Ashland Vacation 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
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Ashland vacation rentals

Interior

Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District
The price is P21,197
P33,872 total
includes taxes & fees
Jun 14 - Jun 15
Savage Upon Siskiyou
Sundeck

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 P16,582
P29,277 total
includes taxes & fees
Jun 21 - Jun 22
Grandview of Ashland
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 P13,254
P22,680 total
includes taxes & fees
Jun 7 - Jun 8
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 P22,116
P33,589 total
includes taxes & fees
Jun 30 - Jul 1
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 P9,776
P15,641 total
includes taxes & fees
May 31 - Jun 1
Hanna's 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 P11,990
P16,803 total
includes taxes & fees
Jun 1 - Jun 2
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, (420 reviews)
"Nice place for a weekend getaway. Beautiful lake!"
United States
Athena
The price is P6,043
P6,859 total
includes taxes & fees
May 31 - Jun 1
Rocky Point Resort
Toys

Rosewood Collective- House & Studio

Rosewood Collective- House & Studio
3.0 star property
Medford
The price is P13,254
P30,786 total
includes taxes & fees
Jun 1 - Jun 2
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 P9,927
P24,270 total
includes taxes & fees
Jun 1 - Jun 2
Rosewood Landing- Hot Tub- Sauna
Outdoor dining

Meadowsweet Farm by WanderLodges

Meadowsweet Farm by WanderLodges
3.0 star property
Medford
Meadowsweet Farm by WanderLodges
4 bedrooms

The Eagles Nest in Eagle Point

The Eagles Nest in Eagle Point
2.0 star property
Eagle Point
The price is P16,202
P29,741 total
includes taxes & fees
Jun 1 - Jun 2
The Eagles Nest in Eagle Point
Interior

Riverfront Relaxation: Secluded Jacksonville Home

Riverfront Relaxation: Secluded Jacksonville Home
3.0 star property
Jacksonville
The price is P13,183
P26,575 total
includes taxes & fees
Jun 14 - Jun 15
Riverfront Relaxation: Secluded Jacksonville Home
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 P9,927
P19,417 total
includes taxes & fees
Jun 15 - Jun 16
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 P9,927
P19,417 total
includes taxes & fees
May 31 - Jun 1
Clearview Comfort 3BR Near Airport
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 P8,594
P17,963 total
includes taxes & fees
Jun 1 - Jun 2
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
Lanka Rose House by WanderLodges
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)
"A perfect place to enjoy the winery and countryside! Staff were responsive and friendly!"
United States
Kimberlee
The price is P10,756
P16,770 total
includes taxes & fees
Jun 29 - Jun 30
The Rellik House and Winery
Private kitchenette

Rosewood Studio by WanderLodges

Rosewood Studio by WanderLodges
3.0 star property
Medford
The price is P7,930
P12,041 total
includes taxes & fees
Jun 23 - Jun 24
Rosewood Studio by WanderLodges
2 bedrooms

Ruch Refuge in Jacksonville

Ruch Refuge in Jacksonville
2.0 star property
Jacksonville
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
The price is P7,054
P12,883 total
includes taxes & fees
May 31 - Jun 1
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.
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

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

6/10 Okay
"The mattress are needing to be replaced, which is why you stay at hotels, to sleep. The beds were not comfortable because of the depressions. We asked for a quiet room and the hotel was not close to full and they put us next to a very noisy couple, we had to call the front desk three times to see if they could doing anything. They didn’t, we will never stay there again."
Philip 1-night trip
Posted 2 hours ago
Ashland Hills Hotel & Suites

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 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 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 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 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.