Enterprise Vacation Packages 2025/2026

Name: Lakefront lodge with amazing view, private dock, rec room - dog-friendly
Address: Joseph
Rating: 9.4

Plan, book, travel with confidence

Better together

Save up to $1,045 when you book a flight and hotel together*

Find the right fit

With over 300,000 hotels worldwide, it's easy to create a perfect package

Rest easy

Plan, book, and manage your trip all in one place

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.

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.

Enterprise Hotel Deals

SureStay Plus by Best Western Enterprise

1200 Highland Avenue, Enterprise, OR

Fully refundableReserve now, pay when you stay

$133 nightly

$148 total

Oct 1 - Oct 2

Total with taxes and fees

9.2/10 Wonderful! (600 reviews)

"Good"

Reviewed on Sep 8, 2025

The Ponderosa Motel

12 E Greenwood St, Enterprise, OR

Fully refundableReserve now, pay when you stay

$151 nightly

$169 total

Sep 17 - Sep 18

Total with taxes and fees

8.4/10 Very Good! (344 reviews)

Nice place to stay.

"Staff was VERY helpful because we had to traverse 18 steps to our room. Not so good for 80 and 82 year olds and they helped with luggage. Motel only 1 1/2 block from AWESOME local bakery/sandwich place."

Reviewed on Sep 9, 2025

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

See all 317 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.

More vacations you might like

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.

Unlock instant savings with Member Prices

Enterprise Vacations

Book a Hotel + Flight or Car together to unlock savings

Room 1

Plan, book, travel with confidence