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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec
In four months
23 Jan - 25 Jan

Top Holiday Rentals in Ashland

A Cowslip's Belle Inn
Main House | Terrace/patio

A Cowslip's Belle Inn

3.0 star property
9.8 out of 10, Exceptional, (38)
"Lovely yard courtyard area with koi pond"
The price is 4.628.551 ₫
6.634.028 ₫ total
includes taxes & fees
6 Oct - 7 Oct
A Cowslip's Belle Inn
Barclay Klum House by WanderLodges
Luxury House, 2 Bedrooms, Bathtub, Garden Area | Private kitchen | Full-sized fridge, microwave, oven, stovetop

Barclay Klum House by WanderLodges

4.0 star property
10.0 out of 10, Exceptional, (6)
"Great ~ memorable stay. "
The price is 4.280.850 ₫
8.213.101 ₫ total
includes taxes & fees
6 Oct - 7 Oct
Barclay Klum House by WanderLodges
Grandview of Ashland
Terrace/patio

Grandview of Ashland

3.0 star property
10.0 out of 10, Exceptional, (1)
"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. "
The price is 7.907.550 ₫
13.678.922 ₫ total
includes taxes & fees
2 Oct - 3 Oct
Grandview of Ashland
Hanna's House by WanderLodges
City Bungalow, Garden Area | Private kitchen | Oven, stovetop, dishwasher, toaster

Hanna's House by WanderLodges

4.0 star property
10.0 out of 10, Exceptional, (2)
"This is a true gem!!! "
The price is 3.907.766 ₫
6.449.707 ₫ total
includes taxes & fees
6 Oct - 7 Oct
Hanna's House by WanderLodges
232 4th Street
Duplex, Private Bathroom, Mountain View (232) | Lounge

232 4th Street

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great location with easy access to downtown Ashland. We were able to walk nearly everywhere we wanted to go and enjoyed the neighborhood shops. Overall the neighborhood was quiet and the accommodations were what we wanted. "
232 4th Street
Sunset Chalet - 2600 Sq.ft. Multi-seasonal Retreat
Chalet (3 Bedrooms) | Living area | TV, fireplace

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

3.5 star property
Sunset Chalet - 2600 Sq.ft. Multi-seasonal Retreat
Rocky Point Resort
Sun deck

Rocky Point Resort

2.5 star property
8.2 out of 10, Very good, (381)
"We really enjoyed our stay at Rocky Point. The room was comfortable and the area is beautiful. "
The price is 2.591.704 ₫
2.941.492 ₫ total
includes taxes & fees
5 Oct - 6 Oct
Rocky Point Resort
Peach Street Inn by WanderLodges
Suite #4, 2 beds, Sleeps 4 | Private kitchen | Fridge, microwave, oven, stovetop

Peach Street Inn by WanderLodges

2.0 star property
9.2 out of 10, Wonderful, (26)
"Very nice property and rooms are spacious and clean. Will definitely return,"
Peach Street Inn by WanderLodges
Paschal Winery
Glamp Cottage Trailer | Living area | Flat-screen TV, fireplace

Paschal Winery

4.5 star property
9.6 out of 10, Exceptional, (11)
"Very nice and hassle free check in "
The price is 3.376.348 ₫
5.936.798 ₫ total
includes taxes & fees
13 Oct - 14 Oct
Paschal Winery
The Rellik House and Winery
Deluxe Suite | Living area | 50-inch flat-screen TV with cable channels

The Rellik House and Winery

3.5 star property
9.4 out of 10, Exceptional, (3)
"A perfect place to enjoy the winery and countryside! Staff were responsive and friendly!"
The price is 4.613.805 ₫
7.193.387 ₫ total
includes taxes & fees
30 Oct - 31 Oct
The Rellik House and Winery
Enchanting Getaway: Farmhouse and Tiny House Duo
House | 3 bedrooms

Enchanting Getaway: Farmhouse and Tiny House Duo

2.0 star property
The price is 2.540.909 ₫
6.310.501 ₫ total
includes taxes & fees
5 Oct - 6 Oct
Enchanting Getaway: Farmhouse and Tiny House Duo
Rosewood Studio by WanderLodges
Studio, 1 Queen Bed, Kitchenette | Private kitchenette | Coffee/tea maker, electric kettle, toaster, paper towels

Rosewood Studio by WanderLodges

3.0 star property
The price is 3.619.403 ₫
5.260.683 ₫ total
includes taxes & fees
14 Oct - 15 Oct
Rosewood Studio by WanderLodges
Remote Escape: Klamath Falls Cabin By Lake & Hikes
House (1 Bedroom) | Interior

Remote Escape: Klamath Falls Cabin By Lake & Hikes

2.0 star property
10.0 out of 10, Exceptional, (2)
"The cabin was amazing! Very cool log cabin vibe with all of the decorations to make you feel like you're roughing it in the woods but with all the modern convenience to make it comfortable. The outdoor bathtub and grilling area were standouts. The cabin actually does have AC even though the listing says it doesn't so that was a relief for a summer getaway. We came to see Crater Lake and it was close enough to recommend it for anyone wanting to see crater along with lake activities closer by at...
Remote Escape: Klamath Falls Cabin By Lake & Hikes
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

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

10/10 Excellent
"Great clean spacious rooms with a cool retro vibe"
Richard 1-night trip
Posted 22 hours ago
Ashland Hills Hotel & Suites

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 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 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 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 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.