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
24 Apr - 26 Apr
In two months
5 Jun - 7 Jun
In three months
3 Jul - 5 Jul
In four months
31 Jul - 2 Aug

Our top choices for Ashland holiday rentals

Living area

Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (8 reviews)
"Excellent location for in Ashland Easy acces to all local areas and the beds were comfortable! Kitchen stocked with all dishes need to cook meals."
United States
Carmen
The price is S$307
includes taxes & fees
19 Apr - 20 Apr
Barclay Klum House by WanderLodges
Terrace/patio

A Cowslip's Belle Inn

A Cowslip's Belle Inn
3.0 star property
Ashland
9.8 out of 10, Exceptional, (41 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$264
includes taxes & fees
9 Apr - 10 Apr
A Cowslip's Belle Inn
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$508
includes taxes & fees
14 Apr - 15 Apr
The Mountain Ave House by WanderLodges
Sun deck

Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (5 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$620
includes taxes & fees
12 Apr - 13 Apr
Grandview of Ashland
View from property

Rocky Point Resort

Rocky Point Resort
2.5 star property
Klamath Falls
8.2 out of 10, Very good, (409 reviews)
"Had a wonderful stay..!! Would love to stay again."
United States
NAGA HALINI
The price is S$116
includes taxes & fees
13 Apr - 14 Apr
Rocky Point Resort
Flat-screen TV

Rosewood Landing- Hot Tub- Sauna

Rosewood Landing- Hot Tub- Sauna
3.0 star property
Medford
The price is S$595
includes taxes & fees
22 Apr - 23 Apr
Rosewood Landing- Hot Tub- Sauna
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$247
includes taxes & fees
15 Apr - 16 Apr
Medford Home and 2 Condos With Pool and Hot tub
Toys

Rosewood Collective- House & Studio

Rosewood Collective- House & Studio
3.0 star property
Medford
The price is S$788
includes taxes & fees
22 Apr - 23 Apr
Rosewood Collective- House & Studio
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$353
includes taxes & fees
9 Apr - 10 Apr
Clearview Comfort 3BR Near Airport
45-inch Smart TV with digital channels, Netflix, Hulu

Jville Gem- Walk downtown

Jville Gem- Walk downtown
3.0 star property
Jacksonville
The price is S$413
includes taxes & fees
12 Apr - 13 Apr
Jville Gem- Walk downtown
Outdoor dining

Meadowsweet Farm by WanderLodges

Meadowsweet Farm by WanderLodges
3.0 star property
Medford
The price is S$828
includes taxes & fees
22 Apr - 23 Apr
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$316
includes taxes & fees
9 Apr - 10 Apr
Lanka Rose House by WanderLodges
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$344
includes taxes & fees
9 Apr - 10 Apr
Starwood Sanctuary
Living area

Paschal Winery

Paschal Winery
4.5 star property
Talent
9.6 out of 10, Exceptional, (15 reviews)
"The cottage was really nice. It was clean and nicely decorated. It had so many amenities including a well stocked kitchen , comfortable beds and a great hot tub with an amazing view. The management was friendly and allowed us to check in early which was great."
United States
Jennifer
The price is S$327
includes taxes & fees
21 Apr - 22 Apr
Paschal Winery
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$235
includes taxes & fees
22 Apr - 23 Apr
On-site Winery & Tasting Room: Oregon Bungalow!
Living area

The Rellik House and Winery

The Rellik House and Winery
3.5 star property
Central Point
9.4 out of 10, Exceptional, (3 reviews)
"A perfect place to enjoy the winery and countryside! Staff were responsive and friendly!"
United States
Kimberlee
The price is S$333
includes taxes & fees
14 Apr - 15 Apr
The Rellik House and Winery
3 bedrooms

Quail Run River View Cottage

Quail Run River View Cottage
2.0 star property
Jacksonville
The price is S$497
includes taxes & fees
9 Apr - 10 Apr
Quail Run River View Cottage
Private kitchenette

Rosewood Studio by WanderLodges

Rosewood Studio by WanderLodges
3.0 star property
Medford
The price is S$196
includes taxes & fees
22 Apr - 23 Apr
Rosewood Studio by WanderLodges
1 bedroom

Cottage Nine in Jacksonville

Cottage Nine in Jacksonville
2.0 star property
Jacksonville Historic District
The price is S$263
includes taxes & fees
15 Apr - 16 Apr
Cottage Nine in Jacksonville
Room

Luxury Gold Miner Cottage Walk to Britt

Luxury Gold Miner Cottage Walk to Britt
2.0 star property
Jacksonville
The price is S$354
includes taxes & fees
16 Apr - 17 Apr
Luxury Gold Miner Cottage Walk to Britt
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

Stratford Inn

Stratford Inn

10/10 Excellent
"Great stay"
Laurie 1-night trip
Posted 4 hours ago
Stratford Inn

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 renowned opera this destination is known for. Leave some time to check out the lively festivals and top-notch restaurants during your visit.

How many holiday rentals are there in Ashland?

Choose from 102 Expedia holiday rentals in Ashland for a memorable holiday.

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 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.