Enterprise Vacations

Book a Hotel + Flight or Car together to unlock savings

Your Enterprise Vacation

Reserve a Enterprise vacation package and concentrate on what matters — having fun. No more planning headaches, just more free time to uncover what's special about this lively city, such as its friendly locals and rural countryside. Fill your spare time with tours of Wallowa River, Wallowa County Museum and Alpine Meadows Golf Course, some of the top attractions you just have to see during your trip to Enterprise. Whoever you're escaping with and whatever you want to spend, your ultimate Enterprise vacation is just a few clicks away with Expedia.

Discover the most popular places to visit in Enterprise

Red Hill Lookout

Learn about the local history of Enterprise when you take a trip to Red Hill Lookout. Wander the lakeside or discover the mountain views in this family-friendly area.

Red Hill Lookout

Chief Joseph Canyon Creek Trail

Explore the great outdoors at Chief Joseph Canyon Creek Trail, a lovely green space in Flora. Make some time to visit the monuments while you're in the area.

Chief Joseph Canyon Creek Trail

Enterprise Hotel Deals

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
$122 nightly
The price is $136 total per night from Nov 4 to Nov 5
$136 total
Nov 4 - Nov 5
Total with taxes and fees
9.2/10 Wonderful! (616 reviews)
"The trip was fine. The only drawback was the beds were not comfortable. Other than that everything else was great. Excellent service excellent staff the beds were a drawback."

Reviewed on Oct 19, 2025

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
$114 nightly
The price is $128 total per night from Oct 23 to Oct 24
$128 total
Oct 23 - Oct 24
Total with taxes and fees
8.4/10 Very Good! (353 reviews)
"Nice place! Nice people!"

Reviewed on Oct 7, 2025

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
9.4/10 Exceptional! (27 reviews)
"the property was incredible and our VRBO contact was helpful. We were, sadly, staying after a party before us who left the property in poor shape requiring a later check in that we hoped. In addition the previous guest had smoked indoors leaving a lingering odor and neglected to turn off the gas ..."

Reviewed on Aug 21, 2025

Get rates
Lakefront lodge with amazing view, private dock, rec room - dog-friendly
See all 311 properties in Enterprise
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.

Find the Best Enterprise Vacation Packages

Enterprise Essential Information

Language
English
Currency
U.S dollars
Population
1,950
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Wallowa Lake State Park, Wallowa Lake Tramway and Wallowa County Museum

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Frequently asked questions

How much does an Enterprise vacation package cost?
You'll find cheap prices on Expedia for your Enterprise break. However, factors like the length of stay, hotel choice and season will determine how much your vacation to Enterprise costs.
What are the cheapest months to go to Enterprise?
If you're looking to book a cheap Enterprise vacation package, consider traveling in October, November and December. You'll usually find lower rates on airfares and hotels during these months — ideal for budget-conscious travelers.
How many days is enough for Enterprise?
The ideal length of your Enterprise vacation depends on what you'd like to see. Typically, a few days to a week will give you plenty of time to hit all the main attractions and discover some hidden spots along the way.
How to find the best Enterprise package deals?
Begin your search for an Enterprise package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Enterprise package deal straight away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Enterprise escape underway.
Is it cheaper to book an Enterprise vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component individually. And you'll still have the flexibility to create a tailored Enterprise vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Enterprise?
Enjoy incredible bargains by booking your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for a spur-of-the-moment Enterprise adventure.
Does Expedia offer Book Now, Pay Later Enterprise vacation packages?
Your Enterprise break is meant to be a relaxing escape from your busy life, not a reason for money worries. So to give you that extra flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.