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Ashland Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Ashland vacation rentals

A bedroom with a large bed, a dresser, a mirror, a chandelier, and a staircase leading to another room.

1. Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (10 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is P8,082
P17,064 total
includes taxes & fees
Oct 18 - Oct 19
Barclay Klum House by WanderLodges
A modern kitchen with wooden beams, a dining area with a rug, and a large island.

2. The Mountain Ave House by WanderLodges

The Mountain Ave House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (8 reviews)
"Lovely space and very comfortable; walkable from downtown "
United States
Joyce
The price is P13,502
P24,157 total
includes taxes & fees
Oct 18 - Oct 19
The Mountain Ave House by WanderLodges
A cozy living room with a built-in bench, a flat-screen TV, a bookshelf, and a vase of flowers.

3. Hanna's House by WanderLodges

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (5 reviews)
"Very cute cottage, 10 min walk to OSF theaters. It has everything you need - full kitchen, front room, and AC for the hot summers! Owner very kind. Will stay there again!"
United States
Robert
The price is P7,815
P13,546 total
includes taxes & fees
Oct 18 - Oct 19
Hanna's House by WanderLodges
A staircase with wooden balusters, a round glass table with chairs, a patterned rug, and a white door with a decorative valance.

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 P14,381
P26,468 total
includes taxes & fees
Oct 25 - Oct 26
Savage Upon Siskiyou
A deck with a fire pit, outdoor seating, and a view of the countryside.

5. Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (11 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 P13,508
P26,395 total
includes taxes & fees
Oct 20 - Oct 21
Grandview of Ashland
A spacious kitchen with a central island, bar stools, and a fireplace.

6. 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 P8,760
P26,598 total
includes taxes & fees
Oct 19 - Oct 20
Paschal Winery
A clear view of a lake with a mountain in the background, a dock, and a chair on a deck.

7. Rocky Point Resort

Rocky Point Resort
2.5 star property
Klamath Falls
8.2 out of 10, Very good, (516 reviews)
"We enjoyed staying there Good location"
United States
Siranush
The price is P5,369
P6,094 total
includes taxes & fees
Oct 18 - Oct 19
Rocky Point Resort
A kitchen with a stainless steel sink, wooden cabinets, a black stove, and a window with curtains.

8. Rosewood Studio by WanderLodges

Rosewood Studio by WanderLodges
3.0 star property
Medford
The price is P6,056
P9,996 total
includes taxes & fees
Oct 19 - Oct 20
Rosewood Studio by WanderLodges
A modern living room with a grey sofa, wooden flooring, a flat-screen TV, a desk with a chair, and a patterned rug.

9. 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 P8,082
P17,500 total
includes taxes & fees
Oct 27 - Oct 28
Starwood Sanctuary
A spacious living room with a wooden floor, a dining table, a sofa, and a TV.

10. Rosewood Collective- House & Studio

Rosewood Collective- House & Studio
3.0 star property
Medford
Rosewood Collective- House & Studio
A modern living room with a wooden floor, a sofa, a coffee table, and a kitchen area in the background.

11. 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 P12,200
P23,233 total
includes taxes & fees
Nov 1 - Nov 2
The Rellik House and Winery
A signpost with the word "Canowinga" indicating a location.

12. Forest Cabin by Crater Lake & Klamath Falls

Forest Cabin by Crater Lake & Klamath Falls
3.0 star property
Klamath Falls
10.0 out of 10, Exceptional, (2 reviews)
"Thank you, this was a very clean, attractive property with everything needed. Maricio was the host & he was very attentive, kind & quick to respond . I highly recommend this property, it’s in a nice area & fun places to explore. Thanks for a great visit!"
United States
Jayne
The price is P7,473
P14,071 total
includes taxes & fees
Oct 27 - Oct 28
Forest Cabin by Crater Lake & Klamath Falls
A spacious living room with a wooden floor, a dining table, a sofa, and a TV.

13. Rosewood Landing- Hot Tub- Sauna

Rosewood Landing- Hot Tub- Sauna
3.0 star property
Medford
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

8/10 Good
"The room was clean and the bed was comfortable. However, the pillows are in dire need for an upgrade. And the bathroom could use a renovation. The hotel is very convenient for attending the theater at the Shakespeare Festival, and is also a short walk to all of the area restaurants. In addition, it was very convenient to have two free, electric car chargers in the parking lot."
Christopher 4-night trip
Posted 9 hours ago
The Bard's Inn, BW Signature Collection by Best Western

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:

  • View our selection of featured holiday rentals in Ashland
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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 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.