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
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
Out 'N' About Treehouse Treesort
2.5 star property
9.8 out of 10, Exceptional, (12)
"A bit run down than the last time I came but still such a great experience!"
United States
Alexa
The price is HK$1,026
HK$1,317 total
includes taxes & fees
2 Nov - 3 Nov
Out 'N' About Treehouse Treesort
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
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
Riverside Cabin 2 - (Brand New Construction)
10.0 out of 10, Exceptional, (102)
"Excellent place to stay! It was an adorable place with all the comforts of home."
United States
KoLynn P.
The price is HK$598
HK$1,047 total
includes taxes & fees
2 Nov - 3 Nov
Riverside Cabin 2 - (Brand New Construction)
Cozy Cottage Close to Crater Lake
9.2 out of 10, Wonderful, (80)
"We loved our stay at the cottage. The host has done a great job of thinking of little details that helped make the stay enjoyable."
United States
Amy S.
The price is HK$1,049
HK$1,727 total
includes taxes & fees
3 Nov - 4 Nov
Cozy Cottage Close to Crater Lake
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
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)
Modern New Studio with All Amenities!
10.0 out of 10, Exceptional, (38)
"One of the best stay we had!!! Everything was clean, convenient and arranged very well. If I get chance again, will revisit same accommodation again!!"
United States
Abhinith M.
The price is HK$552
HK$1,328 total
includes taxes & fees
2 Nov - 3 Nov
Modern New Studio with All Amenities!
Diggins Cabin 2 - Restrooms and Showers are only a short walk away.
9.6 out of 10, Exceptional, (8)
"The cabin was amazing and the bed was even better. Loved this place and will do a teepee next time."
United States
LeeD
The price is HK$595
HK$935 total
includes taxes & fees
2 Nov - 3 Nov
Diggins Cabin 2 - Restrooms and Showers are only a short walk away.
Serene Historic Cabin, Nine Acre Estate, Just Off I-5
9.8 out of 10, Exceptional, (41)
"It is a very unique property with good location and things you need!"
United States
Ivy D.
The price is HK$964
HK$1,420 total
includes taxes & fees
21 Nov - 22 Nov
Serene Historic Cabin, Nine Acre Estate, Just Off I-5
Reconnect with nature at this unforgettable escape
9.4 out of 10, Exceptional, (3)
"Clean and well equipped. Would stay again."
United States
Cheryl A.
The price is HK$802
HK$1,189 total
includes taxes & fees
2 Nov - 3 Nov
Reconnect with nature at this unforgettable escape
1930s Building on Main St Apt 211 Downtown
2.0 star property
9.6 out of 10, Exceptional, (4)
"This place was perfect for what we needed. We were looking for a place to stay overnight to break up a trip to crater lake. It’s a renovated older building and has some quirks but that’s part of the charm. "
United States
William J.
The price is HK$606
HK$1,319 total
includes taxes & fees
4 Nov - 5 Nov
1930s Building on Main St Apt 211 Downtown
Applegate Cabin 2 - Restrooms and Showers are only a short walk away.
9.0 out of 10, Wonderful, (4)
"Showers you need to pay for, don’t believe this was noted, also leaving cabins doors open all nite brings in many unwanted bugs and critters, my cabin was infested with ants, all over the Ugg throw they threw inside to make it look cozy. Maybe someone should have checked that out. Also spider webs all over the ceiling and windows. "
United States
Judy
The price is HK$595
HK$935 total
includes taxes & fees
2 Nov - 3 Nov
Applegate Cabin 2 - Restrooms and Showers are only a short walk away.
Rosie's Woodland Paradise! Come relax and rejuvenate!
10.0 out of 10, Exceptional, (129)
"Over the top amenities Paradise in woods "
United States
Scott and Sharon L.
The price is HK$777
HK$1,143 total
includes taxes & fees
3 Nov - 4 Nov
Rosie's Woodland Paradise! Come relax and rejuvenate!
The Vintage Cottage with riverfront access
9.8 out of 10, Exceptional, (109)
"What a beautiful location. The cottage was well equipped. We would stay here again."
United States
Victoria
The price is HK$769
HK$1,293 total
includes taxes & fees
2 Nov - 3 Nov
The Vintage Cottage with riverfront access
Luxury studio in the private hillside of Trail. Wi-Fi & Pet Friendly!
9.2 out of 10, Wonderful, (14)
"We enjoyed a quiet evening. Everything was kept tidy and was a good place for us to stop for the evening."
United States
Mary P.
The price is HK$660
HK$1,522 total
includes taxes & fees
2 Nov - 3 Nov
Luxury studio in the private hillside of Trail. Wi-Fi & Pet Friendly!
The Red Dragon House
10.0 out of 10, Exceptional, (102)
"Mike and Mindy's place had everything we could ask for and more."
United States
Carol C.
The price is HK$1,360
HK$1,561 total
includes taxes & fees
19 Nov - 20 Nov
The Red Dragon House
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
10.0 out of 10, Exceptional, (18)
"Nice place. Very clean and well appointed. Close to town, but still on a farm that makes it seem far away. We'd come back."
United States
Dan W.
The price is HK$614
HK$1,388 total
includes taxes & fees
16 Nov - 17 Nov
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
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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