Ashland Vacation Rentals from ￥15,424: Search Short-Term Rentals

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Our top choices for Ashland vacation rentals

1. East Main Downtown Bungalow

Historic Railroad District

Amy R.

￥34,165 total

includes taxes & fees

Aug 31 - Sep 1

1 bedroom, iron/ironing board, WiFi (free), bed sheets

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

Siskiyou-Hargadine Historic District

Karen G.

￥33,632 total

includes taxes & fees

Sep 7 - Sep 8

3. The Ashland Social | Guest Studio

Ashland

Tara M.

￥35,287 total

includes taxes & fees

Sep 1 - Sep 2

4. Savage Upon Siskiyou

Siskiyou-Hargadine Historic District

megan

￥64,923 total

includes taxes & fees

Aug 26 - Aug 27

Luxury House, 2 Bedrooms, Bathtub, Garden Area | 2 bedrooms, laptop workspace, iron/ironing board, WiFi (free)

5. Barclay Klum House by WanderLodges

Ashland

Melissa

￥43,374 total

includes taxes & fees

Aug 31 - Sep 1

6. Charming carriage house in Ashland near downtown

Skidmore Academy Historic District

Cyndy K.

￥41,117 total

includes taxes & fees

Sep 23 - Sep 24

7. Courtside Cottage - WalkScore 93 - Dog Friendly

Historic Railroad District

Suzanne

￥49,514 total

includes taxes & fees

Sep 1 - Sep 2

8. Quaint Downtown Ashland Studio- pet friendly!

Ashland

Ralph

￥42,087 total

includes taxes & fees

Aug 30 - Aug 31

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

Ashland

Greg M.

￥38,722 total

includes taxes & fees

Sep 23 - Sep 24

Grand House | Living area | 65-inch TV with digital channels, streaming services

10. The Mountain Ave House by WanderLodges

Ashland

Joyce

￥53,700 total

includes taxes & fees

Aug 26 - Aug 27

11. Grandview of Ashland

Ashland

Sonja

￥64,437 total

includes taxes & fees

Sep 6 - Sep 7

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

Ashland

Jeff C.

￥56,744 total

includes taxes & fees

Aug 26 - Aug 27

13. Hanna's House by WanderLodges

Historic Railroad District

David

￥42,367 total

includes taxes & fees

Sep 10 - Sep 11

14. The Ashland Cottage, walk to town

Siskiyou-Hargadine Historic District

Julie S.

￥44,701 total

includes taxes & fees

Aug 30 - Aug 31

15. Chateau Herbe ~ Oberon Suite w/ Kitchen

Ashland

Larry D.

￥37,431 total

includes taxes & fees

Aug 27 - Aug 28

16. A Cowslip's Belle Inn

Ashland

Daniel

￥39,523 total

includes taxes & fees

Aug 27 - Aug 28

2 bedrooms, desk, iron/ironing board, travel crib

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!

Siskiyou-Hargadine Historic District

Denise

￥48,292 total

includes taxes & fees

Aug 26 - Aug 27

18. Affordable Luxury- One block to Downtown

Historic Railroad District

Merlin P.

￥32,994 total

includes taxes & fees

Aug 31 - Sep 1

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

Historic Railroad District

Jim L.

￥48,146 total

includes taxes & fees

Sep 10 - Sep 11

Iron/ironing board, travel crib, WiFi, bed sheets

20. Swank House -Downtown Suite- Pet Friendly

Historic Railroad District

Katie I.

￥31,952 total

includes taxes & fees

Sep 7 - Sep 8

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Top Ashland Hotel Reviews

Plaza Inn & Suites at Ashland Creek

8/10 Good

"Nice place. Friendly staff. Elevators are very slow and not well located."

Comfort Inn & Suites Ashland

10/10 Excellent

"Pleasant and helpful staff. Older well maintained property. Very clean room as well as common areas. The bed was great! Most comfortable nights sleep of my whole road trip. Breakfast was good quality and well monitored by staff. Nothing ran out and the tables and buffet were clean. Our room was huge, more than was expected. Very pleased with this stay all around.:)"

Callahan's Mountain Lodge

10/10 Excellent

"The rooms were updated cabin-style; I was on the ground floor (have a dog) which gave very easy access to beautifully maintained grounds (for people with a spot for dogs too). Staff were uniformly nice, and most had obviously been there for several years. We had a light dinner on the patio with Skeeter Gal, and a lovely breakfast inside with her (rather chilly outside). All-in-all, I loved everything and will definitely return."

Ashland Commons Hostel

8/10 Good

"This was such a fantastic stay! I came for the Oregon Shakespeare Festival, and it was a quick walk to all of the shows and the cute downtown area. As a female solo traveler, I immediately fel t super safe and comfortable here and had zero issues from other guests or management. The only issue I had was how loud the beds were. I stayed in the female only dorm, and the beds were incredibly loud when getting in or out of bed. I'm sure I woke people up every time and vice versa. But as someone who was up and going most of the time, rhis hostel is a FANTASTIC and cute option!"

Find out more about Ashland

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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 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.

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Check prices for these dates

Our top choices for Ashland vacation rentals

1. East Main Downtown Bungalow

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

3. The Ashland Social | Guest Studio

4. Savage Upon Siskiyou

5. Barclay Klum House by WanderLodges

6. Charming carriage house in Ashland near downtown

7. Courtside Cottage - WalkScore 93 - Dog Friendly

8. Quaint Downtown Ashland Studio- pet friendly!

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

10. The Mountain Ave House by WanderLodges

11. Grandview of Ashland

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

13. Hanna's House by WanderLodges

14. The Ashland Cottage, walk to town

15. Chateau Herbe ~ Oberon Suite w/ Kitchen

16. A Cowslip's Belle Inn

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!

18. Affordable Luxury- One block to Downtown

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

20. Swank House -Downtown Suite- Pet Friendly

Find vacation rentals that suit your style

Top Ashland Hotel Reviews

Plaza Inn & Suites at Ashland Creek

Best Western Windsor Inn

Comfort Inn & Suites Ashland

Lithia Springs Resort

Ashland Street Inn

Callahan's Mountain Lodge

Ashland Commons Hostel

Holiday Inn Express & Suites Ashland by IHG

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

Find out more about Ashland

Frequently asked questions

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