Holiday Rentals in Ashland

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

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 €193
includes taxes & fees
6 Nov - 7 Nov
A Cowslip's Belle Inn
Premier Downstairs Flat in Perfect Down Town Location
10.0 out of 10, Exceptional, (46)
"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
Hyatt Lake Mountain Retreat
9.8 out of 10, Exceptional, (75)
"Thoroughly enjoyed our time"
Hyatt Lake Mountain Retreat
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
Mt Ashland Log Cabin w/Swedish sauna by Pacific Crest Trail-15 min from Ashland
10.0 out of 10, Exceptional, (49)
"We were welcomed into the log cabin that the owner built 30 years ago. It's a blend of beautiful carpentry with European and Japanese touches that wrap you in warmth and coziness. The cabin easily accommodated our group of 5 adults with the split bathroom design. It's very clean, with comfortable beds and bedding, different colored towels to easily keep track of your own, porch furnishings that extend the living area to the beautiful outdoors surrounding the cabin. Remote feeling yet a quick...
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 €191
includes taxes & fees
6 Dec - 7 Dec
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
Downtown Discovery: Explore Ashland's Charm
9.0 out of 10, Wonderful, (8)
"Studio B unit is in the back of property, where we enjoyed the privacy and window view to a quaint tree filled yard. We enjoyed the visit by 2 deer the 1st morning. The bed sheets were clean and soft on the comfortable king bed. Kitchen had all the amenities needed for our 4 day stay here in Ashland, would stay again!"
The price is €140
includes taxes & fees
6 Nov - 7 Nov
Downtown Discovery: Explore Ashland's Charm
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!
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 €416
includes taxes & fees
6 Nov - 7 Nov
Charming home, w/hot tub, close to downtown Pet-Friendly!
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 €276
includes taxes & fees
11 Nov - 12 Nov
The Ashland Cottage, walk to town
Ashland Escape: Downtown & Pet Friendly
9.8 out of 10, Exceptional, (26)
"Very comfortable, and we were thrilled with how close it was to all of our favorite shops and theaters. We were able to walk everywhere. Hope to stay again next year!"
The price is €303
includes taxes & fees
6 Nov - 7 Nov
Ashland Escape: Downtown & Pet Friendly
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 €390
includes taxes & fees
1 Dec - 2 Dec
Hyatt Praire Mountain Cabin
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!"
The price is €349
includes taxes & fees
2 Dec - 3 Dec
City Comfort: 3BDR Walkable Retreat
232-Duplex-Private Bathroom-Mountain View
10.0 out of 10, Exceptional, (34)
"I would shorten the code to get in."
232-Duplex-Private Bathroom-Mountain View
Courtside Cottage - WalkScore 93 - Dog Friendly
10.0 out of 10, Exceptional, (33)
"A clean cozy cottage perfectly located to enjoy Ashland."
The price is €217
includes taxes & fees
19 Nov - 20 Nov
Courtside Cottage - WalkScore 93 - Dog Friendly
The Maple Apartment at Tudor House Vacation Rentals
9.6 out of 10, Exceptional, (137)
"We loved this property. Comfy beds, very clean home with everything we needed. Host was very quick to respond to questions. Would definitely stay here again."
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)
"Amazingg "
The price is €369
includes taxes & fees
6 Nov - 7 Nov
Soda Mountain Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
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.
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.
Don't see what you're looking for?
See all available properties in Ashland
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Ashland you may be interested in

Stratford Inn
2.5 star property
9.2 out of 10, Wonderful, (1486)
"We had a very nice evening at the Stratford Inn and will be glad to stay there again. The front desk was very helpful, the room was spacious and clean and the hotel is close to downtown Ashland. The beds were very comfortable and everything about the room worked as required from the heat to the TV to the shower! It’s a great value in a wonderful town."
The price is €93
includes taxes & fees
6 Nov - 7 Nov
Stratford Inn
Ashland Hills Hotel & Suites
3.0 star property
9.0 out of 10, Wonderful, (1498)
"Very nice property in a very nice college town with a beautiful park nearby (Lithia park)"
The price is €127
includes taxes & fees
6 Nov - 7 Nov
Ashland Hills Hotel & Suites
Callahan's Mountain Lodge
3.0 star property
8.8 out of 10, Excellent, (1020)
"Cozy and comfortable! So much nicer than any chain hotel. Friendly staff, very clean, lots of amenities. I would definitely go back!"
The price is €105
includes taxes & fees
6 Nov - 7 Nov
Callahan's Mountain Lodge
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.