Book Holiday Homes in Ashland

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 Ashland

Southern Oregon Gem (EV Charger)

Southern Oregon Gem (EV Charger)

Medford
The price is AU$262 per night from 26 Nov to 27 Nov
AU$262
includes taxes & fees
26 Nov - 27 Nov
With a stay at this vacation home in Medford (City Center Medford), you'll be within a 10-minute walk of Southern Oregon University Medford Campus and Bear Creek ...
Southern Oregon Gem (EV Charger)
Comfy Cozy Casa

Comfy Cozy Casa

Medford
The price is AU$460 per night from 10 Dec to 11 Dec
AU$460
includes taxes & fees
10 Dec - 11 Dec
A stay at this vacation home places you in the heart of Medford, a 4-minute drive from Providence Medford Medical Center and 5 minutes from Rogue Valley ...
Comfy Cozy Casa
Harriman Springs Resort Cabin 1 - A Vacation House with Accommodations & Views

Harriman Springs Resort Cabin 1 - A Vacation House with Accommodations & Views

Klamath Falls
When you stay at this vacation home in Klamath Falls, you'll be on the waterfront, within a 5-minute drive of Upper Klamath National Wildlife Refuge and Upper ...
Harriman Springs Resort Cabin 1 - A Vacation House with Accommodations & Views
Save an average of 15% on thousands of hotels when you're signed in
Rogue Valley Retreat in Medford, OR

Rogue Valley Retreat in Medford, OR

Medford
A stay at this vacation home places you in the heart of Medford, within a 5-minute drive of Fichtner-Mainwaring Park and DANCIN Vineyards.
Rogue Valley Retreat in Medford, OR
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$784 per night from 3 Dec to 4 Dec
AU$784
includes taxes & fees
3 Dec - 4 Dec
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!
Renovated Home in Central Point

Renovated Home in Central Point

Central Point
With a stay at this vacation home in Central Point, you'll be within a 15-minute walk of Rogue Creamery and Lillie Belle Farms.
Renovated Home in Central Point
The Phoenix House- a place to relax and rejuvenate

The Phoenix House- a place to relax and rejuvenate

Phoenix
The price is AU$803 per night from 29 Nov to 30 Nov
AU$803
includes taxes & fees
29 Nov - 30 Nov
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
Station House Suite A

Station House Suite A

Jacksonville
The price is AU$812 per night from 30 Nov to 1 Dec
AU$812
includes taxes & fees
30 Nov - 1 Dec
With a stay at this vacation home in Jacksonville, you'll be just steps from Kharmic Creations and Art Presence Art Center.
Station House Suite A
Cheerful 3-Bedroom home in Central Point

Cheerful 3-Bedroom home in Central Point

Central Point
A stay at this vacation home places you in the heart of Central Point, within a 5-minute drive of Lillie Belle Farms and Rogue Creamery.
Cheerful 3-Bedroom home in Central Point
Don't see what you're looking for?
See all available properties in Ashland
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.

Ashland 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 Ashland vacation homes are the perfect way for you to wing it.

Holiday houses in Ashland 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 Ashland 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 Ashland adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Ashland 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 Ashland 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.

Ashland Holiday Homes essential information

Accommodation
235 Holiday Homes
Lowest Price
AU$137
Highest Price
AU$812
Popular accommodation
Southern Oregon Gem (EV Charger), Comfy Cozy Casa, Harriman Springs Resort Cabin 1 - A Vacation House with Accommodations & Views, Rogue Valley Retreat in Medford, OR, Charming home, w/hot tub, close to downtown Pet-Friendly!, Renovated Home in Central Point, The Phoenix House- a place to relax and rejuvenate , Station House Suite A, Cheerful 3-Bedroom home in Central Point

Top trending hotels in Ashland

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$137 per night from 2 Dec to 3 Dec
AU$137
includes taxes & fees
2 Dec - 3 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$176 per night from 1 Dec to 2 Dec
AU$176
includes taxes & fees
1 Dec - 2 Dec
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
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$274 per night from 1 Dec to 2 Dec
AU$274
includes taxes & fees
1 Dec - 2 Dec
A stay at Ashland Springs Hotel places you in the heart of Ashland, steps from Oregon Cabaret Theatre and Allen Elizabethan Theatre.
Ashland Springs Hotel
Save an average of 15% on thousands of hotels when you're signed in
Callahan's Mountain Lodge

Callahan's Mountain Lodge

3 out of 5
7100 Old Highway 99 South, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is AU$137 per night from 26 Nov to 27 Nov
AU$137
includes taxes & fees
26 Nov - 27 Nov
Located in Ashland, Callahan's Mountain Lodge is in the mountains, within a 15-minute drive of Emigrant Lake and Southern Oregon University.
Callahan's Mountain Lodge
Don't see what you're looking for?
See all available properties in Ashland
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.