Book Holiday Homes in Ashland

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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
Holiday Homes
Lowest Price
AU$143
Highest Price
AU$250
Popular accommodation
Stratford Inn, Ashland Hills Hotel & Suites, Callahan's Mountain Lodge, Ashland Springs Hotel

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$143 per night from 31 Dec to 1 Jan
AU$143
includes taxes & fees
31 Dec - 1 Jan 2025
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
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$174 per night from 30 Dec to 31 Dec
AU$174
includes taxes & fees
30 Dec - 31 Dec
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
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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$250 per night from 1 Jan to 2 Jan
AU$250
includes taxes & fees
1 Jan - 2 Jan 2025
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
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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.