Holiday Rentals in Jackson County

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Top Cities in Jackson County

Featured Holiday Rentals in Jackson County

Peach Street Inn by WanderLodges

2.0 star property
8.0 out of 10, Very good, (2)
"It was convenient and comfortable and clean, however the first thing we did after dropping our bags and getting situated,was attempt to make coffee. There was moldy coffee left in the filter, then we wondered if the ground coffee there was even useable. The area and people around this nice little place is concerning. We should have just stayed at the Rogue Regency instead. The extra property charge was not worth it."
The price is €151
includes taxes & fees
30 Nov - 1 Dec
Peach Street Inn by WanderLodges

Luxuriously comfortable & peaceful getaway downtown Ashland, with views.

10.0 out of 10, Exceptional, (8)
"My husband and I could not have been any happier to have stayed at Kathy's paradise! She was an incredibly responsive host and when we walked into this quaint little slice of heaven, it was just what we needed after hours of driving. The bed was very comfortable and I even took a bath in the beautful tub with heated floors in the bathroom! We wish we could have stayed longer and while traveling with two small dogs (one is my older service dog and the other is in training), she made us feel...
The price is €225
includes taxes & fees
3 Dec - 4 Dec
Luxuriously comfortable & peaceful getaway downtown Ashland, with views.

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 €490
includes taxes & fees
3 Dec - 4 Dec
Charming home, w/hot tub, close to 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

ZZ ZANY ZOO II - Townhome, with Carport & Garage

10.0 out of 10, Exceptional, (76)
"The place was clean and comfortable. Greeted with wine, cheese, fruit and snacks. The host Kathie went above and beyond. I will definitely stay there again. Highly recommend. "
ZZ ZANY ZOO II - Townhome, with Carport & Garage

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 €211
includes taxes & fees
2 Dec - 3 Dec
A Cowslip's Belle Inn

Charming Retreat: Ashland's Urban Hideaway

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...
Charming Retreat: Ashland's Urban Hideaway

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!

Tastefully remodeled 3 bedroom 2 bath home with large private back yard

10.0 out of 10, Exceptional, (31)
"Our stay was wonderful. The home fit our needs perfectly. Very well equipped with plentiful blankets, pillows,and comfortable seating. The kitchen had everything we needed. It was great having room to spread out either alone or in groups. We also loved the covered patio. We would definitely stay again. We would highly recommend. "
The price is €351
includes taxes & fees
9 Dec - 10 Dec
Tastefully remodeled 3 bedroom 2 bath home with large private back yard

Pet-Friendly Medford Vacation Rental w/ Yard!

9.2 out of 10, Wonderful, (7)
"Great cozy location"
Pet-Friendly Medford Vacation Rental w/ Yard!

New house with king beds and 3 full bathrooms

9.4 out of 10, Exceptional, (28)
"While this property had a few quirks, I really enjoyed this stay a lot. It was so nice to relax after a long day traveling."
The price is €240
includes taxes & fees
10 Dec - 11 Dec
New house with king beds and 3 full bathrooms

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

Comfy Cozy Casa

10.0 out of 10, Exceptional, (35)
"Came in town for a race event house was clean and organized."
The price is €281
includes taxes & fees
1 Dec - 2 Dec
Comfy Cozy Casa

Meadow House near Crater Lake South entrance, upper Rogue River, 100 acre trails

10.0 out of 10, Exceptional, (209)
"It was amazing. Such a great place and the owners were super friendly and helpful. Highly recommend to anyone wanting to stay in the area"
The price is €391
includes taxes & fees
1 Dec - 2 Dec
Meadow House near Crater Lake South entrance, upper Rogue River, 100 acre trails

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 €226
includes taxes & fees
2 Dec - 3 Dec
Courtside Cottage - WalkScore 93 - Dog Friendly

Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville

9.6 out of 10, Exceptional, (15)
"Wonderful stay at this cute cottage with my adult daughters. Owners were great and we enjoyed every minute of it. Can't wait to come back again. "
The price is €192
includes taxes & fees
1 Dec - 2 Dec
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville

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 €285
includes taxes & fees
5 Dec - 6 Dec
The Ashland Cottage, walk to town

Mid Century Modern Guest House

10.0 out of 10, Exceptional, (4)
"Really lovely home, super cozy for a couple and conveniently located. Definitely would stay again. "
The price is €171
includes taxes & fees
1 Dec - 2 Dec
Mid Century Modern Guest House

The Phoenix House- a place to relax and rejuvenate

8.8 out of 10, Excellent, (6)
"We have stayed there twice now. Our art gallery reception was last night in Medford. Today I visited a friend in Ashland. Debbie’s Diner is very close for breakfast and Starbucks down the road. The house has an elegant feel to it, high ceilings and lots of windows to the backyard. Thank you so much."
The price is €505
includes taxes & fees
29 Nov - 30 Nov
The Phoenix House- a place to relax and rejuvenate

Jacksonville Mountain Retreat

9.6 out of 10, Exceptional, (61)
"This is a very nice home. "
Jacksonville Mountain Retreat
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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