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Ashland Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

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, (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 P19,229
P31,955 total
includes taxes & fees
Jul 26 - Jul 27
Grandview of Ashland
Interior

Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District
Savage Upon Siskiyou
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 P14,716
P25,333 total
includes taxes & fees
Jul 20 - Jul 21
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 P13,980
P20,325 total
includes taxes & fees
Jul 28 - Jul 29
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 P13,236
P22,648 total
includes taxes & fees
Aug 9 - Aug 10
Barclay Klum 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, (46 reviews)
"Lovely hidden gem in Ashland, walking distance to great restaurants and the Oregon Shakespeare Festival. Wonderfully welcoming host and lovely grounds to help you relax."
United States
Thu Trang
The price is P10,953
P15,643 total
includes taxes & fees
Jul 27 - Jul 28
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, (440 reviews)
"Great location and beautiful surrounding scenery"
United States
Sofia
The price is P6,036
P6,851 total
includes taxes & fees
Jul 21 - Jul 22
Rocky Point Resort
Toys

Rosewood Collective- House & Studio

Rosewood Collective- House & Studio
3.0 star property
Medford
The price is P15,229
P32,986 total
includes taxes & fees
Jul 27 - Jul 28
Rosewood Collective- House & Studio
Flat-screen TV, fireplace

Rosewood Landing- Hot Tub- Sauna

Rosewood Landing- Hot Tub- Sauna
3.0 star property
Medford
The price is P13,236
P27,974 total
includes taxes & fees
Jul 27 - Jul 28
Rosewood Landing- Hot Tub- Sauna
Living area

Starwood Sanctuary

Starwood Sanctuary
3.0 star property
Medford
10.0 out of 10, Exceptional, (2 reviews)
"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 P9,913
P19,390 total
includes taxes & fees
Aug 11 - Aug 12
Starwood Sanctuary
Private kitchen

Paschal Winery

Paschal Winery
4.5 star property
Talent
9.8 out of 10, Exceptional, (19 reviews)
"Incredible experience, fabulous wine, wish we had stayed longer to soak in the beauty of the experience. "
United States
Frankie
The price is P8,584
P26,062 total
includes taxes & fees
Jul 20 - Jul 21
Paschal Winery
Living area

The Rellik House and Winery

The Rellik House and Winery
3.5 star property
Central Point
9.2 out of 10, Wonderful, (5 reviews)
"A perfect place to enjoy the winery and countryside! Staff were responsive and friendly!"
United States
Kimberlee
The price is P11,937
P22,734 total
includes taxes & fees
Jul 22 - Jul 23
The Rellik House and Winery
Interior

Forest Cabin by Crater Lake & Klamath Falls

Forest Cabin by Crater Lake & Klamath Falls
3.0 star property
Klamath Falls
The price is P8,368
P14,933 total
includes taxes & fees
Aug 12 - Aug 13
Forest Cabin by Crater Lake & Klamath Falls
Outdoor dining

Meadowsweet Farm by WanderLodges

Meadowsweet Farm by WanderLodges
3.0 star property
Medford
The price is P19,229
P38,204 total
includes taxes & fees
Jul 22 - Jul 23
Meadowsweet Farm by WanderLodges
Private kitchenette

Rosewood Studio by WanderLodges

Rosewood Studio by WanderLodges
3.0 star property
Medford
The price is P7,255
P11,277 total
includes taxes & fees
Jul 27 - Jul 28
Rosewood Studio by WanderLodges
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

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

8/10 Good
"Pros: Room was clean and quiet. Bed was comfy. Front desk staff was super nice. Cons: Cat scratches all over the couch. Stove top and kitchenette in suite, but no dishes. Luna cafe has taken a complete nose dive - terrible service, long wait, bad coffee and mediocre food."
Korey 3-night trip
Posted 4 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:

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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 acclaimed theater scene 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 106 Expedia vacation rentals in Ashland for a memorable vacation.

What can I see and do in Ashland?

Cultural attractions include Allen Elizabethan Theatre and Angus Bowmer Theatre, whereas Lithia Park and Emigrant Lake are a couple of picturesque spots to enjoy the outdoors. Oregon Shakespeare Festival 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.