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Check prices for these dates

Tonight
18 Dec - 19 Dec
Tomorrow
19 Dec - 20 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for Ashland holiday rentals

Sun deck
Grandview of Ashland

Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (2)
"I absolutely fell in love with this property it was so beautiful from the moment we drove up the hill to see this gorgeous house at the top. The yard and garden was a surprise. I wasn’t expecting to have such a peaceful place to stay the pictures don’t even do it justice. I would definitely Want to stay there again when I come to visit family. "
United States
Monica
The price is 5.663.798 ₫
10.532.703 ₫ total
includes taxes & fees
12 Jan - 13 Jan 2026
Grandview of Ashland
Luxury House, 2 Bedrooms, Bathtub, Garden Area | Living area
Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (7)
"Great ~ memorable stay. "
United States
Melissa
The price is 3.388.800 ₫
7.272.241 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
Barclay Klum House by WanderLodges
Terrace/patio
A Cowslip's Belle Inn

A Cowslip's Belle Inn

A Cowslip's Belle Inn
3.0 star property
Ashland
9.8 out of 10, Exceptional, (40)
"Lovely yard courtyard area with koi pond"
United States
Paul
The price is 3.554.685 ₫
5.431.427 ₫ total
includes taxes & fees
22 Dec - 23 Dec
A Cowslip's Belle Inn
Interior detail
Hanna's 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)
"Thoughtfully arranged and provisioned. A hidden gem."
United States
Jerald
The price is 2.949.204 ₫
5.314.139 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Hanna's House by WanderLodges
Chalet (3 Bedrooms) | Living area | TV, fireplace
Sunset Chalet - 2600 Sq.ft. Multi-seasonal Retreat

Sunset Chalet - 2600 Sq.ft. Multi-seasonal Retreat

Sunset Chalet - 2600 Sq.ft. Multi-seasonal Retreat
3.5 star property
Ashland
Sunset Chalet - 2600 Sq.ft. Multi-seasonal Retreat
House (4 Bedrooms) | Interior
Private Pool & Mtn Views: Stunning Ashland Home

Private Pool & Mtn Views: Stunning Ashland Home

Private Pool & Mtn Views: Stunning Ashland Home
3.0 star property
Ashland
Private Pool & Mtn Views: Stunning Ashland Home
View from property
Rocky Point Resort

Rocky Point Resort

Rocky Point Resort
2.5 star property
Klamath Falls
8.2 out of 10, Very good, (405)
"Room was clean,everything was properly cleaned and had a professional presentation!! "
United States
Sonny
The price is 2.251.301 ₫
2.555.161 ₫ total
includes taxes & fees
20 Dec - 21 Dec
Rocky Point Resort
Glamp Cottage Trailer | Living area | Flat-screen TV, fireplace
Paschal Winery

Paschal Winery

Paschal Winery
4.5 star property
Talent
9.6 out of 10, Exceptional, (15)
"Very nice and hassle free check in "
United States
Matthew
The price is 3.365.102 ₫
5.917.024 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Paschal Winery
Deluxe Suite | Living area | 50-inch flat-screen TV with cable channels
The Rellik House and Winery

The Rellik House and Winery

The Rellik House and Winery
3.5 star property
Central Point
9.4 out of 10, Exceptional, (3)
"A perfect place to enjoy the winery and countryside! Staff were responsive and friendly!"
United States
Kimberlee
The price is 3.862.758 ₫
6.422.144 ₫ total
includes taxes & fees
18 Jan - 19 Jan 2026
The Rellik House and Winery
Studio, 1 Queen Bed, Kitchenette | Private kitchenette | Coffee/tea maker, electric kettle, toaster, paper towels
Rosewood Studio by WanderLodges

Rosewood Studio by WanderLodges

Rosewood Studio by WanderLodges
3.0 star property
Medford
The price is 3.291.375 ₫
5.035.803 ₫ total
includes taxes & fees
20 Dec - 21 Dec
Rosewood Studio by WanderLodges
Apartment | 6 bedrooms
Medford Home and 2 Condos With Pool and Hot tub

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 2.352.002 ₫
5.959.525 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Medford Home and 2 Condos With Pool and Hot tub
35-inch Smart TV with digital channels, Netflix, Hulu
Lanka Rose House by WanderLodges

Lanka Rose House by WanderLodges

Lanka Rose House by WanderLodges
3.5 star property
Phoenix
10.0 out of 10, Exceptional, (1)
"Very cute house with all the necessities for a cozy stay. "
United States
Roxanne
The price is 2.921.951 ₫
6.792.548 ₫ total
includes taxes & fees
20 Dec - 21 Dec
Lanka Rose House by WanderLodges
House | 3 bedrooms
Enchanting Getaway: Farmhouse and Tiny House Duo

Enchanting Getaway: Farmhouse and Tiny House Duo

Enchanting Getaway: Farmhouse and Tiny House Duo
2.0 star property
Jacksonville
The price is 2.420.895 ₫
6.171.365 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Enchanting Getaway: Farmhouse and Tiny House Duo
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
"Clean. Good breakfast."
Gary 1-night trip
Posted 4 days ago
Best Western Windsor Inn

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 103 Expedia holiday rentals in Ashland for a memorable holiday.

What can I see and do in Ashland?

Cultural attractions include Thomas Theatre and Oregon Shakespeare Festival, whereas Lithia Park and Howard Prairie Lake 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.