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Ashland Holiday Rentals

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Ashland holiday rentals

Sun deck

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 S$543
includes taxes & fees
15 Jul - 16 Jul
Grandview of Ashland
Interior

Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District
The price is S$545
includes taxes & fees
16 Jul - 17 Jul
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 S$532
includes taxes & fees
20 Jul - 21 Jul
The Mountain Ave 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 S$538
includes taxes & fees
2 Aug - 3 Aug
Barclay Klum 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 S$427
includes taxes & fees
28 Jul - 29 Jul
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, (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 S$361
includes taxes & fees
27 Jul - 28 Jul
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, (435 reviews)
"Hidden gem, very clean and gorgeous views."
United States
Dawn
The price is S$144
includes taxes & fees
16 Jul - 17 Jul
Rocky Point Resort
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 S$539
includes taxes & fees
9 Jul - 10 Jul
Paschal Winery
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 S$376
includes taxes & fees
26 Jul - 27 Jul
Starwood Sanctuary
Toys

Rosewood Collective- House & Studio

Rosewood Collective- House & Studio
3.0 star property
Medford
The price is S$693
includes taxes & fees
14 Jul - 15 Jul
Rosewood Collective- House & Studio
Outdoor dining

Meadowsweet Farm by WanderLodges

Meadowsweet Farm by WanderLodges
3.0 star property
Medford
The price is S$816
includes taxes & fees
20 Jul - 21 Jul
Meadowsweet Farm by WanderLodges
Flat-screen TV, fireplace

Rosewood Landing- Hot Tub- Sauna

Rosewood Landing- Hot Tub- Sauna
3.0 star property
Medford
The price is S$588
includes taxes & fees
14 Jul - 15 Jul
Rosewood Landing- Hot Tub- Sauna
Interior

Forest Cabin by Crater Lake & Klamath Falls

Forest Cabin by Crater Lake & Klamath Falls
3.0 star property
Klamath Falls
The price is S$284
includes taxes & fees
20 Jul - 21 Jul
Forest Cabin by Crater Lake & Klamath Falls
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 S$468
includes taxes & fees
4 Aug - 5 Aug
The Rellik House and Winery
Private kitchenette

Rosewood Studio by WanderLodges

Rosewood Studio by WanderLodges
3.0 star property
Medford
The price is S$237
includes taxes & fees
21 Jul - 22 Jul
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 Springs Hotel

Ashland Springs Hotel

10/10 Excellent
"Fantastic hotel in a cool town!"
Kevin 1-night trip
Posted less than an hour ago
Ashland Springs Hotel

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 acclaimed theatre scene 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 106 Expedia holiday rentals in Ashland for a memorable holiday.

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 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.