Ashland Vacation Rentals from SAR 619: Search Short-Term Rentals

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Our top choices for Ashland vacation rentals

A bedroom with a bed, a sofa, a desk, and a window with blinds.

1. Whimsy on B

Historic Railroad District

SAR 623 total

includes taxes & fees

15 Nov - 16 Nov

A wooden door with a small window above it, a porch with a wooden railing, and a green hose on the right side.

2. Whimsy On B 2br & Studio

Historic Railroad District

SAR 1,198 total

includes taxes & fees

16 Nov - 17 Nov

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

3. Barclay Klum House by WanderLodges

Ashland

Melissa

SAR 965 total

includes taxes & fees

12 Nov - 13 Nov

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

Historic Railroad District

Andrea R.

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

Historic Railroad District

Robert

SAR 697 total

includes taxes & fees

17 Nov - 18 Nov

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

6. The Ashland Cottage, walk to town

Siskiyou-Hargadine Historic District

Julie S.

SAR 1,071 total

includes taxes & fees

14 Nov - 15 Nov

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

7. Grandview of Ashland

Ashland

Jose

SAR 1,372 total

includes taxes & fees

2 Dec - 3 Dec

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

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

Siskiyou-Hargadine Historic District

Karen G.

SAR 692 total

includes taxes & fees

16 Nov - 17 Nov

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

9. The Ashland Social | Guest Studio

Ashland

Tara M.

SAR 683 total

includes taxes & fees

12 Nov - 13 Nov

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

10. The Mountain Ave House by WanderLodges

Ashland

Joyce

SAR 1,102 total

includes taxes & fees

17 Nov - 18 Nov

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.

SAR 811 total

includes taxes & fees

23 Nov - 24 Nov

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

12. East Main Downtown Bungalow

Historic Railroad District

Melissa D.

SAR 751 total

includes taxes & fees

23 Nov - 24 Nov

A house with a covered porch, outdoor seating, and a staircase leading to the entrance.

13. Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland

Historic Downtown District

Elaine H.

SAR 988 total

includes taxes & fees

23 Nov - 24 Nov

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

Siskiyou-Hargadine Historic District

megan

SAR 1,323 total

includes taxes & fees

15 Nov - 16 Nov

A covered outdoor area with a stone pathway, a wooden railing, and a green chair.

15. Quaint Downtown Ashland Studio- pet friendly!

Ashland

Lara G.

SAR 774 total

includes taxes & fees

23 Nov - 24 Nov

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

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

Historic Railroad District

Jim L.

SAR 825 total

includes taxes & fees

15 Nov - 16 Nov

A two-story building with a balcony, a patio with white chairs, and a statue.

17. The Peerless Hotel | Signature ADA Room #1 | Artist`s Abode | Historic District

Historic Railroad District

David B.

SAR 689 total

includes taxes & fees

22 Nov - 23 Nov

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

18. Affordable Luxury- One block to Downtown

Historic Railroad District

Sue K.

SAR 619 total

includes taxes & fees

23 Nov - 24 Nov

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

19. Chateau Herbe ~ Oberon Suite w/ Kitchen

Ashland

David

SAR 866 total

includes taxes & fees

15 Nov - 16 Nov

A living room with a green sofa, a television, a wooden coffee table, and a patterned rug.

20. The Matriarch| Suite 3 | Pet friendly

Historic Railroad District

Daniel

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Top Ashland Hotel Reviews

Green Springs Inn

10/10 Excellent

"I stayed here 10 years ago and have always wanted to come back! Very comfortable room in a beautiful setting."

Cedarwood Inn of Ashland

8/10 Good

"The staff was friendly and helpful upon arrival and during our stay. While the properly looks dated on the outside, the room we stayed in was clean, mostly modern, and comfortable. There was a mini fridge, microwave, and coffee maker in the room we did not use but are convenient for longer stays. They offered breakfast (cereal, bagels, English muffins, waffles, yogurt, hardboiled eggs, and fresh fruit) which gave us a good start. The hotel is right alongside a road so you can hear cars driving past and the walls are thin between units. The window screens need replacement to make opening the windows an option during the day (and maybe shield some of the car sounds). Overall, however, it was a pleasant stay and a great value. A good find for a weekend away!"

Timbers INN and Suites

10/10 Excellent

"Place is super cute. Getting in and out is a bit of a pain, tiny parking area, but it was manageable. The water pressure was really good. Oddly, it varied regularly, alternating between a lowish (but usable) flow to something much more forceful. That was my only half-complaint. Even at its lowest, it was still nice and hot and well within normal standards. Room was spacious, bed was nice. I would definitely stay here again."

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.

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Check prices for these dates

Our top choices for Ashland vacation rentals

1. Whimsy on B

2. Whimsy On B 2br & Studio

3. Barclay Klum House by WanderLodges

4. Courtside Cottage - WalkScore 93 - Dog Friendly

5. Hanna's House by WanderLodges

6. The Ashland Cottage, walk to town

7. Grandview of Ashland

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

9. The Ashland Social | Guest Studio

10. The Mountain Ave House by WanderLodges

11. Charming carriage house in Ashland near downtown

12. East Main Downtown Bungalow

13. Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland

14. Savage Upon Siskiyou

15. Quaint Downtown Ashland Studio- pet friendly!

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

17. The Peerless Hotel | Signature ADA Room #1 | Artist`s Abode | Historic District

18. Affordable Luxury- One block to Downtown

19. Chateau Herbe ~ Oberon Suite w/ Kitchen

20. The Matriarch| Suite 3 | Pet friendly

Find vacation rentals that suit your style

Top Ashland Hotel Reviews

Green Springs Inn

Ashland Springs Hotel

Holiday Inn Express & Suites Ashland by IHG

Cedarwood Inn of Ashland

Relax Inn At Ashland

Callahan's Mountain Lodge

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

Baymont by Wyndham

Timbers INN and Suites

Frequently asked questions

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