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Ashland Vacation Rentals

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Ashland vacation rentals

Rosebud | Terrace/patio

1. A Cowslip's Belle Inn

A Cowslip's Belle Inn
3.0 star property
Ashland
9.6 out of 10, Exceptional, (52 reviews)
"Fantastic location, wonderful amenities. Would absolutely stay here again!!"
United States
Daniel
The price is SAR 752
SAR 1,048 total
includes taxes & fees
31 Aug - 1 Sep
A Cowslip's Belle Inn
Luxury House, 2 Bedrooms, Bathtub, Garden Area | 2 bedrooms, laptop workspace, iron/ironing board, WiFi (free)

2. Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (9 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is SAR 482
SAR 1,019 total
includes taxes & fees
1 Sep - 2 Sep
Barclay Klum House by WanderLodges
Sundeck

3. Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (9 reviews)
"The Grandview house and property far exceeded our expectations. We especially enjoying making meals together in the beautiful kitchen and reminiscing on the deck while taking in the spectacular views. We were fortunate to see lots of wildlife too. We hope to come back next year."
United States
Sonja
The price is SAR 729
SAR 1,498 total
includes taxes & fees
14 Sep - 15 Sep
Grandview of Ashland
Interior

4. Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Had an amazing stay, thank you!"
United States
megan
The price is SAR 860
SAR 1,582 total
includes taxes & fees
31 Aug - 1 Sep
Savage Upon Siskiyou
Interior detail

5. Hanna's House by WanderLodges

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (4 reviews)
"Next visit to the OSF no question we’ll stay here if available. Short walking distance to everything in downtown Ashland, yet quiet and private."
United States
David
The price is SAR 638
SAR 1,001 total
includes taxes & fees
10 Sep - 11 Sep
Hanna's House by WanderLodges
Grand House | Living area | 65-inch TV with digital channels, streaming services

6. 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 SAR 672
SAR 1,294 total
includes taxes & fees
31 Aug - 1 Sep
The Mountain Ave House by WanderLodges
View from property

7. Rocky Point Resort

Rocky Point Resort
2.5 star property
Klamath Falls
8.2 out of 10, Very Good, (476 reviews)
The price is SAR 321
SAR 364 total
includes taxes & fees
9 Sep - 10 Sep
Rocky Point Resort
Studio, 1 Queen Bed, Kitchenette | Private kitchenette | Coffee/tea maker, electric kettle, toaster, paper towels

8. Rosewood Studio by WanderLodges

Rosewood Studio by WanderLodges
3.0 star property
Medford
The price is SAR 402
SAR 642 total
includes taxes & fees
31 Aug - 1 Sep
Rosewood Studio by WanderLodges
House | Private kitchen | Full-size fridge, microwave, oven, stovetop

9. Paschal Winery

Paschal Winery
4.5 star property
Talent
9.8 out of 10, Exceptional, (19 reviews)
"Stunning scenery, great wine and food. Friendly, helpful people on site and the hot tub is blissfully perfect ❤️"
United States
Christine
The price is SAR 482
SAR 1,548 total
includes taxes & fees
1 Sep - 2 Sep
Paschal Winery
Toys

10. Rosewood Collective- House & Studio

Rosewood Collective- House & Studio
3.0 star property
Medford
The price is SAR 767
SAR 1,830 total
includes taxes & fees
31 Aug - 1 Sep
Rosewood Collective- House & Studio
House (0 Bedroom) | Interior

11. Forest Cabin by Crater Lake & Klamath Falls

Forest Cabin by Crater Lake & Klamath Falls
3.0 star property
Klamath Falls
The price is SAR 409
SAR 800 total
includes taxes & fees
31 Aug - 1 Sep
Forest Cabin by Crater Lake & Klamath Falls
Family Villa, Multiple Bedrooms, Valley View | Outdoor dining

12. Meadowsweet Farm by WanderLodges

Meadowsweet Farm by WanderLodges
3.0 star property
Medford
The price is SAR 929
SAR 2,083 total
includes taxes & fees
31 Aug - 1 Sep
Meadowsweet Farm by WanderLodges
Deluxe Suite | Living area | 50-inch flat-screen TV with cable channels

13. The Rellik House and Winery

The Rellik House and Winery
3.5 star property
Central Point
9.4 out of 10, Exceptional, (6 reviews)
"A perfect place to enjoy the winery and countryside! Staff were responsive and friendly!"
United States
Kimberlee
The price is SAR 875
SAR 1,536 total
includes taxes & fees
2 Sep - 3 Sep
The Rellik House and Winery
Premium House, 3 Bedrooms, Pets Allowed | Living area | Flat-screen TV

14. Starwood Sanctuary

Starwood Sanctuary
3.0 star property
Medford
9.4 out of 10, Exceptional, (3 reviews)
"I was able to have early check in. The private bathroom off the main room was tiny. Coffee and cocoa were nice. The beds were comfy but the accent lights didn’t work and the shampoo dispenser was broken. Price and location were nice.. may book again.. spider webs outside 🤔😊"
United States
Erin
The price is SAR 483
SAR 1,046 total
includes taxes & fees
7 Sep - 8 Sep
Starwood Sanctuary
Flat-screen TV, fireplace

15. Rosewood Landing- Hot Tub- Sauna

Rosewood Landing- Hot Tub- Sauna
3.0 star property
Medford
The price is SAR 605
SAR 1,479 total
includes taxes & fees
7 Sep - 8 Sep
Rosewood Landing- Hot Tub- Sauna
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

The Bard's Inn, BW Signature Collection by Best Western

The Bard's Inn, BW Signature Collection by Best Western

10/10 Excellent
"Nice hotel and walking distance to shopping and restaurants"
Dawn 1-night trip
Posted 4 hours ago
The Bard's Inn, BW Signature Collection by Best Western

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 entertainment choices this destination is known for. Leave some time to check out the lively festivals and top-notch restaurants during your visit.

What are some of the best vacation rentals that Ashland has to offer?

Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly: This highly rated vacation home rental in Ashland offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. Some other homes for rent in Ashland include Beautiful bungalow downtown Ashland railroad district, rv parking, adventure! and Gorgeous Lakeside BarnHOUSE + SAUNA!.

How many vacation rentals are there in Ashland?

Choose from 108 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.