Holiday Rentals in Ashland

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Holiday Rentals in Ashland

A Cowslip's Belle Inn

3.0 star property
9.8 out of 10, Exceptional, (28)
"Awesome location, close to great dining and shopping venues"
The price is €212
includes taxes & fees
3 Dec - 4 Dec
A Cowslip's Belle Inn

Charming home, w/hot tub, close to downtown Pet-Friendly!

10.0 out of 10, Exceptional, (30)
"Very charming home with everything you need to relax and enjoy a vacation in Ashland, Oregon."
The price is €494
includes taxes & fees
3 Dec - 4 Dec
Charming home, w/hot tub, close to downtown Pet-Friendly!

Ashland Escape: Downtown & Pet Friendly

9.8 out of 10, Exceptional, (28)
"My husband and I have stayed at many of the rentals in Ashland over the years. We really enjoyed the location of Hellman House. One could walk just about anywhere to dine, have drinks, shop, visit famous Lythia Park. The home was clean, and the property manager was very responsive. My only nitpicky thought is that the upstairs bedroom doesn’t have a door. Kind of odd. Should be easy enough to add one. Our daughter and her fiancé stayed with us two nights, and so we had to be quiet downstairs as...
The price is €314
includes taxes & fees
24 Nov - 25 Nov
Ashland Escape: Downtown & Pet Friendly

Premier Downstairs Flat in Perfect Down Town Location

10.0 out of 10, Exceptional, (47)
"This was a beautiful and clean home in a perfect location. So close to downtown and the Shakespeare Festival. The walk was easy, well lite and safe. The home was clean and the beds were comfortable. We would definitely recommend and return!!"
Premier Downstairs Flat in Perfect Down Town Location

Railroad District, steps to downtown, everything you need to enjoy Ashland!

10.0 out of 10, Exceptional, (136)
"Clean. Tidy. comfortable. Well appointed. But we left a pair of walking polls behind and would like Sugar to keep them for us and we will pick them up when we stay again in the fall of 2025. David Roberts"
Railroad District, steps to downtown, everything you need to enjoy Ashland!

Hyatt Lake Mountain Retreat

9.8 out of 10, Exceptional, (75)
"Thoroughly enjoyed our time"
Hyatt Lake Mountain Retreat

Mt Ashland Log Cabin w/Swedish sauna by Pacific Crest Trail-15 min from Ashland

10.0 out of 10, Exceptional, (49)
"Tremendously happy to have discovered this jewel of a getaway! A peaceful paradise with a wonderful cabin to comfort us during our stay. There really is nothing better than the sound of pouring rain dancing on the roof top while listening to the snap-crackle-and-pop of the woodstove warming us up while we sip on hot chocolate with marshmellows..ahhh, relaxation at its best. And what a great host we had! Mich greeted us upon our arrival and instantly made us feel truly welcomed. She gave us a...
Mt Ashland Log Cabin w/Swedish sauna by Pacific Crest Trail-15 min from Ashland

The Red Dragon House

10.0 out of 10, Exceptional, (82)
"Mike and Mindy's place had everything we could ask for and more."
The price is €199
includes taxes & fees
23 Nov - 24 Nov
The Red Dragon House

Centrally located Siskiyou mountain house studio

6.8 out of 10, (3)
"Nice location and overall nice room. Had there not been someone who lived next door we would not have been able to open tbe door, the lock is so confusing. The mattress on the bed dips where people have slept on it. There were a few other things but they were more incidentals."
Centrally located Siskiyou mountain house studio

Courtside Cottage - WalkScore 93 - Dog Friendly

10.0 out of 10, Exceptional, (34)
"A clean cozy cottage perfectly located to enjoy Ashland."
The price is €220
includes taxes & fees
9 Dec - 10 Dec
Courtside Cottage - WalkScore 93 - Dog Friendly

Studio Retreat: Pet-Friendly Comfort

9.8 out of 10, Exceptional, (15)
"I liked everything about the place. Good use of a small space. I did recommend to the owner that the carpet and exterior need some attention and owner was very responsive. Inside decor is bright and cheery."
Studio Retreat: Pet-Friendly Comfort

The Ashland Cottage, walk to town

10.0 out of 10, Exceptional, (188)
"Nice cozy cottage It was private and peaceful We enjoyed our stay"
The price is €287
includes taxes & fees
1 Dec - 2 Dec
The Ashland Cottage, walk to town

City Comfort: 3BDR Walkable Retreat

10.0 out of 10, Exceptional, (13)
"Wonderful home with plenty of space and amenities for taking in a couple shows at the Ashland Shakespeare Festival. It's also under a 15 minute walk to any of the theatres. It is an older home (which is a lot of of the charm!) so the creaky wood floors will wake your travel partners should you go to bed at different times. Would stay again!"
City Comfort: 3BDR Walkable Retreat

Ashland's Mountain View Vacation Rental.

10.0 out of 10, Exceptional, (33)
"I was in town for a wedding. Stayed with a few friends and the place was perfect. Check in was very easy. The place was super clean. The beds were massive and soft. Make brunch each morning in the kitchen. Great stay! "
Ashland's Mountain View Vacation Rental.

Hyatt Praire Mountain Cabin

10.0 out of 10, Exceptional, (48)
"Beautiful location up in the pine trees. The interior of the cabin felt modern and very clean. "
The price is €405
includes taxes & fees
24 Nov - 25 Nov
Hyatt Praire Mountain Cabin

Queen Suite | Hot Tub | Downtown Ashland | Tesla Station

10.0 out of 10, Exceptional, (7)
"A lovely unit! "
The price is €229
includes taxes & fees
24 Nov - 25 Nov
Queen Suite | Hot Tub | Downtown Ashland | Tesla Station

1 Bedroom Suite | Hot Tub | Downtown Ashland | Tesla Station

8.0 out of 10, Very good, (2)
"We love the location and especially the restaurant next door! Thank you!"
The price is €259
includes taxes & fees
23 Nov - 24 Nov
1 Bedroom Suite | Hot Tub | Downtown Ashland | Tesla Station

The Maple Apartment at Tudor House Vacation Rentals

9.6 out of 10, Exceptional, (138)
"Had a girls weekend. "
The Maple Apartment at Tudor House Vacation Rentals

Soda Mountain Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn

10.0 out of 10, Exceptional, (4)
"Beautiful quiet woods. An awesome cabin. Yahtzee and Scrabble "
The price is €383
includes taxes & fees
24 Nov - 25 Nov
Soda Mountain Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn

The Dogwood Suite at Tudor House Vacation Rentals

9.4 out of 10, Exceptional, (91)
"The property was exactly as described. Unit was clean, AC worked great. Courtyard was shaded and quiet and the property owner had no problem with us locking up our expensive bikes inside the yard instead of out at the bike rack. Will stay here again when visiting Ashland."
The Dogwood Suite at Tudor House Vacation Rentals
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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Other types of properties in Ashland you may be interested in

Stratford Inn

2.5 star property
9.2 out of 10, Wonderful, (1462)
"This hotel is older and has some charm. Very well maintained and CLEAN. (I was so relieved that it was surprisingly clean for an older hotel.) the pool was perfect. We really enjoyed our stay and will definitely be coming back. Our son is in college in the area and this place was just perfect. Quality at a good price is hard to find, Stratford Inn definitely is the best quality for the best price in the area. Next time we will bring our dog, now that we know it’s a great place for it. "
The price is €85
includes taxes & fees
2 Dec - 3 Dec
Stratford Inn

Ashland Hills Hotel & Suites

3.0 star property
9.0 out of 10, Wonderful, (1496)
"We enjoyed our stay quite a bit. We found the upgrade from the previous owner very appealing (a bit of a relief, frankly) and would definitely consider returning."
The price is €108
includes taxes & fees
1 Dec - 2 Dec
Ashland Hills Hotel & Suites

Ashland Springs Hotel

3.0 star property
9.4 out of 10, Exceptional, (1012)
"Absolutely amazing hotel. We had a perfect room that was quiet. Staff went above and beyond to ensure out stay was great. "
The price is €170
includes taxes & fees
25 Nov - 26 Nov
Ashland Springs Hotel
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.

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.

What are some of the best holiday rentals that Ashland has to offer?

Charming Retreat: Ashland's Urban Hideaway: This highly rated holiday home rental in Ashland offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of games. Some other homes for rent in Ashland include The Red Dragon House and Secluded Forest Log House 15 minutes to Ashland.

How many holiday rentals are there in Ashland?

Choose from 94 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.