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Ashland Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Ashland vacation rentals

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

1. Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (10 reviews)
The price is AED 530
AED 1,062 total
includes taxes & fees
27 Sep - 28 Sep
Barclay Klum House by WanderLodges
Smart TV

2. East Main Downtown Bungalow

East Main Downtown Bungalow
Historic Railroad District
9.4 out of 10, Exceptional, (54 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 AED 344
AED 785 total
includes taxes & fees
12 Oct - 13 Oct
East Main Downtown Bungalow
Interior

3. 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 AED 797
AED 1,499 total
includes taxes & fees
28 Sep - 29 Sep
Savage Upon Siskiyou
Sundeck

4. 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
The price is AED 959
AED 1,715 total
includes taxes & fees
6 Oct - 7 Oct
Grandview of Ashland
Property grounds

5. The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (237 reviews)
"Beautiful location, comfortable, and nice touches! Loved our stay here."
United States
Julie S.
The Ashland Cottage, walk to town
Grand House | Living area | 65-inch TV with digital channels, streaming services

6. 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 AED 800
AED 1,425 total
includes taxes & fees
4 Oct - 5 Oct
The Mountain Ave House by WanderLodges
1 bedroom, iron/ironing board, WiFi (free), bed sheets

7. 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, (58 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.
Luxuriously comfortable & peaceful getaway downtown Ashland, with views.
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, (73 reviews)
"Great location in the heart of downtown"
United States
John B.
The price is AED 543
AED 1,031 total
includes taxes & fees
5 Oct - 6 Oct
Courtside Cottage - WalkScore 93 - Dog Friendly
Interior detail

9. 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 AED 834
AED 1,212 total
includes taxes & fees
5 Oct - 6 Oct
Hanna's House by WanderLodges
Dining

10. 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 AED 450
AED 849 total
includes taxes & fees
28 Sep - 29 Sep
Charming carriage house in Ashland near downtown
Exterior detail

11. The Ashland Social | Guest Studio

The Ashland Social | Guest Studio
Ashland
9.8 out of 10, Exceptional, (28 reviews)
"A great place to call home while you're away from home."
United States
Tara M.
The price is AED 294
AED 743 total
includes taxes & fees
5 Oct - 6 Oct
The Ashland Social | Guest Studio
Exterior

12. Chateau Herb ~ Miranda Carriage House Apt

Chateau Herb ~ Miranda Carriage House Apt
Ashland
10.0 out of 10, Exceptional, (11 reviews)
"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."
United States
Cameron A.
The price is AED 731
AED 965 total
includes taxes & fees
27 Sep - 28 Sep
Chateau Herb ~ Miranda Carriage House Apt
Smart TV, books, music library, stereo

13. 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, (19 reviews)
"Wonderful location, well appointed place very quiet, beautifully located, and very special place on the farm"
United States
Greg M.
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Exterior

14. Chateau Herbe ~ Oberon Suite w/ Kitchen

Chateau Herbe ~ Oberon Suite w/ Kitchen
Ashland
9.4 out of 10, Exceptional, (21 reviews)
"Just a little cleaner exterior"
United States
David
The price is AED 602
AED 831 total
includes taxes & fees
27 Sep - 28 Sep
Chateau Herbe ~ Oberon Suite w/ Kitchen
Terrace/patio

15. Quaint Downtown Ashland Studio- pet friendly!

Quaint Downtown Ashland Studio- pet friendly!
Ashland
9.2 out of 10, Wonderful, (16 reviews)
"Perfect spot to walk to the shows at OSF, walk Lithia Park, and eat and shop at all the downtown spots. Comfortable bed, quiet place, we will try to book this again for our next OSF trip!"
United States
Lara G.
Quaint Downtown Ashland Studio- pet friendly!
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)
"Close to town, very nice room. We had fun in Ashland."
United States
Adam B.
The price is AED 485
AED 896 total
includes taxes & fees
5 Oct - 6 Oct
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.
1 bedroom, iron/ironing board, WiFi, bed sheets

17. The Matriarch| Suite 3 | Pet friendly

The Matriarch| Suite 3 | Pet friendly
Historic Railroad District
9.6 out of 10, Exceptional, (8 reviews)
"We stayed one night and walked easily to a show in one of the Shakespeare theatres. The apartment was super-comfortable and excellent in every way! Highly recommended!"
United States
Daniel
The Matriarch| Suite 3 | Pet friendly
Property grounds

18. Affordable Luxury- One block to Downtown

Affordable Luxury- One block to Downtown
Historic Railroad District
10.0 out of 10, Exceptional, (3 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.
Affordable Luxury- One block to Downtown
Coffee/tea maker, fridge, microwave, oven

19. Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
Ashland
9.8 out of 10, Exceptional, (83 reviews)
"Nice spot close to downtown and OSF."
United States
Matthew
The price is AED 645
AED 1,739 total
includes taxes & fees
27 Sep - 28 Sep
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
1 bedroom, iron/ironing board, WiFi, bed sheets

20. Swank Suites- Top Floor + Private Patio

Swank Suites- Top Floor + Private Patio
Historic Railroad District
10.0 out of 10, Exceptional, (4 reviews)
"Nice, quiet and peaceful location. About a 15 minute walk to the theaters that makes you walk through the downtown strip where you won’t want to miss a thing! :)"
United States
Jessica W.
The price is AED 591
AED 745 total
includes taxes & fees
5 Oct - 6 Oct
Swank Suites- Top Floor + Private Patio
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

8/10 Good
"Hot tub very small"
EDWARD 1-night trip
Posted 1 hour ago
Stratford Inn

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 Beautiful bungalow downtown Ashland railroad district, rv parking, adventure!.

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 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.