Bend Vacation Rentals

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USA > Oregon > Bend

Make Bend your next getaway—choose from 37 great vacation rentals

With Mt. Bachelor just twenty minutes away, the Deschutes River winding past, and a slew of award-winning restaurants and breweries to visit, Bend has become one of the most popular vacation destinations in Central Oregon for a very good reason. And whether you seek a cozy vacation cabin for two or a spacious dog-friendly retreat for a family reunion, we have the perfect vacation rental for your next getaway!

Explore Bend house rentals, condo rentals, duplexes, and more

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House rentals

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Condo rentals

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Duplexes

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Bend vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Ponderosa Views 3D Tour
1 Bedroom | 1 Bath | Sleeps 4

Ponderosa Views - Bend, OR

From $57
Deschutes Riverside Escape 3D Tour
0 Bedroom | 1 Bath | Sleeps 2

Deschutes Riverside Escape - Bend, OR

From $49
Amazing Luxury Downtown Old Mill Home 3D Tour
2 Bedroom | 2 Bath | Sleeps 6

Amazing Luxury Downtown Old Mill Home - Bend, OR

From $139
Seventh Mountain Luxury 3D Tour
1 Bedroom | 1 Bath | Sleeps 4

Seventh Mountain Luxury - Bend, OR

From $60
Mt Bachelor Village Ski House # 262 3D Tour
1 Bedroom | 1.5 Bath | Sleeps 6

Mt Bachelor Village Ski House # 262 - Bend, OR

From $95

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Recent Bend vacation rental reviews

The house was perfect for our family. We enjoyed the open kitchen and had plenty of room. We didn't realize the hot tub was out of service would have enjoyed our football games on a larger tv. otherwise it was perfect.
Roby T. | Dec 2021
Clean, family friendly. Equipped with the basic necessities.
David D. | Dec 2021
LOTS of sleeping space for a small unit, easy to access, nice location next to Pioneer Park, and really well laid out! The mini-split HVAC units were not the greatest at keeping the unit warm on cold nights - had to get a space heater from Vacasa (which they provided quickly). Also there were extra blankets, all of which we used! Thank you this was lovely, would stay here again.
Tamara R. | Dec 2021

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Where is Bend, OR?

Tucked between Redmond, OR to the north and the beautiful resort area of Sunriver to the south, our Bend vacation rentals and cabins put you within easy reach of many Central Oregon highlights - including gorgeous Smith Rock in Terrebonne! Bend offers all of the highlights of the Pacific Northwest (outdoor recreation, amazing beer, locally-sourced cuisine), plus 300 days of sunshine for a true year-round destination. 

Outdoor activities in Bend, OR

Of course, many visitors come to explore Mt. Bachelor: skiing, snowboarding, snowshoeing, and cross-country skiing opportunities are everywhere in the winter, with amazing mountain biking and hiking trails in the late summer.

The Deschutes River winds through the city, offering a beautiful riverside trail for biking and jogging in the summer and snowshoeing in the winter. Get to know the river a little better by kayak, or book a guided trip on a whitewater raft or with a fly-fishing pole in hand. For even more adventure, try your hand at rock climbing, or head underground on a caving expedition. There are numerous golf courses to choose from, and miles of trails of varying difficulty to keep all cyclists happy.

Things to do in Bend, OR

All that exercise works up quite an appetite, and Bend is ready for you! Your options range from fine dining to homespun cafes, but you might pass them all by in favor of the wonderful brewpubs that have sprung up over the last decade. The city even offers an atlas and passport as you explore the Bend Ale Trail.

Staying in a Bend vacation cabin rental is a wonderful way to experience this unique Central Oregon city. Sip your morning coffee on your cozy front porch, or stroll downtown to a local cafe for a cappuccino. Stock up on the freshest, most local groceries at the seasonal farmers' market, and enjoy Oregon's bounty in the comfort of your own kitchen. Several of our vacation rentals have cozy fireplaces for chilly winter nights, and a few offer pet-friendly accommodations for a very dog-friendly town.

The downtown area and the Old Mill District, a former industrial zone turned entertainment area, are prime destinations for shopping and dining.

Day trips from Bend, OR

If you feel like exploring a bit, the nearby town of Sisters is only 20 miles north. Home of the Annual Sisters Rodeo in June, this old-fashioned town has a real Western vibe with shops, galleries, and restaurants. Just 26 miles north of Bend, visit Smith Rock State Park in Terrebonne. For what it lacks in size, this small state park doesn't hold back in breathtaking beauty.

Whether your plans take you to the top of Mt. Bachelor or just to the brewery around the corner, you'll thoroughly enjoy coming back to your cozy Bend vacation rental.