Bend Vacation Rentals

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USA > Oregon > Bend

Make Bend your next getaway—choose from 33 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


House rentals

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Condo rentals

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Bend vacation rentals for every getaway

Dog-friendly Hot tub Internet
Seventh Heaven 3D Tour
1 Bedroom | 2 Bath | Sleeps 4

Seventh Heaven - Bend, OR

From $75
River Wild at Mt. Bachelor Village 3D Tour
3 Bedroom | 2.5 Bath | Sleeps 8

River Wild at Mt. Bachelor Village - Bend, OR

From $142
Deschutes Riverside Escape 3D Tour
0 Bedroom | 1 Bath | Sleeps 2

Deschutes Riverside Escape - Bend, OR

From $49
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
Mt. Bachelor Meridian 3D Tour
1 Bedroom | 1 Bath | Sleeps 4

Mt. Bachelor Meridian - Bend, OR

From $62

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Recent Bend vacation rental reviews

This cozy bungalow offered the perfect retreat for our weekend ladies getaway (4 ladies + 2 dogs)! Walking distance to the Les Schwab Amphitheater and Deschutes River Trail (.6 miles). We encountered a deer in the driveway during our stay and enjoyed the blue jays while drinking Sisters Coffee on the front porch. Highlights of our stay included the High Desert Museum and Northwest Crossing Saturday Market! Will definitely be back, already planning our winter retreat!
Nathaniel W. | Sep 2021
This home was perfect for our trip to Bend Oregon. Everyone slept very comfortably and plenty of places to sit and hangout or read! It's at the top of the hill so the views are amazing, but would definitely want to wear workout clothes/shoes if you were to go on a walk, as the walk back is fairly steep. Not pictured is an awesome grass area in the backyard! Would definitely stay here again!
Kiah H. | Sep 2021
Easily accessible to where you want to go.
Joseph C. | Sep 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.