Bend, OR Vacation Packages
Bend is a small but surprisingly bustling city on the Deschutes River in Oregon. To the West are the lakes and peaks of the Cascade Mountains, with ski resorts and multi-use trails. In town, a trail leads up the extinct volcano at Pilot Butte. To the South is the High Desert Museum which showcases the local environment, history, and wildlife exhibits. Stairs at the Newberry National Volcanic Monument lead into the Lava River Cave. With miles of hiking and biking trails through town and access to the Three Sisters mountains, Mt. Bachelor, and Smith Rock nearby, Bend is famous for world-class recreation. Whatever the season, this region offers a vibrant scene, combining small-town friendliness with sophisticated luxury.
Best Bend, OR Vacation Packages:
Oregon Coasts, Cascades, and Gorges Self Drive (Portland - Hood River - Bend - Eugene)
7 nights from $1,177*
A perfect combination of charming cities across Oregon with this unique opportunity to explore on your own with a rental. Combine Portland (Oregon’s largest city, sits on the Columbia and Willamette rivers), Hood River, Bend and Eugene (known as 'Tracktown,' famous for its track and field champions also the birthplace of Nike).
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.
Other Bend, OR Vacation Packages:
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Enjoy a perfect combination of charming cities across Oregon with this unique opportunity to explore on your own with a Rental Car. Combine Portland (Oregon’s largest city, sitting on the Columbia and Willamette rivers), Three Sisters (named for the nearby trio of volcanic mountains where there is an abundance of outdoor activity) and Eugene (known as -Tracktown-, famous for its track and field champions also the birthplace of Nike).
Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city while enjoying included, curated activities that enhance your experience!
Driving Time
Portland - Three Sisters Country: 2 hrs. 50 mins. approx.
Three Sisters Country- Eugene: 2 hrs. approx.
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Bend
Hotels and Activities
SUGGESTED Bend, OR VACATION PACKAGES:
USA Customer Reviews
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Overall, my experience, the trip masters was good, but but I had a problem you couldn’t help. The reason I say this is that we had a problem with a ho ...Traveled on:9/24/2026
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The hotel in Washington DC was very small and the bathroom offered little space and privacy. However, the hotel was eccentric and had fun decorations. ...Traveled on:8/24/2026
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You guys are great! Keep being awesome ...Traveled on:6/12/2026
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It was an excellent trip ...Traveled on:6/5/2026
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I liked the car rental, hotels, flights, and locations. It was quite an adventure! It would have been nice to know of the one-way car rental fee more ...Traveled on:3/29/2026
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