Book Holiday Homes in Southern Oregon

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Featured Holiday Homes in Southern Oregon

The River House. 5 miles from Crater Lake entrance.

The River House. 5 miles from Crater Lake entrance.

Fort Klamath
With a stay at this vacation home in Fort Klamath, you'll be on a river, within a 10-minute drive of Crater Lake National Park and Fort Klamath Park and ...
The River House. 5 miles from Crater Lake entrance.
Cedar Mountain - Suite E

Cedar Mountain - Suite E

Grants Pass
With a stay at this vacation home, you'll be centrally located in Grants Pass, just a 3-minute walk from Schmidt House Museum and 7 minutes by foot from Grants ...
Cedar Mountain - Suite E
Riverside Cabin 1 - (Brand New Construction)

Riverside Cabin 1 - (Brand New Construction)

Grants Pass
With a stay at this vacation home, you'll be centrally located in Grants Pass, just a 5-minute walk from Rogue River and 7 minutes by foot from Schmidt House ...
Riverside Cabin 1 - (Brand New Construction)
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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
Located in Chiloquin, this vacation home is within a 5-minute drive of Train Mountain Railroad Museum and Kla-Mo-Ya Casino.
Spacious Western Home on 2 acres in the Pines close to Crater Lake
Cedar Mountain - Suite D

Cedar Mountain - Suite D

Grants Pass
With a stay at this vacation home, you'll be centrally located in Grants Pass, just a 3-minute walk from Schmidt House Museum and 7 minutes by foot from Grants ...
Cedar Mountain - Suite D
1907 Charmer, Perfect Downtown Location, So Clean!

1907 Charmer, Perfect Downtown Location, So Clean!

Ashland
With a stay at this vacation home, you'll be centrally located in Ashland, within a 5-minute walk of Oregon Shakespeare Festival and Ashland Library.
1907 Charmer, Perfect Downtown Location, So Clean!
Jacksonville Place

Jacksonville Place

Medford
A stay at this vacation home places you in the heart of Medford, within a 5-minute drive of Blackbird Statue and Stewart Meadows Golf Course.
Jacksonville Place
Big Foot River Lodge

Big Foot River Lodge

Gold Hill
With a stay at this vacation home in Gold Hill, you'll be steps from Rogue River and a 3-minute drive from Valley of the Rogue State Park.
Big Foot River Lodge
The Green House - Minutes from the Entrance to Crater Lake National Park

The Green House - Minutes from the Entrance to Crater Lake National Park

Fort Klamath
Located in Fort Klamath, this vacation home is in a rural location, a 3-minute drive from Fort Klamath Park and Museum and 8 minutes from Jackson F Kimball State ...
The Green House - Minutes from the Entrance to Crater Lake National Park
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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.

Southern Oregon Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Southern Oregon vacation homes are the perfect way for you to wing it.

Holiday houses in Southern Oregon let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Southern Oregon in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Southern Oregon adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Southern Oregon with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Southern Oregon vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Top trending hotels in Southern Oregon

Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

3 out of 5
2300 Biddle Rd, Medford, OR
A stay at Rogue Regency Inn and Suites places you in the heart of Medford, a 3-minute drive from Providence Medford Medical Center and 5 minutes from The ...
Rogue Regency Inn and Suites
Cerulean Hotel

Cerulean Hotel

2.5 out of 5
100 Main St, Klamath Falls, OR
Fully refundableReserve now, pay when you stay
A stay at Cerulean Hotel places you in the heart of Klamath Falls, within a 5-minute walk of Veterans Memorial Park and Baldwin Hotel Museum.
Cerulean Hotel
Union Creek Resort

Union Creek Resort

3 out of 5
56484 Highway 62, Prospect, OR
With a stay at Union Creek Resort in Prospect, you'll be on a river, within a 15-minute drive of Crater Lake National Park and Rogue River-Siskiyou National ...
Union Creek Resort
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Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St, Ashland, OR
Fully refundableReserve now, pay when you stay
With a stay at Ashland Hills Hotel & Suites in Ashland, you'll be near ski lifts, within a 10-minute drive of Oregon Shakespeare Festival and Southern Oregon ...
Ashland Hills Hotel & Suites
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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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^Subject to availability and chosen travel dates.