Book Holiday Homes in Enterprise

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Featured Holiday Homes in Enterprise

Walla Walla Gem - Peaceful, Private and a Perfect Central Location

Walla Walla Gem - Peaceful, Private and a Perfect Central Location

Walla Walla
When you stay at this vacation home in Walla Walla, you'll be on the waterfront, within a 10-minute walk of Jumpin' Jellybeanz and Downtown Farmers Market.
Walla Walla Gem - Peaceful, Private and a Perfect Central Location
3BR/3.5BA Modern Downtown Townhome on Mill Creek with Stunning Rooftop Deck

3BR/3.5BA Modern Downtown Townhome on Mill Creek with Stunning Rooftop Deck

Walla Walla
A stay at this vacation home places you in the heart of Walla Walla, within a 5-minute walk of Gesa Power House Theatre and Downtown Farmers Market.
3BR/3.5BA Modern Downtown Townhome on Mill Creek with Stunning Rooftop Deck
Family- and dog-friendly loft with fast WiFi & full kitchen - walkable location

Family- and dog-friendly loft with fast WiFi & full kitchen - walkable location

Joseph
A stay at this vacation home places you in the heart of Joseph, within a 5-minute walk of Maxville Heritage Interpretive Center and Valley Bronze Gallery & ...
Family- and dog-friendly loft with fast WiFi & full kitchen - walkable location
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Wonderful Juniper Guest House in Walla Walla

Wonderful Juniper Guest House in Walla Walla

Walla Walla
The price is AU$693 per night from 29 Dec to 30 Dec
AU$693
includes taxes & fees
29 Dec - 30 Dec
A stay at this vacation home places you in the heart of Walla Walla, within a 15-minute walk of Whitman College and Pioneer Park Aviary.
Wonderful Juniper Guest House in Walla Walla
Lakefront home with amazing lake view, private dock & deck

Lakefront home with amazing lake view, private dock & deck

Joseph
When you a stay at this vacation home in Joseph, you'll be on the waterfront, within a 5-minute walk of Wallowa Lake and Wallowa River.
Lakefront home with amazing lake view, private dock & deck
Pine Tree Cabin - Pet Friendly! Home away from home!

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

Enterprise
The price is AU$387 per night from 24 Dec to 25 Dec
AU$387
includes taxes & fees
24 Dec - 25 Dec
With a stay at this vacation home in Enterprise, you'll be within a 10-minute walk of Enterprise Public Library and Wallowa Memorial Hospital.
Pine Tree Cabin - Pet Friendly! Home away from home!
The Alder house with a Park view!

The Alder house with a Park view!

Walla Walla
A stay at this vacation home places you in the heart of Walla Walla, within a 15-minute walk of Pioneer Park Aviary and Whitman College.
The Alder house with a Park view!
Bryant Barn:  Sleep Inside A Wine Barrel, Fire Pit, Big Yard

Bryant Barn: Sleep Inside A Wine Barrel, Fire Pit, Big Yard

Walla Walla
A stay at this vacation home places you in the heart of Walla Walla, within a 5-minute drive of Pioneer Park Aviary and Whitman College.
Bryant Barn: Sleep Inside A Wine Barrel, Fire Pit, Big Yard
The Willows · The Willows is Enchanting

The Willows · The Willows is Enchanting

Walla Walla
Located in Walla Walla, this vacation home is within a 15-minute walk of Whitman College and Pioneer Park Aviary.
The Willows · The Willows is Enchanting
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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
130 Holiday Homes
Lowest Price
AU$204
Highest Price
AU$693
Popular accommodation
Walla Walla Gem - Peaceful, Private and a Perfect Central Location , 3BR/3.5BA Modern Downtown Townhome on Mill Creek with Stunning Rooftop Deck, Family- and dog-friendly loft with fast WiFi & full kitchen - walkable location, Wonderful Juniper Guest House in Walla Walla, Lakefront home with amazing lake view, private dock & deck, Pine Tree Cabin - Pet Friendly! Home away from home!, The Alder house with a Park view!, Bryant Barn: Sleep Inside A Wine Barrel, Fire Pit, Big Yard, The Willows · The Willows is Enchanting

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$218 per night from 28 Dec to 29 Dec
AU$218
includes taxes & fees
28 Dec - 29 Dec
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
The price is AU$204 per night from 24 Dec to 25 Dec
AU$204
includes taxes & fees
24 Dec - 25 Dec
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
Located in Enterprise, this vacation home is on the waterfront, within a 5-minute walk of Wallowa Lake and Wallowa-Whitman National Forest.
Lakefront lodge with amazing view, private dock, rec room - dog-friendly
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Experience a one-of-a-kind stay at Mt

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

Enterprise
The price is AU$309 per night from 6 Jan to 7 Jan
AU$309
includes taxes & fees
6 Jan - 7 Jan 2025
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
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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.