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Check prices for these dates

Tonight
16 Aug - 17 Aug
Tomorrow
17 Aug - 18 Aug
Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug

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, (35)
"What a wonderful place to stay! The owners were very cordial and offered suggestion about places to go. We particularly loved to Koi pond right off our deck. "
The price is 5.113.188 ₫
7.165.868 ₫ total
includes taxes & fees
25 Aug - 26 Aug
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, (5)
"Great ~ memorable stay. "
The price is 3.972.326 ₫
7.829.603 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Barclay Klum House by WanderLodges
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, (1)
"If I were single I could live here. It's that comfortable. The freestanding apartment is ideally located and finished to a very high standard. Amazingly well designed and laid out. Full kitchen, living room, bedroom, and bath. Many, many conveniences. Cafe table in garden outside. We parked once and walked everywhere. Lovely host. Really, I can't imagine anyone giving it less than a perfect score. Would definitely stay here again."
The price is 3.279.534 ₫
5.695.737 ₫ total
includes taxes & fees
19 Aug - 20 Aug
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
Hiking Trail On-site: Mtn-view Eagle Point Retreat
House (1 Bedroom) | Interior

Hiking Trail On-site: Mtn-view Eagle Point Retreat

3.0 star property
10.0 out of 10, Exceptional, (2)
"Very cute and cozy place to stay in the country. We met a bunch of wild turkey and deer in trip back and forth to home. The place was clean, inviting and privare. Enjoyed our stay!"
Hiking Trail On-site: Mtn-view Eagle Point Retreat
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 7.863.551 ₫
13.602.810 ₫ total
includes taxes & fees
15 Sept - 16 Sept
Grandview of Ashland
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
Whispering Pines Cabin Retreat
Chalet (3 Bedrooms) | Private kitchen | Full-sized fridge, microwave, oven, stovetop

Whispering Pines Cabin Retreat

3.5 star property
Whispering Pines Cabin Retreat
Ashland Lodge w/ Lake Views & Game Room Loft
House (4 Bedrooms) | Front of property

Ashland Lodge w/ Lake Views & Game Room Loft

3.0 star property
Ashland Lodge w/ Lake Views & Game Room Loft
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
9.0 out of 10, Wonderful, (21)
"Great space to relax, bed was comfy, property was clean and quiet. Awesome spot, would definitely stay again."
Peach Street Inn by WanderLodges
Rocky Point Resort
Sun deck

Rocky Point Resort

2.5 star property
8.2 out of 10, Very good, (365)
"Great stay!"
The price is 2.577.283 ₫
2.925.124 ₫ total
includes taxes & fees
21 Aug - 22 Aug
Rocky Point Resort
Paschal Winery
Glamp Cottage Trailer | Living area | Flat-screen TV, fireplace

Paschal Winery

4.5 star property
9.6 out of 10, Exceptional, (10)
"Very nice and hassle free check in "
The price is 4.587.091 ₫
7.151.737 ₫ total
includes taxes & fees
18 Aug - 19 Aug
Paschal Winery
Enchanting Getaway: Farmhouse and Tiny House Duo
House

Enchanting Getaway: Farmhouse and Tiny House Duo

2.0 star property
The price is 2.452.744 ₫
20.308.692 ₫ total
includes taxes & fees
26 Aug - 27 Aug
Enchanting Getaway: Farmhouse and Tiny House Duo
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 4.587.091 ₫
9.647.577 ₫ total
includes taxes & fees
15 Sept - 16 Sept
The Rellik House and Winery
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, (1)
"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
Medford Home and 2 Condos With Pool and Hot tub
Apartment

Medford Home and 2 Condos With Pool and Hot tub

2.0 star property
The price is 2.615.056 ₫
24.772.743 ₫ total
includes taxes & fees
17 Aug - 18 Aug
Medford Home and 2 Condos With Pool and Hot tub
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
"Beautiful grounds surrounding the property. Little dissapointed spa is gone but got over that quickly."
Gary 1-night trip
Posted 21 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 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 131 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 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.