Southern Oregon Holiday Rentals

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Holiday Rentals in Southern Oregon

Crater Lake Resort
3.0 star property
8.4 out of 10, Very good, (514)
"Beautiful area"
United States
Jann
Crater Lake Resort
Union Creek Resort
3.0 star property
8.0 out of 10, Very good, (907)
"Beautiful location near Crater Lake. Lots of short scenic hikes nearby. "
United States
karen
Union Creek Resort
Rocky Point Resort
2.5 star property
8.2 out of 10, Very good, (395)
"We really enjoyed our stay at Rocky Point. The room was comfortable and the area is beautiful. "
United States
Franci
The price is HK$664
HK$754 total
includes taxes & fees
9 Nov - 10 Nov
Rocky Point Resort
Peach Street Inn by WanderLodges
2.0 star property
9.2 out of 10, Wonderful, (27)
"Very nice property and rooms are spacious and clean. Will definitely return,"
United States
Nancy
Peach Street Inn by WanderLodges
Jacksonville Place
9.0 out of 10, Wonderful, (28)
"It was a nice quiet place, wish I could’ve stayed longer. "
United States
steven
The price is HK$888
HK$1,480 total
includes taxes & fees
2 Nov - 3 Nov
Jacksonville Place
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
9.8 out of 10, Exceptional, (100)
"This is a really great spot to stay. I was attending a wedding in Central pPoint. Lots of wineries close by, hiking trails, and of course you can get into town pretty easily. Beautiful spots to enjoy the river are within minutes. There’s even a couple stores and restaurants that you can walk to. I would definitely stay here again."
United States
Michelle H.
The price is HK$761
HK$1,372 total
includes taxes & fees
3 Nov - 4 Nov
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
Harriman Springs Resort Cabin 2 - Cabins with a View
9.0 out of 10, Wonderful, (134)
"This cabin is a gem in the middle of a mountain forest!!!"
United States
STEIN H.
The price is HK$1,049
HK$1,319 total
includes taxes & fees
2 Nov - 3 Nov
Harriman Springs Resort Cabin 2 - Cabins with a View
A Cowslip's Belle Inn
3.0 star property
9.8 out of 10, Exceptional, (39)
"The place was great!!"
United States
Gianna
The price is HK$1,049
HK$1,603 total
includes taxes & fees
16 Nov - 17 Nov
A Cowslip's Belle Inn
Paschal Winery
4.5 star property
9.6 out of 10, Exceptional, (13)
"It is a beautiful property. We stayed in the little trailer, glamp cottage and it was so cute. Also enjoyed the private hot tub provided. We did some wine tasting, a flight of white and a flight of reds and enjoyed their fabulous cork and fork dinner. The location is beautiful. My travelling companion said if she didn’t know better she would think she was in Switzerland."
United States
Heidi
The price is HK$611
HK$1,359 total
includes taxes & fees
9 Nov - 10 Nov
Paschal Winery
Harriman Springs Resort Cabin 3 - Cabins with a View
9.2 out of 10, Wonderful, (170)
"What a beautiful cabin! The craftmanship is absolutely beautiful. The little touches of which there are many, make a huge positive impression. Cant wait to come back!"
United States
Lauri V.
The price is HK$1,049
HK$1,319 total
includes taxes & fees
2 Nov - 3 Nov
Harriman Springs Resort Cabin 3 - Cabins with a View
Courtside Cottage - WalkScore 93 - Dog Friendly
10.0 out of 10, Exceptional, (58)
"The place is exactly as pictured and extremely comfortable. It is such a great neighborhood with easy walks to restaurants and plays. "
United States
Kim C.
The price is HK$959
HK$1,944 total
includes taxes & fees
9 Nov - 10 Nov
Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
9.8 out of 10, Exceptional, (58)
"Michael’s place was great! A short walk to many things and enough room for lots of family. "
United States
Emily Y.
The price is HK$1,364
HK$3,721 total
includes taxes & fees
3 Nov - 4 Nov
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
Luxuriously comfortable & peaceful getaway downtown Ashland, with views.
10.0 out of 10, Exceptional, (32)
"This is the second time I’ve stayed here and I just LOVE it! You have everything needed for a relaxing break—the outside seating areas and the huge soaking tub make it extra special. Also so close to the downtown area and theater options. "
United States
Julie G.
The price is HK$769
HK$1,464 total
includes taxes & fees
2 Nov - 3 Nov
Luxuriously comfortable & peaceful getaway downtown Ashland, with views.
The 777 House
10.0 out of 10, Exceptional, (62)
"Very comfortable house to stay while visiting family"
United States
Nikki K.
The price is HK$902
HK$2,336 total
includes taxes & fees
3 Nov - 4 Nov
The 777 House
Sunshine Studio - Private apt and yard (eco, solar)
10.0 out of 10, Exceptional, (86)
"Incredibly inviting, clean, thoughtful cultivation of the space. Would absolutely stay again and also recommend! "
United States
Dakotah S.
The price is HK$777
HK$1,049 total
includes taxes & fees
2 Nov - 3 Nov
Sunshine Studio - Private apt and yard (eco, solar)
Spacious Western Home on 2 acres in the Pines close to Crater Lake
10.0 out of 10, Exceptional, (127)
"Communication was incredible. I would absolutely recommend this property to anyone. It is an absolutely beautiful house. "
United States
Matthew
The price is HK$1,049
HK$2,484 total
includes taxes & fees
2 Nov - 3 Nov
Spacious Western Home on 2 acres in the Pines close to Crater Lake
The Rellik House and Winery
3.5 star property
9.4 out of 10, Exceptional, (3)
"Beautiful property on the winery. Nicely decorated room & large shower. Separate living, kitchenette & bedroom area. The only downside is the room we had had the parking area on one side & the winery tasting room on the other. So we kept our curtains closed. Also the hot tub was dirty. We were looking forward to using it. "
United States
Laurel
The price is HK$1,140
HK$1,895 total
includes taxes & fees
1 Dec - 2 Dec
The Rellik House and Winery
Lovely Riverfront Grants Pass Home: Pool & Hot Tub
10.0 out of 10, Exceptional, (2)
"The best VRBO I have ever stayed in. I cannot wait to come back- this place has everything! Some core memories made in this beautiful an and idyllic place. 10 stars, hands down"
United States
Katie C.
Lovely Riverfront Grants Pass Home: Pool & Hot Tub
SERENE LAKEFRONT ESCAPE WITH PRIVATE BOAT RAMP AND LAKE & MOUNTAIN VIEWS
9.4 out of 10, Exceptional, (21)
"We had a wonderful time!"
United States
Carolyn C.
The price is HK$1,942
HK$4,347 total
includes taxes & fees
17 Nov - 18 Nov
SERENE LAKEFRONT ESCAPE WITH PRIVATE BOAT RAMP AND LAKE & MOUNTAIN VIEWS
Red Blanket Cabin Near Crater Lake National Park
10.0 out of 10, Exceptional, (391)
"If I were in this area again I would definitely stay here again. Very well stocked and very clean. Love all the hiking and waterfalls nearby!"
United States
Lynda
Red Blanket Cabin Near Crater Lake National Park
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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