A town nestled in a valley with a prominent building in the foreground and hills in the background.

Southern Oregon Holiday Rentals

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Our top choices for Southern Oregon holiday rentals

1. Rocky Point Resort

Rocky Point Resort
2.5 star property
Klamath Falls
8.2 out of 10, Very good, (476 reviews)
"Great location."
United States
Noni
The price is NZ$163
includes taxes & fees
9 Sept - 10 Sept
Rocky Point Resort

2. Union Creek Resort

Union Creek Resort
3.0 star property
Prospect
8.0 out of 10, Very good, (1,033 reviews)
"Very accommodating & friendly staff."
United States
Dave
The price is NZ$250
includes taxes & fees
29 Sept - 30 Sept
Union Creek Resort

3. Spacious Western Home on 2 acres in the Pines close to Crater Lake

Spacious Western Home on 2 acres in the Pines close to Crater Lake
Chiloquin
10.0 out of 10, Exceptional, (143 reviews)
"Beautiful home in Chiloquin. Spacious, clean, well stocked and very homey"
United States
Debbie
The price is NZ$606
includes taxes & fees
30 Aug - 31 Aug
Spacious Western Home on 2 acres in the Pines close to Crater Lake

4. Cozy Cottage Close to Crater Lake

Cozy Cottage Close to Crater Lake
Fort Klamath
9.2 out of 10, Wonderful, (97 reviews)
"Great location and very comfortable."
United States
Jonathan K.
The price is NZ$376
includes taxes & fees
31 Aug - 1 Sept
Cozy Cottage Close to Crater Lake

5. The 'Easy A' Cabin at Rocky Point- Stylish 1960's A-Frame

The 'Easy A' Cabin at Rocky Point- Stylish 1960's A-Frame
Klamath Falls
9.8 out of 10, Exceptional, (43 reviews)
"Perfect for a cozy get away! We stayed 5 nights in the Easy A and couldn’t be happier with how it was set up. Everything was very well explained, amenities and cleanliness very well thought out. Definitely would stay here again"
United States
Madison W.
The price is NZ$428
includes taxes & fees
7 Sept - 8 Sept
The 'Easy A' Cabin at Rocky Point- Stylish 1960's A-Frame

6. The Historic George Hotel

The Historic George Hotel
3.5 star property
Downtown Klamath Falls
7.8 out of 10, Good, (11 reviews)
"Beautiful, Amazing, Wonderful ."
United States
Kristin
The price is NZ$246
includes taxes & fees
7 Sept - 8 Sept
The Historic George Hotel

7. Paschal Winery

Paschal Winery
4.5 star property
Talent
9.8 out of 10, Exceptional, (19 reviews)
"Stunning scenery, great wine and food. Friendly, helpful people on site and the hot tub is blissfully perfect ❤️"
United States
Christine
The price is NZ$692
includes taxes & fees
10 Sept - 11 Sept
Paschal Winery

8. Out 'N' About Treehouse Treesort

Out 'N' About Treehouse Treesort
2.5 star property
Cave Junction
9.4 out of 10, Exceptional, (32 reviews)
"Nice unique place to stay. Kitchen setup is great with all utensils and facilities, good entertainments"
United States
ravendran
The price is NZ$402
includes taxes & fees
8 Sept - 9 Sept
Out 'N' About Treehouse Treesort

9. Tilty House in the Hidden Hills

Tilty House in the Hidden Hills
Downtown Klamath Falls
9.6 out of 10, Exceptional, (16 reviews)
"Everything was great. Will stay again."
United States
Richard S.
The price is NZ$344
includes taxes & fees
29 Sept - 30 Sept
Tilty House in the Hidden Hills

10. Basecamp GP Private Unit in Quiet Duplex

Basecamp GP Private Unit in Quiet Duplex
3.5 star property
Grants Pass
10.0 out of 10, Exceptional, (1 review)
The price is NZ$337
includes taxes & fees
7 Sept - 8 Sept
Basecamp GP Private Unit in Quiet Duplex

11. Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (9 reviews)
"The Grandview house and property far exceeded our expectations. We especially enjoying making meals together in the beautiful kitchen and reminiscing on the deck while taking in the spectacular views. We were fortunate to see lots of wildlife too. We hope to come back next year."
United States
Sonja
The price is NZ$663
includes taxes & fees
14 Sept - 15 Sept
Grandview of Ashland

12. Starwood Sanctuary

Starwood Sanctuary
3.0 star property
Medford
9.4 out of 10, Exceptional, (3 reviews)
"I was able to have early check in. The private bathroom off the main room was tiny. Coffee and cocoa were nice. The beds were comfy but the accent lights didn’t work and the shampoo dispenser was broken. Price and location were nice.. may book again.. spider webs outside 🤔😊"
United States
Erin
The price is NZ$468
includes taxes & fees
8 Sept - 9 Sept
Starwood Sanctuary

13. Modern New Studio with All Amenities!

Modern New Studio with All Amenities!
Klamath Falls
10.0 out of 10, Exceptional, (52 reviews)
"Lovely place to stay. Very relaxing and safe."
United States
Julie W.
The price is NZ$307
includes taxes & fees
1 Sept - 2 Sept
Modern New Studio with All Amenities!

14. Redwoods Stopover by WanderLodges

Redwoods Stopover by WanderLodges
2.0 star property
Cave Junction
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home. My truck didn’t fit in the garage but there’s a gate that I was able to park it behind. Support staff were super helpful."
United States
Braden
The price is NZ$441
includes taxes & fees
30 Aug - 31 Aug
Redwoods Stopover by WanderLodges

15. Sunshine Studio - Private apt and yard (eco, solar)

Sunshine Studio - Private apt and yard (eco, solar)
MEDFORD
10.0 out of 10, Exceptional, (107 reviews)
"Sunshine Studio was a very clean, cozy, and private place to stay while we were visiting the Medford area."
United States
Lynn F.
The price is NZ$236
includes taxes & fees
30 Aug - 31 Aug
Sunshine Studio - Private apt and yard (eco, solar)

16. Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub

Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
Central Point
9.8 out of 10, Exceptional, (126 reviews)
"We had such an amazing relaxing weekend at this little hidden jewel, tucked away in Central Point. "
United States
Chris A.
The price is NZ$299
includes taxes & fees
30 Aug - 31 Aug
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub

17. Luxury studio in the private hillside of Trail. Wi-Fi & Pet Friendly!

Luxury studio in the private hillside of Trail. Wi-Fi & Pet Friendly!
Trail
9.0 out of 10, Wonderful, (18 reviews)
"Cozy spot, clean and quiet. Cute place!"
United States
Cassandra R.
The price is NZ$347
includes taxes & fees
8 Sept - 9 Sept
Luxury studio in the private hillside of Trail. Wi-Fi & Pet Friendly!

18. Diggins Cabin 2 - Restrooms and Showers are only a short walk away.

Diggins Cabin 2 - Restrooms and Showers are only a short walk away.
O'Brien
9.6 out of 10, Exceptional, (9 reviews)
"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 NZ$212
includes taxes & fees
30 Aug - 31 Aug
Diggins Cabin 2 - Restrooms and Showers are only a short walk away.
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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Top Southern Oregon Hotel Reviews

Find out more about Southern Oregon

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Southern Oregon holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Southern Oregon. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Southern Oregon. Seeing all the best attractions is bound to make you fall in love with Southern Oregon. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Southern Oregon short-term rentals, that won’t be hard to do.

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