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Ashland Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Ashland vacation rentals

Smart TV

1. East Main Downtown Bungalow

East Main Downtown Bungalow
Historic Railroad District
9.4 out of 10, Exceptional, (51 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.
The price is ￥15,151
￥34,490 total
includes taxes & fees
Aug 31 - Sep 1
East Main Downtown Bungalow
1 bedroom, iron/ironing board, WiFi (free), bed sheets

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, (54 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.
The price is ￥18,429
￥33,701 total
includes taxes & fees
Sep 7 - Sep 8
Luxuriously comfortable & peaceful getaway downtown Ashland, with views.
Exterior detail

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.
The price is ￥16,899
￥38,124 total
includes taxes & fees
Sep 1 - Sep 2
The Ashland Social | Guest Studio
Interior

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
The price is ￥36,507
￥67,191 total
includes taxes & fees
Sep 13 - Sep 14
Savage Upon Siskiyou
Luxury House, 2 Bedrooms, Bathtub, Garden Area | 2 bedrooms, laptop workspace, iron/ironing board, WiFi (free)

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
The price is ￥24,912
￥48,218 total
includes taxes & fees
Aug 24 - Aug 25
Barclay Klum House by WanderLodges
Smart TV, books, music library, stereo

6. 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.
The price is ￥21,522
￥38,998 total
includes taxes & fees
Aug 22 - Aug 23
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Dining

7. 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.
The price is ￥19,800
￥37,542 total
includes taxes & fees
Aug 25 - Aug 26
Charming carriage house in Ashland near downtown
Smart TV, books

8. 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
The price is ￥24,948
￥47,015 total
includes taxes & fees
Aug 19 - Aug 20
Courtside Cottage - WalkScore 93 - Dog Friendly
Terrace/patio

9. 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
The price is ￥19,928
￥42,175 total
includes taxes & fees
Aug 23 - Aug 24
Quaint Downtown Ashland Studio- pet friendly!
Interior detail

10. 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
The price is ￥26,160
￥41,433 total
includes taxes & fees
Sep 7 - Sep 8
Hanna's House by WanderLodges
Rosebud | Terrace/patio

11. A Cowslip's Belle Inn

A Cowslip's Belle Inn
3.0 star property
Ashland
9.6 out of 10, Exceptional, (50 reviews)
"Fantastic location, wonderful amenities. Would absolutely stay here again!!"
United States
Daniel
The price is ￥27,581
￥39,640 total
includes taxes & fees
Aug 19 - Aug 20
A Cowslip's Belle Inn
Exterior

12. 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.
The price is ￥26,097
￥37,485 total
includes taxes & fees
Aug 20 - Aug 21
Chateau Herbe ~ Oberon Suite w/ Kitchen
Sundeck

13. Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (8 reviews)
"Grandview of Ashland was a beautiful home!! It was super clean and the views of the valley were amazing. Our entire party had a wonderful time and would 100% stay there again. Highly recommend!"
United States
Paul
The price is ￥38,273
￥71,048 total
includes taxes & fees
Aug 26 - Aug 27
Grandview of Ashland
Grand House | Living area | 65-inch TV with digital channels, streaming services

14. 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
The price is ￥36,935
￥64,276 total
includes taxes & fees
Aug 31 - Sep 1
The Mountain Ave House by WanderLodges
Property grounds

15. The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (232 reviews)
"Beautiful location, comfortable, and nice touches! Loved our stay here."
United States
Julie S.
The price is ￥26,623
￥46,217 total
includes taxes & fees
Aug 24 - Aug 25
The Ashland Cottage, walk to town
Terrace/patio

16. 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)
"Well stocked and comfortable, we didn’t have time for the hot tub, but the shower was lovely."
United States
ashley b.
The price is ￥23,834
￥42,871 total
includes taxes & fees
Aug 23 - Aug 24
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.
Smart TV

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, (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.
The price is ￥26,129
￥48,288 total
includes taxes & fees
Sep 7 - Sep 8
Hanna`s House | Downtown Retreat, Steps to OSF
Property grounds

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.
The price is ￥25,826
￥32,885 total
includes taxes & fees
Aug 23 - Aug 24
Affordable Luxury- One block to Downtown
Iron/ironing board, travel crib, WiFi, bed sheets

19. 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.
The price is ￥26,464
￥34,746 total
includes taxes & fees
Sep 7 - Sep 8
Swank House -Downtown Suite- Pet Friendly
Exterior

20. 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.
Downtown Ashland House - Walk to Plaza and OSF!
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

Stratford Inn

Stratford Inn

10/10 Excellent
"Staff was great and housekeeping very accommodating. Nice to have a great room and breakfast."
Diane 4-night trip
Posted 13 hours ago
Stratford Inn

Find out more about Ashland

Search for holiday rentals in Ashland on Expedia! You can easily find your home rentals, villas, holiday apartments in Ashland using one of the methods below:

  • View our selection of featured holiday rentals in Ashland
  • Use the map to find apartments and other holiday homes in the Ashland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Ashland while they last

Look no further and take a look at our great range of rental properties in Ashland!

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 The R&R is a large 5-bedroom house in beautiful Ashland…amazing sunset views, and Beautiful bungalow downtown Ashland railroad district, rv parking, adventure!.

How many vacation rentals are there in Ashland?

Choose from 107 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.