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Ashland Vacation Rentals

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Check prices for these dates

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

Our top choices for Ashland vacation rentals

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 P11,083
P15,829 total
includes taxes & fees
Sep 7 - Sep 8
A Cowslip's Belle Inn
Room

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 P8,686
P17,668 total
includes taxes & fees
Sep 1 - Sep 2
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 P12,720
P25,487 total
includes taxes & fees
Sep 13 - Sep 14
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 P14,258
P26,242 total
includes taxes & fees
Sep 1 - Sep 2
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 P10,588
P16,596 total
includes taxes & fees
Sep 10 - Sep 11
Hanna's House by WanderLodges
Living area

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 P11,145
P21,452 total
includes taxes & fees
Sep 1 - Sep 2
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, (478 reviews)
"Great location."
United States
Noni
The price is P5,323
P6,042 total
includes taxes & fees
Sep 9 - Sep 10
Rocky Point Resort
Private kitchenette

8. Rosewood Studio by WanderLodges

Rosewood Studio by WanderLodges
3.0 star property
Medford
The price is P6,668
P10,654 total
includes taxes & fees
Sep 1 - Sep 2
Rosewood Studio by WanderLodges
Private kitchen

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 P8,686
P26,371 total
includes taxes & fees
Sep 1 - Sep 2
Paschal Winery
Living area

10. Rosewood Collective- House & Studio

Rosewood Collective- House & Studio
3.0 star property
Medford
The price is P16,755
P34,890 total
includes taxes & fees
Sep 29 - Sep 30
Rosewood Collective- House & Studio
Front of property

11. Forest Cabin by Crater Lake & Klamath Falls

Forest Cabin by Crater Lake & Klamath Falls
3.0 star property
Klamath Falls
The price is P6,787
P13,269 total
includes taxes & fees
Sep 10 - Sep 11
Forest Cabin by Crater Lake & Klamath Falls
Outdoor dining

12. Meadowsweet Farm by WanderLodges

Meadowsweet Farm by WanderLodges
3.0 star property
Medford
The price is P15,410
P34,537 total
includes taxes & fees
Sep 1 - Sep 2
Meadowsweet Farm by WanderLodges
Living area

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 P14,507
P25,468 total
includes taxes & fees
Sep 2 - Sep 3
The Rellik House and Winery
Living area

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 P8,013
P17,350 total
includes taxes & fees
Sep 7 - Sep 8
Starwood Sanctuary
Living area

15. Rosewood Landing- Hot Tub- Sauna

Rosewood Landing- Hot Tub- Sauna
3.0 star property
Medford
The price is P10,031
P24,523 total
includes taxes & fees
Sep 6 - Sep 7
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

Best Western Windsor Inn

Best Western Windsor Inn

10/10 Excellent
"The room was very clean and the staff very helpful."
May 1-night trip
Posted 1 hour ago
Best Western Windsor Inn

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 entertainment choices 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 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 Oregon Shakespeare Festival, whereas Lithia Park and Emigrant Lake are a couple of picturesque spots to enjoy the outdoors. Oregon Cabaret Theatre and Ashland Library 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.