Book Holiday Homes in Ashland

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Featured Holiday Homes in Ashland

ZZ ZANY ZOO II -  Townhome, with Carport & Garage

ZZ ZANY ZOO II - Townhome, with Carport & Garage

Medford
Book a stay at this family-friendly vacation home in Medford. Enjoy free WiFi, a water park, and a garden. Popular attractions Medford Railroad Park and Rogue ...
ZZ ZANY ZOO II - Townhome, with Carport & Garage
Quiet and peaceful cottage close to downtown

Quiet and peaceful cottage close to downtown

Ashland
The price is NZ$580 per night from 6 Apr to 7 Apr
NZ$580
includes taxes & fees
6 Apr - 7 Apr
Stay at this vacation home in Ashland. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Ashland Library and Oregon Cabaret ...
Quiet and peaceful cottage close to downtown
New house with king beds and 3 full bathrooms

New house with king beds and 3 full bathrooms

Medford
The price is NZ$503 per night from 6 Apr to 7 Apr
NZ$503
includes taxes & fees
6 Apr - 7 Apr
Book a stay at this golf vacation home in Medford. Enjoy free WiFi, a garden, and patios. Popular attractions Medford Railroad Park and Rogue Valley Mall are ...
New house with king beds and 3 full bathrooms
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Charming home, w/hot tub, close to downtown Pet-Friendly!

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

Ashland
The price is NZ$1,061 per night from 7 Apr to 8 Apr
NZ$1,061
includes taxes & fees
7 Apr - 8 Apr
Book a stay at this family-friendly vacation home in Ashland. Enjoy free WiFi, a garden, and patios. Popular attractions Allen Elizabethan Theatre and Angus ...
Charming home, w/hot tub, close to downtown Pet-Friendly!
The Original ZZ ZANY ZOO Townhome, with Carport & Garage 
 #1

The Original ZZ ZANY ZOO Townhome, with Carport & Garage #1

Medford
Book a stay at this family-friendly vacation home in Medford. Enjoy free WiFi, a water park, and a garden. Popular attractions Medford Railroad Park and Rogue ...
The Original ZZ ZANY ZOO Townhome, with Carport & Garage #1
Tastefully remodeled 3 bedroom 2 bath home with large private back yard

Tastefully remodeled 3 bedroom 2 bath home with large private back yard

Medford
The price is NZ$688 per night from 6 Apr to 7 Apr
NZ$688
includes taxes & fees
6 Apr - 7 Apr
Stay at this vacation home in Medford. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Rocky Knoll Tasting Room and Rogue Valley Country ...
Tastefully remodeled 3 bedroom 2 bath home with large private back yard
Large Private Carriage-House Retreat with Amazing Views

Large Private Carriage-House Retreat with Amazing Views

Medford
Stay at this vacation home in Medford. Enjoy free WiFi, a garden, and patios. Popular attractions RoxyAnn Winery and Rocky Knoll Tasting Room are located ...
Large Private Carriage-House Retreat with Amazing Views
Great, clean house in the middle of Medford

Great, clean house in the middle of Medford

Medford
The price is NZ$564 per night from 6 Apr to 7 Apr
NZ$564
includes taxes & fees
6 Apr - 7 Apr
Stay at this vacation home in Medford. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Rocky Knoll Tasting Room and Rogue Valley ...
Great, clean house in the middle of Medford
Cedar Wood Mountain View Retreat

Cedar Wood Mountain View Retreat

Ashland
Book a stay at this family-friendly vacation home in Ashland. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Allen Elizabethan Theatre ...
Cedar Wood Mountain View Retreat
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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.

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
285 Holiday Homes
Lowest Price
NZ$231
Highest Price
NZ$1,061
Popular accommodation
ZZ ZANY ZOO II - Townhome, with Carport & Garage , Quiet and peaceful cottage close to downtown, New house with king beds and 3 full bathrooms, Charming home, w/hot tub, close to downtown Pet-Friendly!, The Original ZZ ZANY ZOO Townhome, with Carport & Garage #1, Tastefully remodeled 3 bedroom 2 bath home with large private back yard, Large Private Carriage-House Retreat with Amazing Views, Great, clean house in the middle of Medford, Cedar Wood Mountain View Retreat

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 NZ$231 per night from 17 Apr to 18 Apr
NZ$231
includes taxes & fees
17 Apr - 18 Apr
Book a stay at this business-friendly hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the pool ...
Stratford Inn
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 NZ$293 per night from 6 Apr to 7 Apr
NZ$293
includes taxes & fees
6 Apr - 7 Apr
Stay at this 3-star spa hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Ashland Springs Hotel
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 NZ$241 per night from 5 May to 6 May
NZ$241
includes taxes & fees
5 May - 6 May
Stay at this 3-star ski hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in ...
Ashland Hills Hotel & Suites
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Plaza Inn & Suites at Ashland Creek

Plaza Inn & Suites at Ashland Creek

3 out of 5
98 Central Ave, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is NZ$272 per night from 6 Apr to 7 Apr
NZ$272
includes taxes & fees
6 Apr - 7 Apr
Stay at this 3-star business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Plaza Inn & Suites at Ashland Creek
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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.