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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sep - 27 Sep

Our top choices for Ashland holiday rentals

Interior

Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District
The price is ฿11,181
฿17,867 total
includes taxes & fees
14 Jun - 15 Jun
Savage Upon Siskiyou
Sun deck

Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (7 reviews)
"The residence was fantastic in every way. Me and my family enjoyed all the amenities and seeing the wildlife around the house outside. This place is a magical place! Thank you again! We will be back in the near future. "
United States
michael
The price is ฿8,747
฿15,443 total
includes taxes & fees
21 Jun - 22 Jun
Grandview of Ashland
Luxury House, 2 Bedrooms, Bathtub, Garden Area | Bathroom | Separate bathtub and shower, deep-soaking bathtub, towels, soap

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 ฿6,992
฿11,963 total
includes taxes & fees
7 Jun - 8 Jun
Barclay Klum House by WanderLodges
Grand House | Living area | 65-inch TV with digital channels, streaming services

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 ฿9,719
฿15,548 total
includes taxes & fees
8 Jun - 9 Jun
The Mountain Ave House by WanderLodges
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 ฿8,492
฿11,969 total
includes taxes & fees
7 Jun - 8 Jun
Hanna's House by WanderLodges
Rosebud | 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 ฿6,326
฿8,866 total
includes taxes & fees
2 Jun - 3 Jun
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, (421 reviews)
"Nice place for a weekend getaway. Beautiful lake!"
United States
Athena
The price is ฿3,189
฿3,619 total
includes taxes & fees
2 Jun - 3 Jun
Rocky Point Resort
Toys

Rosewood Collective- House & Studio

Rosewood Collective- House & Studio
3.0 star property
Medford
The price is ฿6,992
฿16,239 total
includes taxes & fees
2 Jun - 3 Jun
Rosewood Collective- House & Studio
Flat-screen TV

Rosewood Landing- Hot Tub- Sauna

Rosewood Landing- Hot Tub- Sauna
3.0 star property
Medford
The price is ฿5,236
฿12,802 total
includes taxes & fees
2 Jun - 3 Jun
Rosewood Landing- Hot Tub- Sauna
Family Villa, Multiple Bedrooms, Valley View | Outdoor dining

Meadowsweet Farm by WanderLodges

Meadowsweet Farm by WanderLodges
3.0 star property
Medford
The price is ฿10,502
฿20,524 total
includes taxes & fees
2 Jun - 3 Jun
Meadowsweet Farm by WanderLodges
House | 4 bedrooms

The Eagles Nest in Eagle Point

The Eagles Nest in Eagle Point
2.0 star property
Eagle Point
The price is ฿8,549
฿15,692 total
includes taxes & fees
2 Jun - 3 Jun
The Eagles Nest in Eagle Point
House (3 Bedrooms) | Interior

Riverfront Relaxation: Secluded Jacksonville Home

Riverfront Relaxation: Secluded Jacksonville Home
3.0 star property
Jacksonville
The price is ฿6,956
฿14,022 total
includes taxes & fees
14 Jun - 15 Jun
Riverfront Relaxation: Secluded Jacksonville Home
Premium House, 3 Bedrooms, Pets allowed | Living area | Flat-screen TV

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 ฿5,236
฿10,242 total
includes taxes & fees
16 Jun - 17 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 ฿5,236
฿10,242 total
includes taxes & fees
2 Jun - 3 Jun
Clearview Comfort 3BR Near Airport
Glamp Cottage Trailer | Living area | Flat-screen TV, fireplace

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 ฿4,534
฿9,478 total
includes taxes & fees
2 Jun - 3 Jun
Paschal Winery
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 ฿9,654
฿15,578 total
includes taxes & fees
30 Jun - 1 Jul
Lanka Rose House by WanderLodges
Deluxe Suite | Bathroom | Hair dryer, towels, toilet paper

The Rellik House and Winery

The Rellik House and Winery
3.5 star property
Central Point
9.6 out of 10, Exceptional, (4 reviews)
"A perfect place to enjoy the winery and countryside! Staff were responsive and friendly!"
United States
Kimberlee
The price is ฿5,675
฿8,848 total
includes taxes & fees
2 Jul - 3 Jul
The Rellik House and Winery
Studio, 1 Queen Bed, Kitchenette | Private kitchenette | Coffee/tea maker, electric kettle, toaster, paper towels

Rosewood Studio by WanderLodges

Rosewood Studio by WanderLodges
3.0 star property
Medford
The price is ฿4,183
฿6,352 total
includes taxes & fees
23 Jun - 24 Jun
Rosewood Studio by WanderLodges
House | 2 bedrooms

Ruch Refuge in Jacksonville

Ruch Refuge in Jacksonville
2.0 star property
Jacksonville
The price is ฿6,856
฿11,668 total
includes taxes & fees
3 Jun - 4 Jun
Ruch Refuge in Jacksonville
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
Medford Home and 2 Condos With Pool and Hot tub
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

Prospero's Flagship Inn

Prospero's Flagship Inn

6/10 Okay
"Breakfast did not include any protein (egg, bacon, sausage, etc.) but lots of carbs."
Edward 1-night trip
Posted 2 hours ago
Prospero's Flagship 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:

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

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 107 Expedia holiday rentals in Ashland for a memorable holiday.

What can I see and do in Ashland?

Cultural attractions include Allen Elizabethan Theatre and Oregon Shakespeare Festival, whereas Lithia Park and Howard Prairie Lake are a couple of picturesque spots to enjoy the outdoors. Oregon Cabaret Theatre and Mount Ashland Ski Area 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.