Ashland Vacation Rentals

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Check prices for these dates

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

Our top choices for Ashland vacation rentals

Sundeck

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 P18,031
P29,258 total
includes taxes & fees
Apr 12 - Apr 13
Grandview of Ashland
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 P6,429
P15,132 total
includes taxes & fees
Apr 19 - Apr 20
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 P14,413
P25,416 total
includes taxes & fees
Apr 12 - Apr 13
The Mountain Ave 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 P8,141
P12,439 total
includes taxes & fees
Apr 9 - Apr 10
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, (409 reviews)
"Had a wonderful stay..!! Would love to stay again."
United States
NAGA HALINI
The price is P4,808
P5,457 total
includes taxes & fees
Apr 13 - Apr 14
Rocky Point Resort
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 P6,260
P11,664 total
includes taxes & fees
Apr 11 - Apr 12
Medford Home and 2 Condos With Pool and Hot tub
Flat-screen TV

Rosewood Landing- Hot Tub- Sauna

Rosewood Landing- Hot Tub- Sauna
3.0 star property
Medford
The price is P13,810
P28,358 total
includes taxes & fees
Apr 12 - Apr 13
Rosewood Landing- Hot Tub- Sauna
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 P8,032
P19,471 total
includes taxes & fees
Apr 12 - Apr 13
Jville Gem- Walk downtown
Toys

Rosewood Collective- House & Studio

Rosewood Collective- House & Studio
3.0 star property
Medford
The price is P18,031
P37,177 total
includes taxes & fees
Apr 12 - Apr 13
Rosewood Collective- House & Studio
Outdoor dining

Meadowsweet Farm by WanderLodges

Meadowsweet Farm by WanderLodges
3.0 star property
Medford
The price is P21,649
P39,051 total
includes taxes & fees
Apr 12 - Apr 13
Meadowsweet Farm 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 P7,176
P16,146 total
includes taxes & fees
Apr 9 - Apr 10
Starwood Sanctuary
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 P5,186
P11,067 total
includes taxes & fees
Apr 12 - Apr 13
On-site Winery & Tasting Room: Oregon Bungalow!
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 P6,459
P15,306 total
includes taxes & fees
Apr 9 - Apr 10
Lanka Rose House by WanderLodges
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 P6,969
P16,077 total
includes taxes & fees
Apr 15 - Apr 16
Paschal Winery
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 P9,830
P15,706 total
includes taxes & fees
Apr 9 - Apr 10
The Rellik House and Winery
4 bedrooms

The Eagles Nest in Eagle Point

The Eagles Nest in Eagle Point
2.0 star property
Eagle Point
The price is P14,382
P26,983 total
includes taxes & fees
Apr 9 - Apr 10
The Eagles Nest in Eagle Point
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 P7,538
P16,553 total
includes taxes & fees
Apr 9 - Apr 10
Clearview Comfort 3BR Near Airport
Private kitchenette

Rosewood Studio by WanderLodges

Rosewood Studio by WanderLodges
3.0 star property
Medford
The price is P5,729
P9,498 total
includes taxes & fees
Apr 22 - Apr 23
Rosewood Studio by WanderLodges
3 bedrooms

Quail Run River View Cottage

Quail Run River View Cottage
2.0 star property
Jacksonville
Quail Run River View Cottage
Room

Luxury Gold Miner Cottage Walk to Britt

Luxury Gold Miner Cottage Walk to Britt
2.0 star property
Jacksonville
The price is P9,082
P16,088 total
includes taxes & fees
Apr 9 - Apr 10
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.
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Top Ashland Hotel Reviews

Timbers INN and Suites

Timbers INN and Suites

10/10 Excellent
"This was such a cute retro hotel. Perfect for a one night stop. It had the best pizza place right next door and a grocery store within walking distance. We had our dog and they had a perfect little dog area too right outside of the animal friendly room. "
Jayna 1-night trip
Posted 5 hours ago
Timbers INN and 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:

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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 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 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 vacation rentals are there in Ashland?

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

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 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.