Ashland Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sept - 13 Sept

Our top choices for Ashland holiday rentals

Sun deck

Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (7 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 S$710
includes taxes & fees
7 Jun - 8 Jun
Grandview of Ashland
Interior

Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District
The price is S$539
includes taxes & fees
25 May - 26 May
Savage Upon Siskiyou
Interior detail

Hanna's House by WanderLodges

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (3 reviews)
"Thoughtfully arranged and provisioned. A hidden gem."
United States
Jerald
The price is S$247
includes taxes & fees
25 May - 26 May
Hanna's House by WanderLodges
2 bedrooms, laptop workspace, iron/ironing board, free WiFi

Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (8 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is S$347
includes taxes & fees
25 May - 26 May
Barclay Klum House by WanderLodges
Living area

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 S$657
includes taxes & fees
15 Jun - 16 Jun
The Mountain Ave House by WanderLodges
Terrace/patio

A Cowslip's Belle Inn

A Cowslip's Belle Inn
3.0 star property
Ashland
9.6 out of 10, Exceptional, (43 reviews)
"Cowslip’s Belle Inn was like walking through a Lord of the Rings scene with all the vibrant colors and even a koi pond. The hosts were amazing! They guided me into the town, welcomed me to their area and gave recommendations for nearby wineries. I’ll be back for an extended stay. "
United States
SHAWNDA
The price is S$305
includes taxes & fees
25 May - 26 May
A Cowslip's Belle Inn
View from property

Rocky Point Resort

Rocky Point Resort
2.5 star property
Klamath Falls
8.2 out of 10, Very good, (418 reviews)
"Good for the price"
United States
Randal
The price is S$143
includes taxes & fees
25 May - 26 May
Rocky Point Resort
Living area

Starwood Sanctuary

Starwood Sanctuary
3.0 star property
Medford
10.0 out of 10, Exceptional, (1 review)
"It really was a sanctuary! I had car troubles on a trip and this was a lovely home away from home. It had everything I needed and then some. I don't even have a dog but I think it's awesome that you have a pet door to the backyard!"
United States
Nathan
The price is S$429
includes taxes & fees
1 Jun - 2 Jun
Starwood Sanctuary
Dining

Clearview Comfort 3BR Near Airport

Clearview Comfort 3BR Near Airport
3.0 star property
Medford
10.0 out of 10, Exceptional, (3 reviews)
"The house is clean. There is 1 driveway parking, however street parking is available. Location is good, there are many dining and grocery options nearby."
United States
Phuc
The price is S$358
includes taxes & fees
26 May - 27 May
Clearview Comfort 3BR Near Airport
Flat-screen TV

Rosewood Landing- Hot Tub- Sauna

Rosewood Landing- Hot Tub- Sauna
3.0 star property
Medford
The price is S$530
includes taxes & fees
1 Jun - 2 Jun
Rosewood Landing- Hot Tub- Sauna
Interior

On-site Winery & Tasting Room: Oregon Bungalow!

On-site Winery & Tasting Room: Oregon Bungalow!
3.0 star property
Central Point
8.4 out of 10, Very good, (5 reviews)
"Loved our stay at the Bungalow. The owners were so welcoming, helpful and friendly. The bungalow was very clean and had well equipped. It wa a great location for everything we wanted to do. The bungalow was even nicer than the pictures. We would definitely recommend this stay! "
United States
Deborah
The price is S$298
includes taxes & fees
26 May - 27 May
On-site Winery & Tasting Room: Oregon Bungalow!
Living area

Paschal Winery

Paschal Winery
4.5 star property
Talent
9.8 out of 10, Exceptional, (18 reviews)
"Incredible experience, fabulous wine, wish we had stayed longer to soak in the beauty of the experience. "
United States
Frankie
The price is S$359
includes taxes & fees
26 May - 27 May
Paschal Winery
Living area

Jville Gem- Walk downtown

Jville Gem- Walk downtown
3.0 star property
Jacksonville
The price is S$483
includes taxes & fees
25 May - 26 May
Jville Gem- Walk downtown
Exterior

Medford Home and 2 Condos With Pool and Hot tub

Medford Home and 2 Condos With Pool and Hot tub
2.0 star property
Medford
The price is S$287
includes taxes & fees
26 May - 27 May
Medford Home and 2 Condos With Pool and Hot tub
Living area

The Rellik House and Winery

The Rellik House and Winery
3.5 star property
Central Point
9.6 out of 10, Exceptional, (4 reviews)
"It’s located on a winery. Pet friendly. Clean .heated pool. It’s located on a winery . Cute little walking path with a pond and alpacas on site. Did I mention it’s on a winery. Very quiet and peaceful when the winery closed. We had the whole property to our self. Will definitely return "
United States
Renee
The price is S$348
includes taxes & fees
22 Jun - 23 Jun
The Rellik House and Winery
Toys

Rosewood Collective- House & Studio

Rosewood Collective- House & Studio
3.0 star property
Medford
The price is S$847
includes taxes & fees
4 Jun - 5 Jun
Rosewood Collective- House & Studio
Outdoor dining

Meadowsweet Farm by WanderLodges

Meadowsweet Farm by WanderLodges
3.0 star property
Medford
The price is S$699
includes taxes & fees
25 May - 26 May
Meadowsweet Farm by WanderLodges
35-inch Smart TV with digital channels, Netflix, Hulu

Lanka Rose House by WanderLodges

Lanka Rose House by WanderLodges
3.5 star property
Phoenix
10.0 out of 10, Exceptional, (2 reviews)
"Very cute house with all the necessities for a cozy stay. "
United States
Roxanne
The price is S$896
includes taxes & fees
23 Jun - 24 Jun
Lanka Rose House by WanderLodges
Private kitchenette

Rosewood Studio by WanderLodges

Rosewood Studio by WanderLodges
3.0 star property
Medford
The price is S$229
includes taxes & fees
25 May - 26 May
Rosewood Studio by WanderLodges
Interior

Riverfront Relaxation: Secluded Jacksonville Home

Riverfront Relaxation: Secluded Jacksonville Home
3.0 star property
Jacksonville
Riverfront Relaxation: Secluded Jacksonville Home
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ashland Hotel Reviews

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

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

10/10 Excellent
"The stay was very nice with the exception of one member of our group who used a wheelchair had to go through the kitchen to enter the restaurant. That problem could be easily be avoided by putting another gate in front of the restaurant door in the looks area. Thank you."
Margaret 2-night trip
Posted 1 hour ago
The Bard's Inn, BW Signature Collection by Best Western

Frequently asked questions

Can I find holiday rentals in Ashland?

Yes, there are holiday rentals in Ashland close to ScienceWorks Hands-On Museum, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Ashland like the picturesque gardens and lively festivals this destination is known for. Leave some time to check out the renowned opera and top-notch restaurants during your visit.

How many holiday rentals are there in Ashland?

Choose from 105 Expedia holiday rentals in Ashland for a memorable holiday.

What can I see and do in Ashland?

Cultural attractions include Allen Elizabethan Theatre and Angus Bowmer Theatre, whereas Lithia Park and Howard Prairie 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 holiday rentals like in Ashland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Ashland. Holiday rentals feature extras like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a family getaway.