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Our top choices for Ashland holiday rentals

Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (3 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 ฿6,784
฿12,616 total
includes taxes & fees
21 Jan - 22 Jan
Grandview of Ashland

A Cowslip's Belle Inn

A Cowslip's Belle Inn
3.0 star property
Ashland
9.8 out of 10, Exceptional, (40 reviews)
"Lovely yard courtyard area with koi pond"
United States
Paul
The price is ฿4,250
฿6,494 total
includes taxes & fees
19 Jan - 20 Jan
A Cowslip's Belle Inn

Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (7 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is ฿3,917
฿8,553 total
includes taxes & fees
22 Jan - 23 Jan
Barclay Klum House by WanderLodges

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)
"This place was a 10/10! Made a big breakfast for my friends. Grocery store very close. I will be returning!"
United States
Montgomery
The price is ฿6,772
฿12,430 total
includes taxes & fees
16 Jan - 17 Jan
The Mountain Ave House by WanderLodges

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 ฿4,180
฿7,087 total
includes taxes & fees
5 Feb - 6 Feb
Hanna's House by WanderLodges

Clearview Comfort 3BR Near Airport

Clearview Comfort 3BR Near Airport
3.0 star property
Medford
10.0 out of 10, Exceptional, (2 reviews)
"The house is clean. There is 1 driveway parking, however street parking is available. Location is good, there are many dining and grocery options nearby."
United States
Phuc
The price is ฿4,845
฿10,020 total
includes taxes & fees
15 Feb - 16 Feb
Clearview Comfort 3BR Near Airport

Starwood Sanctuary

Starwood Sanctuary
3.0 star property
Medford
10.0 out of 10, Exceptional, (1 review)
"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 ฿5,072
฿9,920 total
includes taxes & fees
15 Feb - 16 Feb
Starwood Sanctuary

Lanka Rose House by WanderLodges

Lanka Rose House by WanderLodges
3.5 star property
Phoenix
10.0 out of 10, Exceptional, (2 reviews)
"Very cute house with all the necessities for a cozy stay. "
United States
Roxanne
The price is ฿3,774
฿8,423 total
includes taxes & fees
18 Jan - 19 Jan
Lanka Rose House by WanderLodges

Rosewood Collective- House & Studio

Rosewood Collective- House & Studio
3.0 star property
Medford
The price is ฿8,771
฿18,703 total
includes taxes & fees
29 Jan - 30 Jan
Rosewood Collective- House & Studio

Paschal Winery

Paschal Winery
4.5 star property
Talent
9.6 out of 10, Exceptional, (15 reviews)
"Great space and beautiful views. 10/10 experience. "
United States
Cody
The price is ฿4,023
฿7,075 total
includes taxes & fees
9 Feb - 10 Feb
Paschal Winery

Rosewood Landing- Hot Tub- Sauna

Rosewood Landing- Hot Tub- Sauna
3.0 star property
Medford
The price is ฿8,118
฿15,839 total
includes taxes & fees
18 Jan - 19 Jan
Rosewood Landing- Hot Tub- Sauna

On-site Winery & Tasting Room: Oregon Bungalow!

On-site Winery & Tasting Room: Oregon Bungalow!
3.0 star property
Central Point
8.4 out of 10, Very good, (5 reviews)
"Loved our stay at the Bungalow. The owners were so welcoming, helpful and friendly. The bungalow was very clean and had well equipped. It wa a great location for everything we wanted to do. The bungalow was even nicer than the pictures. We would definitely recommend this stay! "
United States
Deborah
The price is ฿2,707
฿5,973 total
includes taxes & fees
15 Feb - 16 Feb
On-site Winery & Tasting Room: Oregon Bungalow!

Meadowsweet Farm by WanderLodges

Meadowsweet Farm by WanderLodges
3.0 star property
Medford
The price is ฿11,894
฿21,004 total
includes taxes & fees
26 Jan - 27 Jan
Meadowsweet Farm by WanderLodges

The Rellik House and Winery

The Rellik House and Winery
3.5 star property
Central Point
9.4 out of 10, Exceptional, (3 reviews)
"A perfect place to enjoy the winery and countryside! Staff were responsive and friendly!"
United States
Kimberlee
The price is ฿4,618
฿7,678 total
includes taxes & fees
15 Feb - 16 Feb
The Rellik House and Winery

Medford Home and 2 Condos With Pool and Hot tub

Medford Home and 2 Condos With Pool and Hot tub
2.0 star property
Medford
The price is ฿2,528
฿7,018 total
includes taxes & fees
1 Feb - 2 Feb
Medford Home and 2 Condos With Pool and Hot tub

Rosewood Studio by WanderLodges

Rosewood Studio by WanderLodges
3.0 star property
Medford
The price is ฿3,548
฿5,588 total
includes taxes & fees
18 Jan - 19 Jan
Rosewood Studio by WanderLodges

Eagle Point Golf Retreat: Pool Access + Patio!

Eagle Point Golf Retreat: Pool Access + Patio!
3.5 star property
Eagle Point
The price is ฿4,258
฿11,623 total
includes taxes & fees
16 Jan - 17 Jan
Eagle Point Golf Retreat: Pool Access + Patio!

Medford Home and 2 Condos With Pool

Medford Home and 2 Condos With Pool
2.0 star property
Medford
The price is ฿10,003
฿25,924 total
includes taxes & fees
2 Feb - 3 Feb
Medford Home and 2 Condos With Pool
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

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 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 101 Expedia holiday rentals in Ashland for a memorable holiday.

What can I see and do in Ashland?

Cultural attractions include Allen Elizabethan Theatre and Oregon Shakespeare Festival, whereas Lithia Park and North Mountain Park are a couple of picturesque spots to enjoy the outdoors. Oregon Cabaret Theatre 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.