Book Holiday Homes in Southern Oregon

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Southern Oregon

Railroad District, steps to downtown, everything you need to enjoy Ashland!

Railroad District, steps to downtown, everything you need to enjoy Ashland!

Ashland
With a stay at this vacation home, you'll be centrally located in Ashland, just a 5-minute walk from Ashland Library and 5 minutes by foot from Oregon Cabaret ...
Railroad District, steps to downtown, everything you need to enjoy Ashland!
Premier Downstairs Flat in Perfect Down Town Location

Premier Downstairs Flat in Perfect Down Town Location

Ashland
A stay at this vacation home places you in the heart of Ashland, steps from Ashland Library and 6 minutes by foot from Oregon Cabaret Theatre.
Premier Downstairs Flat in Perfect Down Town Location
Charming home, w/hot tub, close to downtown Pet-Friendly!

Charming home, w/hot tub, close to downtown Pet-Friendly!

Ashland
The price is AU$776 per night from 4 Jan to 5 Jan
AU$776
includes taxes & fees
4 Jan - 5 Jan 2025
Located in Ashland, this vacation home is within a 15-minute walk of Lithia Park and Allen Elizabethan Theatre.
Charming home, w/hot tub, close to downtown Pet-Friendly!
Save an average of 15% on thousands of hotels when you're signed in
The Rellik House and Winery

The Rellik House and Winery

3.5 out of 5
968 Old Stage Rd, Central Point, OR
The price is AU$539 per night from 8 Jan to 9 Jan
AU$539
includes taxes & fees
8 Jan - 9 Jan 2025
With a stay at The Rellik House and Winery in Central Point, you'll be steps from Caprice Vineyards and a 3-minute drive from Kharmic Creations.
The Rellik House and Winery
Pet-Friendly Medford Vacation Rental w/ Yard!

Pet-Friendly Medford Vacation Rental w/ Yard!

Medford
Located in Medford, this vacation home is a 4-minute drive from Providence Medford Medical Center and 6 minutes from Rogue Valley Mall.
Pet-Friendly Medford Vacation Rental w/ Yard!
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
The price is AU$548 per night from 9 Jan to 10 Jan
AU$548
includes taxes & fees
9 Jan - 10 Jan 2025
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
Jacksonville Mountain Retreat

Jacksonville Mountain Retreat

Jacksonville
With a stay at this vacation home in Jacksonville, you'll be within a 5-minute drive of Sarah Zigler Interpretive Trail and Kharmic Creations.
Jacksonville Mountain Retreat
The Phoenix House- a place to relax and rejuvenate

The Phoenix House- a place to relax and rejuvenate

Phoenix
Located in Phoenix, this vacation home is within a 5-minute drive of Phoenix Library and 2Hawk Vineyard & Winery.
The Phoenix House- a place to relax and rejuvenate
ZZ ZANY ZOO II -  Townhome, with Carport & Garage

ZZ ZANY ZOO II - Townhome, with Carport & Garage

Medford
With a stay at this vacation home, you'll be centrally located in Medford, within a 10-minute drive of Providence Medford Medical Center and Rogue Valley ...
ZZ ZANY ZOO II - Townhome, with Carport & Garage
Don't see what you're looking for?
See all available properties in Southern Oregon
View all properties
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.

Southern Oregon Holiday Homes essential information

Accommodation
420 Holiday Homes
Lowest Price
AU$143
Highest Price
AU$776
Popular accommodation
Railroad District, steps to downtown, everything you need to enjoy Ashland!, Premier Downstairs Flat in Perfect Down Town Location , Charming home, w/hot tub, close to downtown Pet-Friendly!, The Rellik House and Winery, Pet-Friendly Medford Vacation Rental w/ Yard!, Spacious Western Home on 2 acres in the Pines close to Crater Lake, Jacksonville Mountain Retreat, The Phoenix House- a place to relax and rejuvenate , ZZ ZANY ZOO II - Townhome, with Carport & Garage

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
Fully refundableReserve now, pay when you stay
The price is AU$175 per night from 8 Jan to 9 Jan
AU$175
includes taxes & fees
8 Jan - 9 Jan 2025
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
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is AU$143 per night from 30 Dec to 31 Dec
AU$143
includes taxes & fees
30 Dec - 31 Dec
Located in Ashland (Siskiyou-Hargadine Historic District), Stratford Inn is a 4-minute walk from Ashland Library and 9 minutes by foot from Oregon Cabaret ...
Stratford Inn
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is AU$167 per night from 5 Jan to 6 Jan
AU$167
includes taxes & fees
5 Jan - 6 Jan 2025
When you stay at Ashland Hills Hotel & Suites in Ashland, you'll be near ski lifts, within a 5-minute drive of Southern Oregon University and Weisinger Family ...
Ashland Hills Hotel & Suites
Save an average of 15% on thousands of hotels when you're signed in
Springhill Suites By Marriott Medford Airport

Springhill Suites By Marriott Medford Airport

3 out of 5
3519 HEATHROW WAY, Medford, OR
Fully refundableReserve now, pay when you stay
The price is AU$182 per night from 30 Dec to 31 Dec
AU$182
includes taxes & fees
30 Dec - 31 Dec
With a stay at Springhill Suites By Marriott Medford Airport in Medford, you'll be within a 5-minute drive of Rogue Valley Family Fun Center and Rogue Valley ...
Springhill Suites By Marriott Medford Airport
Don't see what you're looking for?
See all available properties in Southern Oregon
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.