Enterprise Vacations from $249
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.
The Latest Enterprise vacation packages
Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Pendleton
$249
per person
Oct 12 - Oct 15
found 1 day ago
Roundtrip flight included
Portland (PDX) to Pendleton (PDT)
6.2/10 (1,004 reviews)
This was a quick overnight stop on on long road trip. The room was okay - the whole place is a more than a bit run down and could use some TLC. The bed was comfortable, we had all the towels we needed and there was the usual breakfast. Nothing spectacular, but serviceable for a one night stay.
Reviewed on Aug 23, 2026
Motolodge
$292
per person
Oct 12 - Oct 15
found 1 day ago
Roundtrip flight included
Portland (PDX) to Pendleton (PDT)
9/10 Wonderful! (797 reviews)
The location was industrial and a lil suspect. They’re trying their best it seems to make it a nice place to stop off in your travels. Rooms were clean but the furniture needed some replacing with higher quality to withstand cleaning and water sitting stains. Beds were comfortable and pillows too. Cute touches. Downside was the garbage service showed up at 4am and woke the whole block up. Could do some window replacement, landscaping and the hot tub wasn’t functioning when we were there. Staff was super friendly and helpful.
Reviewed on Aug 22, 2026
Stay near popular Enterprise attractions
Red Hill Lookout
8.6/10 (10 reviews)
Perched high in the Wallowa-Whitman National Forest, Red Hill Lookout offers sweeping panoramas of forested mountains and valleys. Accessible via gravel roads from June through September.
Chief Joseph Canyon Creek Trail
9.4/10 (22 reviews)
This alpine trail rewards hikers with sweeping vistas of Wallowa Lake and Eagle Cap Wilderness. Traverse through wildflower-dotted meadows in mid-June for the most spectacular natural displays.
Enterprise Public Library
This 1914 Carnegie-funded library showcases American Renaissance architecture with decorative brickwork and stone elements. Enjoy the serene, well-lit reading rooms that have maintained their original charm.
Alpine Meadows Golf Course
7.8/10 (9 reviews)
Nestled against the stunning Wallowa Mountains, this historic 9-hole course features Trout Creek winding through its fairways. Enjoy challenging undulating greens while soaking in panoramic mountain views.
Enterprise Hotel Deals
The Ponderosa Motel
12 E Greenwood St Enterprise OR
Fully refundableReserve now, pay when you stay
$158 nightly
$177 total
Aug 24 - Aug 25
Total with taxes and fees
SureStay Plus by Best Western Enterprise
1200 Highland Avenue Enterprise OR
Fully refundableReserve now, pay when you stay
$159 nightly
$178 total
Sep 1 - Sep 2
Total with taxes and fees
9.2/10 Wonderful! (673 reviews)
"The continental breakfast was the same every day, I wish there was a variety."
Reviewed on Aug 11, 2026
Peaceful log cabin retreat with wildlife, mountain and lake views
Joseph Oregon
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 |
More vacations you might like
Frequently asked questions
How much does an Enterprise vacation package cost?
You'll find cheap prices from $249 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
- Wallowa County Hotels
- Hotels near Wallowa Memorial Hospital
- Hotels near Alpine Meadows Golf Course
- Hotels near Wallowa River
- Joseph Hotels
- Pet-Friendly Hotels in Joseph
- Best Western Hotels in Joseph
- Condo Rentals in Joseph
- Cabin Rentals in Joseph
- Hotels with Hot Tubs in Joseph
- Family Hotels in Joseph
- Romantic Hotels in Joseph
- 5 Star Hotels in Joseph
- Resorts & Hotels with Spas in Joseph
- Hotels with a Pool in Joseph
- Motels in Joseph
- Hotel Wedding Venues Hotels in Joseph
- Guest Houses in Joseph
- Apartments in Joseph
- Hotels & Resorts for Couples in Joseph
- Cottages in Joseph
- Ski Hotels in Joseph
- Hotels near Valley Bronze Gallery & Foundry
- Hotels near Wallowa County Museum
- Lostine Hotels
- Hotels near Wallowa Lake
- Hotels near Wallowa Lake State Park
- Hotels near Wallowa Lake Tramway
- Hotels near Eagle Cap Wilderness Pack Station
- Hotels near Ferguson Ridge Ski Area
- Wallowa Hotels
- Vacation Homes in Wallowa
- Best Western Hotels in Wallowa
- Luxury Hotels in Wallowa
- 5 Star Hotels in Wallowa
- Motels in Wallowa
- B&B in Wallowa
- Hotels with Air Conditioning in Wallowa
- Imnaha Hotels
- Hotels near Red Hill Lookout
- Cove Hotels
- Hotels near Wallowa County
- Hotels near Imnaha River Valley
- Hotels near Hat Point
- Hotels near Chief Joseph Canyon Creek Trail
- 3 Star Hotels in Flora
- Hotel with a Concierge Hotels in Flora
- Union Hotels
- Cabin Rentals in Union
- Motels in Union
- Elgin Hotels
- Imbler Hotels
- 5 Star Hotels in Imbler
- Hotels near Wallowa-Whitman National Forest
- Hotels near Hot Lake Springs
- Summerville Hotels
- Wallowa River
- Joseph Vacations
- Valley Bronze Gallery & Foundry
- Wallowa County Museum
- Visit Joseph
- Wallowa Lake State Park
- Wallowa Lake Tramway
- Eagle Cap Wilderness Pack Station
- Ferguson Ridge Ski Area
- Wallowa Vacations
- Visit Wallowa
- Visit Imnaha
- Red Hill Lookout
- Imnaha River Valley
- Hells Canyon Dam
- Chief Joseph Canyon Creek Trail
- Flora Vacations
- Oregon Trail Interpretive Center
- Visit Imbler
- Wallowa-Whitman National Forest
- Hot Lake Springs
- Car rentals near Joseph
- Avis Rental Cars in Joseph
- Enterprise Rental Cars in Joseph
- Hertz Rental Cars in Joseph
- Van Car Rentals in Joseph
- Car rentals near Wallowa Lake State Park
- Car rentals near Wallowa
- Dollar Rent A Car Rental Cars in Wallowa
- Car rentals near Imnaha
- Car rentals near Cove
- Car rentals near Flora
- Car rentals near Union
- Car rentals near Elgin
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.