Book Holiday Homes in Enterprise

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Featured Holiday Homes in Enterprise

Comfortable 3BR Home - Cozy

Comfortable 3BR Home - Cozy

2 out of 5
Enterprise OR
The price is NZ$526 per night from 22 Dec to 23 Dec
NZ$526
22 Dec - 23 Dec
includes taxes & fees
Stay at this holiday home in Enterprise. Enjoy laundry facilities, an in-room coffee maker and in-room fireplaces. Popular attractions Enterprise Public Library ...
Opens in a new windowComfortable 3BR Home - Cozy
Serene Japanese Home with Breathtaking Views in Oregon — Only 15 Min to Joseph

Serene Japanese Home with Breathtaking Views in Oregon — Only 15 Min to Joseph

Enterprise OR
Stay at this holiday home in Enterprise. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Alpine Meadows Golf Course and Enterprise Public ...
Opens in a new windowSerene Japanese Home with Breathtaking Views in Oregon — Only 15 Min to Joseph
Custom-built log home w/ gas grill, free WiFi, deck, and private location

Custom-built log home w/ gas grill, free WiFi, deck, and private location

Joseph OR
Stay at this holiday home in Enterprise. Enjoy laundry facilities, patios and an in-room coffee maker. Popular attractions Eagle Cap Wilderness Pack Station ...
Opens in a new windowCustom-built log home w/ gas grill, free WiFi, deck, and private location
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The Woodshed - charming 3 bdrm/1 bath bungalow in Enterprise

The Woodshed - charming 3 bdrm/1 bath bungalow in Enterprise

Enterprise OR
Stay at this holiday home in Enterprise. Enjoy free Wi-Fi, a garden and an in-room coffee maker. Popular attractions Enterprise Public Library and Wallowa River ...
Opens in a new windowThe Woodshed - charming 3 bdrm/1 bath bungalow in Enterprise
Lakefront lodge with private dock, great water view, deck & laundry

Lakefront lodge with private dock, great water view, deck & laundry

Joseph OR
Stay at this holiday home in Enterprise. Enjoy laundry facilities, patios and in-room washers/dryers. Popular attractions Wallowa Lake State Park and Wallowa ...
Opens in a new windowLakefront lodge with private dock, great water view, deck & laundry
Idyllic mountain view cabin with wood fireplace, front deck, bikes, & gas grill

Idyllic mountain view cabin with wood fireplace, front deck, bikes, & gas grill

Joseph OR
Stay at this holiday home in Enterprise. Enjoy a garden, laundry facilities and patios. Popular attractions Eagle Cap Wilderness Pack Station and Wallowa Lake ...
Opens in a new windowIdyllic mountain view cabin with wood fireplace, front deck, bikes, & gas grill
Pine Tree Cabin - Pet Friendly! Home away from home!

Pine Tree Cabin - Pet Friendly! Home away from home!

Enterprise OR
Stay at this holiday home in Enterprise. Enjoy laundry facilities, cable/satellite TV service and an in-room coffee maker. Popular attractions Enterprise Public ...
Opens in a new windowPine Tree Cabin - Pet Friendly! Home away from home!
Cedar Haven Cottage - Pet Friendly! Private BBQ, Deck & Yard

Cedar Haven Cottage - Pet Friendly! Private BBQ, Deck & Yard

Enterprise OR
Stay at this holiday home in Enterprise. Enjoy a garden, laundry facilities and cable/satellite TV service. Popular attractions Enterprise Public Library and ...
Opens in a new windowCedar Haven Cottage - Pet Friendly! Private BBQ, Deck & Yard
Farmhouse Creekside, Next Door to Parks, and Walking distance to Brewery

Farmhouse Creekside, Next Door to Parks, and Walking distance to Brewery

Enterprise OR
Stay at this ski holiday home in Enterprise. Enjoy a garden, laundry facilities and ski-in/ski-out access. Popular attractions Enterprise Public Library and ...
Opens in a new windowFarmhouse Creekside, Next Door to Parks, and Walking distance to Brewery
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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.

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
184 Holiday Homes
Lowest Price
NZ$178
Highest Price
NZ$526
Popular accommodation
Comfortable 3BR Home - Cozy, Serene Japanese Home with Breathtaking Views in Oregon — Only 15 Min to Joseph, Custom-built log home w/ gas grill, free WiFi, deck, and private location, The Woodshed - charming 3 bdrm/1 bath bungalow in Enterprise, Lakefront lodge with private dock, great water view, deck & laundry, Idyllic mountain view cabin with wood fireplace, front deck, bikes, & gas grill, Pine Tree Cabin - Pet Friendly! Home away from home!, Cedar Haven Cottage - Pet Friendly! Private BBQ, Deck & Yard, Farmhouse Creekside, Next Door to Parks, and Walking distance to Brewery

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
The price is NZ$236 per night from 25 Dec to 26 Dec
NZ$236
25 Dec - 26 Dec
includes taxes & fees
Stay at this hotel in Enterprise. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular attractions ...
Opens in a new windowSureStay 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
The price is NZ$221 per night from 20 Dec to 21 Dec
NZ$221
20 Dec - 21 Dec
includes taxes & fees
Stay at this motel in Enterprise. Enjoy free Wi-Fi, free parking and daily housekeeping. Our guests praise the helpful staff and the clean rooms in their reviews. ...
Opens in a new windowThe Ponderosa Motel
The FINCH

The FINCH

2.5 out of 5
325 East Main Street Walla Walla WA
Fully refundableReserve now, pay when you stay
The price is NZ$178 per night from 11 Jan to 12 Jan
NZ$178
11 Jan - 12 Jan 2026
includes taxes & fees
Stay at this golf hotel in Walla Walla. Enjoy free Wi-Fi, free parking and free bicycles on-site. Our guests praise the helpful staff and the clean rooms in ...
Opens in a new windowThe FINCH
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The Marcus Whitman Hotel

The Marcus Whitman Hotel

3.5 out of 5
6 West Rose Street Walla Walla WA
Fully refundableReserve now, pay when you stay
The price is NZ$277 per night from 21 Dec to 22 Dec
NZ$277
21 Dec - 22 Dec
includes taxes & fees
Stay at this historic hotel in Walla Walla. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowThe Marcus Whitman Hotel
Don't see what you're looking for?
See all available properties in Enterprise
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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.