Book Holiday Homes in Southern Oregon

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Featured Holiday Homes in Southern Oregon

Premier Downstairs Flat in Perfect Down Town Location

Premier Downstairs Flat in Perfect Down Town Location

Ashland OR
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.
Opens in a new windowPremier Downstairs Flat in Perfect Down Town Location
The River House with Views of the Famous Rogue River! No cleaning fees!

The River House with Views of the Famous Rogue River! No cleaning fees!

Grants Pass OR
The price is AU$265 per night from 15 Mar to 16 Mar
AU$265
15 Mar - 16 Mar
includes taxes & fees
Located in Grants Pass, this vacation home is on a river, a 1-minute drive from Rogue River and 8 minutes from Riverside Park.
Opens in a new windowThe River House with Views of the Famous Rogue River! No cleaning fees!
Tilty House in the Hidden Hills

Tilty House in the Hidden Hills

Klamath Falls OR
With a stay at this vacation home in Klamath Falls (Downtown Klamath Falls), you'll be within a 5-minute drive of Oregon Institute of Technology - Residential ...
Opens in a new windowTilty House in the Hidden Hills
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Beautiful bungalow downtown Ashland railroad district

Beautiful bungalow downtown Ashland railroad district

2 out of 5
Ashland OR
Located in Ashland, this vacation home is within a 15-minute walk of Ashland Creek and Lithia Park.
Opens in a new windowBeautiful bungalow downtown Ashland railroad district
New Downtown 3 Bedroom Upstairs Flat with views

New Downtown 3 Bedroom Upstairs Flat with views

Ashland OR
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.
Opens in a new windowNew Downtown 3 Bedroom Upstairs Flat with views
Riverside Cabin 5 - (Brand New Construction)

Riverside Cabin 5 - (Brand New Construction)

Grants Pass OR
The price is AU$210 per night from 17 Mar to 18 Mar
AU$210
17 Mar - 18 Mar
includes taxes & fees
With a stay at this vacation home in Grants Pass, you'll be a 5-minute walk from Rogue River and 7 minutes by foot from Schmidt House Museum.
Opens in a new windowRiverside Cabin 5 - (Brand New Construction)
Award Winning Britt Bungalow in the Historical Heart of Jacksonville Oregon

Award Winning Britt Bungalow in the Historical Heart of Jacksonville Oregon

Jacksonville OR
The price is AU$456 per night from 9 Mar to 10 Mar
AU$456
9 Mar - 10 Mar
includes taxes & fees
With a stay at this vacation home in Jacksonville (Jacksonville Historic District), you'll be within a 5-minute walk of Sarah Zigler Interpretive Trail and Jacksonville ...
Opens in a new windowAward Winning Britt Bungalow in the Historical Heart of Jacksonville Oregon
Jacksonville Place

Jacksonville Place

Medford OR
The price is AU$296 per night from 9 Mar to 10 Mar
AU$296
9 Mar - 10 Mar
includes taxes & fees
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.
Opens in a new windowJacksonville Place
East Main Downtown Bungalow

East Main Downtown Bungalow

Ashland OR
The price is AU$309 per night from 8 Mar to 9 Mar
AU$309
8 Mar - 9 Mar
includes taxes & fees
With a stay at this vacation home in Ashland (Historic Railroad District), you'll be steps from Ashland Library and 6 minutes by foot from Oregon Cabaret ...
Opens in a new windowEast Main Downtown Bungalow
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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.

Southern Oregon Holiday Homes essential information

Accommodation
455 Holiday Homes
Lowest Price
AU$171
Highest Price
AU$456
Popular accommodation
Premier Downstairs Flat in Perfect Down Town Location , The River House with Views of the Famous Rogue River! No cleaning fees!, Tilty House in the Hidden Hills, Beautiful bungalow downtown Ashland railroad district, New Downtown 3 Bedroom Upstairs Flat with views, Riverside Cabin 5 - (Brand New Construction), Award Winning Britt Bungalow in the Historical Heart of Jacksonville Oregon, Jacksonville Place, East Main Downtown Bungalow

Top trending hotels in Southern Oregon

Rogue Regency Inn Medford Airport

Rogue Regency Inn Medford Airport

3 out of 5
2300 Biddle Rd Medford OR
Fully refundableReserve now, pay when you stay
A stay at Rogue Regency Inn Medford Airport places you in the heart of Medford, a 3-minute drive from Providence Medford Medical Center and 5 minutes from The ...
Opens in a new windowRogue Regency Inn Medford Airport
Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St Ashland OR
Fully refundableReserve now, pay when you stay
The price is AU$171 per night from 11 Mar to 12 Mar
AU$171
11 Mar - 12 Mar
includes taxes & fees
A stay at Ashland Springs Hotel places you in the heart of Ashland, steps from Oregon Cabaret Theatre and Allen Elizabethan Theatre.
Opens in a new windowAshland Springs Hotel
Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
2399 S Pacific Hwy Medford OR
Fully refundableReserve now, pay when you stay
The price is AU$229 per night from 8 Mar to 9 Mar
AU$229
8 Mar - 9 Mar
includes taxes & fees
When you stay at Compass by Margaritaville in Medford in Medford, you'll be next to a golf course, within a 5-minute drive of Lithia & Driveway Fields and Southern ...
Opens in a new windowCompass by Margaritaville in Medford
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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
The price is AU$171 per night from 8 Mar to 9 Mar
AU$171
8 Mar - 9 Mar
includes taxes & fees
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 ...
Opens in a new windowAshland 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.