entrance with a covered walkway.

8. Chateau Herbe ~ Oberon Suite w/ Kitchen

Ashland

David

$227 nightly

Oct 4 - Oct 5

Total with taxes and fees

A modern living room with a grey sofa, a small table, and a basket on a white ottoman.

9. Courtside Cottage - WalkScore 93 - Dog Friendly

Historic Railroad District

John B.

$230 nightly

Oct 5 - Oct 6

Total with taxes and fees

A staircase with wooden balusters, a round glass table with chairs, a patterned rug, and a white door with a decorative valance.

10. Savage Upon Siskiyou

Siskiyou-Hargadine Historic District

megan

$378 nightly

Oct 6 - Oct 7

Total with taxes and fees

A modern kitchen with white cabinets, a refrigerator, stove, and microwave. There is a dining area with a glass table and brown chairs.

11. Charming carriage house in Ashland near downtown

Skidmore Academy Historic District

Cyndy K.

$206 nightly

Oct 5 - Oct 6

Total with taxes and fees

A cozy living room with a fireplace, leather sofas, and a dining area with a wooden table and chairs.

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

Ashland

Greg M.

$240 nightly

Oct 4 - Oct 5

Total with taxes and fees

A cozy room with a bay window, a television, a bookshelf, and a vase of flowers.

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

Historic Railroad District

Jim L.

$239 nightly

Oct 4 - Oct 5

Total with taxes and fees

A two-story house with a porch, a wooden fence, and a paved driveway.

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

Ashland

Santiago L.

$226 nightly

Oct 5 - Oct 6

Total with taxes and fees

A porch with wicker furniture, a small table, and a plaid rug.

15. Affordable Luxury- One block to Downtown

Historic Railroad District

Sue K.

$151 nightly

Nov 1 - Nov 2

Total with taxes and fees

A residential property with a gated entrance, a wooden deck, and a well-maintained hedge.

16. The Ashland Social | Guest Studio

Ashland

Tara M.

$181 nightly

Oct 5 - Oct 6

Total with taxes and fees

A hotel room with a large bed, two wall-mounted lamps, a chandelier, a window with curtains, and a small table with a chair.

17. The Matriarch| Suite 3 | Pet friendly

Historic Railroad District

Daniel

$185 nightly

Oct 19 - Oct 20

Total with taxes and fees

18. 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

Adam B.

$226 nightly

Nov 1 - Nov 2

Total with taxes and fees

19. Chateau Herb ~ Miranda Carriage House Apt

Ashland

"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."

Cameron A.

$248 nightly

Oct 4 - Oct 5

Total with taxes and fees

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

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

Ashland

Casey K.

$299 nightly

Oct 4 - Oct 5

Total with taxes and fees

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Top Ashland Hotel Reviews

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

10/10 Excellent

"Close to theater and town great breakfast"

Callahan's Mountain Lodge

10/10 Excellent

"The new smaller portion menu is a plus and minus. Less food, same price. No add one is a big minus. I miss Shawn, the bartender, he gave it a step up..I miss the breakfast included, the new management does not do any bonues to people staying over night. We were on a time crunch and could not do a full service breakfast plus costs. The al a catre or grab and go way one of our reasons for using Callahans as our stop over. Our room was okish. I don't like the soap/shampoo/conditioner dispensers. Since 2 of the 3 were missing. Our room had a broken lock, so I could not get into my room with the key card. The new management needs to upgrade the locks on all doors, take care of guests and make sure all of the amenities are available. We talked to staff, they are happy with the new management, they are taken care of, in return, the guests are suffering. We've stayed her many times. We see good and bad with the new management. Usually I would give a 5 star review, I think with our current experience, it's maybe a 3+ish. We drive to pnw 3-5 times a year. Next time we might power through to a better location with better amenities, for the same price. I'm sad to leave this honest review, because we have always loved Callahans. We've referred Callahans. This last trip was sub par. All of the staff are wonderful, I fully think this is a management issue. Not a staff issue. On a positive side note, Sunshine, the server is a ray of sunshine. Thank you"

Lithia Springs Resort

10/10 Excellent

"Excellent stay at a beautiful property! The room was large and included a soaking tub with their famous mineral water, a sitting room, and a kitchenette. The property offers complimentary bicycles and laundry services, as well as afternoon tea with cookies from 3-5. I would definitely stay here again!"

Ashland Motel - Oregon

8/10 Good

"The room itself was cute and clean. The outside and the AC unit were a little dated but worked well. I did really miss having an ice machine but it was clearly stated that was not an offered amenity so it was not a surprise. The staff was wonderful and the description was informative and accurate. A great overall experience."

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 $244 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.

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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.

Ashland Vacation Rentals

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Check prices for these dates

Our top choices for Ashland vacation rentals

1. Grandview of Ashland

2. Barclay Klum House by WanderLodges

3. Hanna's House by WanderLodges

4. The Ashland Cottage, walk to town

5. The Mountain Ave House by WanderLodges

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

7. East Main Downtown Bungalow

8. Chateau Herbe ~ Oberon Suite w/ Kitchen

9. Courtside Cottage - WalkScore 93 - Dog Friendly

10. Savage Upon Siskiyou

11. Charming carriage house in Ashland near downtown

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

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

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

15. Affordable Luxury- One block to Downtown

16. The Ashland Social | Guest Studio

17. The Matriarch| Suite 3 | Pet friendly

18. 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.

19. Chateau Herb ~ Miranda Carriage House Apt

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

Find vacation rentals that suit your style

Top Ashland Hotel Reviews

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

Find out more about Ashland

Explore a world of travel with Expedia

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