Book Holiday Homes in Enterprise

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Featured Holiday Homes in Enterprise

Steps from downtown - Beautiful historic home with AC, WiFi

Steps from downtown - Beautiful historic home with AC, WiFi

Walla Walla
With a stay at this vacation home in Walla Walla, you'll be within a 10-minute walk of Whitman College and Jumpin' Jellybeanz.
Opens in a new windowSteps from downtown - Beautiful historic home with AC, WiFi
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
Updated 1939 cottage with beautiful park view

Updated 1939 cottage with beautiful park view

Walla Walla
With a stay at this vacation home in Walla Walla, you'll be within a 15-minute walk of Pioneer Park Aviary and Whitman College.
Opens in a new windowUpdated 1939 cottage with beautiful park view
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Reser Ranch · Reser Ranch, Updated Rancher - Close to Everything

Reser Ranch · Reser Ranch, Updated Rancher - Close to Everything

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 windowReser Ranch · Reser Ranch, Updated Rancher - Close to Everything
Sewah Retreat · Charming Craftsman Cottage - Walkable to Town

Sewah Retreat · Charming Craftsman Cottage - Walkable to Town

Walla Walla
With a stay at this vacation home, you'll be centrally located in Walla Walla, just a 3-minute walk from Whitman College and 9 minutes by foot from Kirkman House ...
Opens in a new windowSewah Retreat · Charming Craftsman Cottage - Walkable to Town
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
The Oasis Downtown 3 BR with Pool

The Oasis Downtown 3 BR with Pool

Walla Walla
The price is AU$807 per night from 22 Sept to 23 Sept
AU$807
22 Sept - 23 Sept
includes taxes & fees
A stay at this vacation home places you in the heart of Walla Walla, steps from Whitman College and 7 minutes by foot from Jumpin' Jellybeanz.
Opens in a new windowThe Oasis Downtown 3 BR with Pool
Heritage Heights-Close to Downtown & Pioneer Park

Heritage Heights-Close to Downtown & Pioneer Park

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
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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$192
Highest Price
AU$807
Popular accommodation
Steps from downtown - Beautiful historic home with AC, WiFi, The Schoolhouse · The Schoolhouse, Updated 1939 cottage with beautiful park view, Reser Ranch · Reser Ranch, Updated Rancher - Close to Everything, Sewah Retreat · Charming Craftsman Cottage - Walkable to Town, Classic Cabin w/ Gas Fireplace & Large Yard - Walk to the Lake, Dogs Welcome, Marybelle’s Vacation Rental, The Oasis Downtown 3 BR with Pool, Heritage Heights-Close to Downtown & Pioneer Park

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$227 per night from 19 Oct to 20 Oct
AU$227
19 Oct - 20 Oct
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
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$192 per night from 19 Oct to 20 Oct
AU$192
19 Oct - 20 Oct
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
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
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
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.