Book Holiday Homes in Enterprise

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 Enterprise

Craftsman House-Near Downtown & Dog Friendly

Craftsman House-Near Downtown & Dog Friendly

Walla Walla
With a stay at this vacation home in Walla Walla, you'll be within a 5-minute drive of Whitman College and Jumpin' Jellybeanz.
Craftsman House-Near Downtown & Dog Friendly
Beautiful lakefront house with private boat dock, washer/dryer & fireplace

Beautiful lakefront house with private boat dock, washer/dryer & fireplace

Joseph
With a stay at this vacation home, you'll be centrally located in Joseph, within a 5-minute drive of Wallowa Lake and Wallowa River.
Beautiful lakefront house with private boat dock, washer/dryer & fireplace
Urban Oasis in Downtown Walla Walla.  Walk to Wine, Restaurants and More!

Urban Oasis in Downtown Walla Walla. Walk to Wine, Restaurants and More!

Walla Walla
A stay at this vacation home places you in the heart of Walla Walla, steps from Gesa Power House Theatre and 3 minutes by foot from Downtown Farmers Market.
Urban Oasis in Downtown Walla Walla. Walk to Wine, Restaurants and More!
Save an average of 15% on thousands of hotels when you're signed in
Francis House · Francis House a Bungalow - Close to Everything

Francis House · Francis House a Bungalow - Close to Everything

Walla Walla
With a stay at this vacation home in Walla Walla, you'll be within a 15-minute walk of Whitman College and Pioneer Park Aviary.
Francis House · Francis House a Bungalow - Close to Everything
Cheerful And Spacious Home For Lovers Of Good Food And Wine

Cheerful And Spacious Home For Lovers Of Good Food And Wine

Walla Walla
A stay at this vacation home places you in the heart of Walla Walla, within a 5-minute drive of Whitman College and Downtown Farmers Market.
Cheerful And Spacious Home For Lovers Of Good Food And Wine
Stay at the Historical Cropp Mansion

Stay at the Historical Cropp Mansion

Walla Walla
A stay at this vacation home places you in the heart of Walla Walla, steps from Whitman College and 7 minutes by foot from Kirkman House Museum.
Stay at the Historical Cropp Mansion
Charming riverfront home with fireplace, patio, grill, & full kitchen

Charming riverfront home with fireplace, patio, grill, & full kitchen

Joseph
When you stay at this vacation home in Joseph, you'll be on the waterfront, within a 15-minute walk of Wallowa Lake and Wallowa River.
Charming riverfront home with fireplace, patio, grill, & full kitchen
Sodo Landing

Sodo Landing

Walla Walla
A stay at this vacation home places you in the heart of Walla Walla, within a 10-minute walk of Providence St. Mary Medical Center - Walla Walla and Jumpin' ...
Sodo Landing
Moonrise Suite in a Vineyard + Winery!

Moonrise Suite in a Vineyard + Winery!

Milton-Freewater
Located in Milton-Freewater, this farm stay is on a river, within a 15-minute drive of Frazier Farmstead Museum and Old City Cemetery.
Moonrise Suite in a Vineyard + Winery!
Don't see what you're looking for?
See all available properties in Enterprise
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.

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

Holiday houses in Enterprise 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 Enterprise 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 Enterprise adventures, obvs.

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

Enterprise Holiday Homes essential information

Accommodation
188 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Craftsman House-Near Downtown & Dog Friendly, Beautiful lakefront house with private boat dock, washer/dryer & fireplace, Urban Oasis in Downtown Walla Walla. Walk to Wine, Restaurants and More!, Francis House · Francis House a Bungalow - Close to Everything, Cheerful And Spacious Home For Lovers Of Good Food And Wine, Stay at the Historical Cropp Mansion, Charming riverfront home with fireplace, patio, grill, & full kitchen, Sodo Landing, Moonrise Suite in a Vineyard + Winery!

Top trending hotels in Enterprise

SureStay Plus by Best Western Enterprise

SureStay Plus by Best Western Enterprise

2.5 out of 5
1200 Highland Avenue, Enterprise, OR
Fully refundableReserve now, pay when you stay
Located in Enterprise, SureStay Plus by Best Western Enterprise is in the mountains, within a 5-minute drive of Wallowa River and Enterprise Public Library.
SureStay Plus by Best Western Enterprise
The Ponderosa Motel

The Ponderosa Motel

2.5 out of 5
12 E Greenwood St, Enterprise, OR
Fully refundableReserve now, pay when you stay
With a stay at The Ponderosa Motel in Enterprise, you'll be a 3-minute walk from Enterprise Public Library and 14 minutes by foot from Wallowa River.
The Ponderosa Motel
Lakefront lodge with amazing view, private dock, rec room - dog-friendly

Lakefront lodge with amazing view, private dock, rec room - dog-friendly

Joseph
When you stay at this vacation home in Enterprise, you'll be on the waterfront, just steps from Wallowa Lake and 3 minutes by foot from Wallowa-Whitman National ...
Lakefront lodge with amazing view, private dock, rec room - dog-friendly
Save an average of 15% on thousands of hotels when you're signed in
Experience a one-of-a-kind stay at Mt

Experience a one-of-a-kind stay at Mt

Enterprise
A stay at this condo places you in the heart of Enterprise, steps from Enterprise Public Library and 14 minutes by foot from Wallowa Memorial Hospital.
Experience a one-of-a-kind stay at Mt
Don't see what you're looking for?
See all available properties in Enterprise
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.