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Top Holiday Rentals in Ashland

A Cowslip's Belle Inn

3.0 star property
9.8 out of 10, Exceptional, (33)
"Terrific communication with owners, lovely property and close to downtown shops, theatre, etc. Highly recommend!"
The price is ฿7,046
฿9,673 total
includes taxes & fees
28 Jul - 29 Jul
A Cowslip's Belle Inn

Barclay Klum House by WanderLodges

4.0 star property
10.0 out of 10, Exceptional, (5)
"Great ~ memorable stay. "
The price is ฿6,762
฿11,894 total
includes taxes & fees
4 Aug - 5 Aug
Barclay Klum House by WanderLodges

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 ฿4,301
฿7,347 total
includes taxes & fees
10 Aug - 11 Aug
Hanna's House by WanderLodges

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

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

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 ฿10,104
฿17,245 total
includes taxes & fees
4 Aug - 5 Aug
Grandview of Ashland

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

3.5 star property
Sunset Chalet - 2600 Sq.ft. Multi-seasonal Retreat

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

2.0 star property
9.4 out of 10, Exceptional, (13)
"Great space to relax, bed was comfy, property was clean and quiet. Awesome spot, would definitely stay again."
Peach Street Inn by WanderLodges

Paschal Winery

4.5 star property
9.6 out of 10, Exceptional, (10)
"Very nice and hassle free check in "
The price is ฿5,704
฿8,893 total
includes taxes & fees
13 Jul - 14 Jul
Paschal Winery

Rocky Point Resort

2.5 star property
8.2 out of 10, Very good, (359)
"Phenomenal experience and value for the price! "
Rocky Point Resort

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 ฿5,704
฿11,996 total
includes taxes & fees
10 Aug - 11 Aug
The Rellik House and Winery

Enchanting Getaway: Farmhouse and Tiny House Duo

2.0 star property
The price is ฿3,558
฿7,309 total
includes taxes & fees
22 Jul - 23 Jul
Enchanting Getaway: Farmhouse and Tiny House Duo

Medford Home and 2 Condos With Pool and Hot tub

2.0 star property
The price is ฿4,169
฿11,555 total
includes taxes & fees
29 Jul - 30 Jul
Medford Home and 2 Condos With Pool and Hot tub

Remote Escape: Klamath Falls Cabin By Lake & Hikes

2.0 star property
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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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 renowned opera 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 132 Expedia holiday rentals in Ashland for a memorable holiday.

What can I see and do in Ashland?

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