Search Holiday Rentals in Ashland

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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

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 3.247.599 ₫
7.115.863 ₫ 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
1 Jan - 2 Jan 2026
A Cowslip's Belle Inn
Grand House | Living area | 65-inch TV with digital channels, streaming services
The Mountain Ave 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)
"Lovely space and very comfortable; walkable from downtown "
United States
Joyce
The price is 4.243.213 ₫
8.813.333 ₫ total
includes taxes & fees
21 Dec - 22 Dec
The Mountain Ave House by WanderLodges
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
23 Dec - 24 Dec
Hanna's House by WanderLodges
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

McCall House Boutique Inn

McCall House Boutique Inn

10/10 Excellent
" We had a wonderful stay. Beautiful home with lovely decor. Staff were very attentive and friendly."
Tanja 2-night trip
Posted 3 days ago
McCall House Boutique 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.