Book Holiday Homes in Enterprise

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Featured Holiday Homes in Enterprise

The Lasater Ranch - country comfort, close to wineries

The Lasater Ranch - country comfort, close to wineries

Walla Walla
Located in Walla Walla, this vacation home is in a rural location, within a 5-minute drive of Northstar Winery and Walla Walla Stateline Loop.
Opens in a new windowThe Lasater Ranch - country comfort, close to wineries
Classic Cabin w/ Gas Fireplace & Large Yard - Walk to the Lake, Dogs Welcome

Classic Cabin w/ Gas Fireplace & Large Yard - Walk to the Lake, Dogs Welcome

Joseph
When you stay at this vacation home in Joseph, you'll be in the mountains, within a 15-minute walk of Wallowa Lake and Wallowa River.
Opens in a new windowClassic Cabin w/ Gas Fireplace & Large Yard - Walk to the Lake, Dogs Welcome
Marybelle’s Vacation Rental

Marybelle’s Vacation Rental

Walla Walla
With a stay at this vacation home in Walla Walla, you'll be within a 5-minute drive of Pioneer Park Aviary and Jumpin' Jellybeanz.
Opens in a new windowMarybelle’s Vacation Rental
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Heritage Heights-Close to Downtown & Pioneer Park - Luxury Finishes - EV charger

Heritage Heights-Close to Downtown & Pioneer Park - Luxury Finishes - EV charger

Walla Walla, WA
A stay at this vacation home places you in the heart of Walla Walla, within a 10-minute walk of Whitman College and Pioneer Park Aviary.
Opens in a new windowHeritage Heights-Close to Downtown & Pioneer Park - Luxury Finishes - EV charger
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
With a stay at this vacation home in Enterprise, you'll be in the mountains, within a 5-minute drive of Wallowa Lake and Wallowa-Whitman National Forest.
Opens in a new windowCustom-built log home w/ gas grill, free WiFi, deck, and private location
The Schoolhouse · The Schoolhouse

The Schoolhouse · The Schoolhouse

Walla Walla
With a stay at this vacation home in Walla Walla, you'll be a 5-minute walk from Whitman College and 5 minutes by foot from Kirkman House Museum.
Opens in a new windowThe Schoolhouse · The Schoolhouse
 The Wild Iris House

The Wild Iris House

Joseph
With a stay at this vacation home, you'll be centrally located in Joseph, within a 10-minute drive of Wallowa Lake and Wallowa County Museum.
Opens in a new window The Wild Iris House
HEATED Pool & Hot Tub in a Quiet Neighborhood- Walk to Town- Dog Friendly

HEATED Pool & Hot Tub in a Quiet Neighborhood- Walk to Town- Dog Friendly

Walla Walla
Located in Walla Walla, this vacation home is within a 5-minute drive of Whitman College and Jumpin' Jellybeanz.
Opens in a new windowHEATED Pool & Hot Tub in a Quiet Neighborhood- Walk to Town- Dog Friendly
Lasater Ranch Bunkhouse- close to town & wineries!

Lasater Ranch Bunkhouse- close to town & wineries!

2 out of 5
Walla Walla
Located in Walla Walla, this vacation home is in a rural location, within a 5-minute drive of Northstar Winery and Walla Walla Stateline Loop.
Opens in a new windowLasater Ranch Bunkhouse- close to town & wineries!
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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
193 Holiday Homes
Lowest Price
AU$195
Highest Price
AU$208
Popular accommodation
The Lasater Ranch - country comfort, close to wineries, Classic Cabin w/ Gas Fireplace & Large Yard - Walk to the Lake, Dogs Welcome, Marybelle’s Vacation Rental, Heritage Heights-Close to Downtown & Pioneer Park - Luxury Finishes - EV charger, Custom-built log home w/ gas grill, free WiFi, deck, and private location, The Schoolhouse · The Schoolhouse, The Wild Iris House, HEATED Pool & Hot Tub in a Quiet Neighborhood- Walk to Town- Dog Friendly, Lasater Ranch Bunkhouse- close to town & wineries!

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 AU$208 per night from 9 Nov to 10 Nov
AU$208
9 Nov - 10 Nov
includes taxes & fees
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.
Opens in a new windowSureStay Plus by Best Western Enterprise
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 ...
Opens in a new windowLakefront lodge with amazing view, private dock, rec room - dog-friendly
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 AU$195 per night from 4 Nov to 5 Nov
AU$195
4 Nov - 5 Nov
includes taxes & fees
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.
Opens in a new windowThe Ponderosa Motel
Save an average of 15% on thousands of hotels when you're signed in
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
With a stay at this vacation home in Enterprise, you'll be in the mountains, within a 5-minute drive of Wallowa Lake and Wallowa-Whitman National Forest.
Opens in a new windowCustom-built log home w/ gas grill, free WiFi, deck, and private location
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.