Enterprise Vacation Packages 2026 from $919

Enterprise flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Quality Inn Umatilla - Hermiston

$919

per person

Nov 25 - Nov 29

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Pendleton (PDT)

A golf course and a gym are featured at this hotel. There's fun for all ages with mini golf and an arcade/game room, and barbecue grills are available on site. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.

Top Enterprise hotels deals

The Ponderosa Motel

12 E Greenwood St Enterprise OR

Free Cancellation

Reserve now, pay when you stay

$112 nightly

$125 total

Oct 18 - Oct 19

Total with taxes and fees

Free WiFi in public areas is available at this motel. Take advantage of the free self parking.

Pet friendly

Parking included

SureStay Plus by Best Western Enterprise

1200 Highland Avenue Enterprise OR

Free Cancellation

Reserve now, pay when you stay

$128 nightly

$143 total

Oct 25 - Oct 26

Total with taxes and fees

This hotel features an indoor pool and a gym. Enjoy the hot tub and free perks like continental breakfast and free self parking. Enjoy the sauna and conveniences like a terrace and laundry facilities.

Pool

Hot Tub

Golden Saddle lakefront log home-Wallowa Lake

Joseph OR

Get rates

This vacation home features barbecue grills.

Kitchen

Washer

Twin Peaks is part of the Litch Hotel: fully equipped,Luxury vacation rental condos

Enterprise OR

$261 nightly

$279 total

Oct 26 - Oct 27

Total with taxes and fees

Stay at this condo in Enterprise. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Enterprise Public Library and Alpine Meadows Golf Course are located nearby.

Kitchen

Free WiFi

Sacajawea is part of the Litch Hotel: Luxury fully equipped vacation rental condos

Enterprise OR

$297 nightly

$316 total

Oct 26 - Oct 27

Total with taxes and fees

Stay at this condo in Enterprise. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Enterprise Public Library and Alpine Meadows Golf Course are located nearby.

Kitchen

Free WiFi

Peaceful log cabin retreat with wildlife, mountain and lake views

Joseph OR

Get rates

This vacation home includes a garden and barbecue grills.

Kitchen

Washer

Don't see what you're looking for?

See all available properties in Enterprise

View all properties

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.

Stay near popular Enterprise attractions

Red Hill Lookout

8.6/10 (10 reviews)

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.

See properties

Frequently asked questions

How much are vacation packages to Enterprise?

You'll find an amazing flight and hotel bundle for a mere $919. With one of our Travelocity vacation packages, a stay in Enterprise has never looked so tempting! Save both time and cash and get an early start with packing your suitcases.

How long should my Enterprise vacation be?

There are no firm rules when it comes to how long your vacation in Enterprise should be, but many travelers choose to stay around 2 nights. Got some wiggle room in your departure date? Consider booking a few more nights. Then you'll have enough time to discover some lesser-known areas as well.

Where can I get the best vacation package deals for Enterprise?

With as many as 400 airline partners and 1,000,000 properties around the world, it's hard to go past Travelocity. Take advantage of our extensive range and score an incredible package deal to Enterprise. Doesn't it feel amazing when organizing a trip is that easy?

Why should I purchase my Enterprise vacation package with Travelocity?

With first-rate service, customer support available 24/7 and some of the most gorgeous getaways on offer, you'll never wander alone. And if you find a cheaper price, we'll match it. That's our Price Match Guarantee.

Can I save money on my Enterprise car rental if I combine it with a hotel or flight?

You sure can. And our Enterprise vacation packages will help you do it. In only a few clicks you can save money as well as time by combining your bookings. Collect the keys to your rental car and do your vacation your way. Need to fill your itinerary? Add a few tours to your package and save on those too.

What is there to do in Enterprise?

Alpine Meadows Golf Course is just one of the memorable sights that make Enterprise such a popular tourist destination. But leave some extra time to explore the city's lesser-known attractions too. This is sometimes where the best memories are made.

Where should I stay when visiting Enterprise?

If you're after a place to base yourself, have a look at the SureStay Plus by Best Western Enterprise. It's the top choice for many visitors.