Bend Vacation Rentals

Compare 32 vacation rentals. Enter your trip dates to get started.
USA > Oregon > Bend

Make Bend your next getaway—choose from 32 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

housing_type_house.jpg

House rentals

View 14 House rentals
housing_type_condo.jpg

Condo rentals

View 11 Condo rentals
housing_type_duplex.jpg

Duplexes

View 3 Duplexes

Bend vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Broken Top Condo 3D Tour
2 Bed | 2 Bath | Sleeps 7

Broken Top Condo - Bend, OR

From $152
Mt Bachelor Village - Seclusion in Century West 3D Tour
0 Bed | 1 Bath | Sleeps 2

Mt Bachelor Village - Seclusion in Century West - Bend, OR

From $55
Quimby Cottage 3D Tour
1 Bed | 1 Bath | Sleeps 4

Quimby Cottage - Bend, OR

From $83
Seventh Heaven 3D Tour
1 Bed | 2 Bath | Sleeps 4

Seventh Heaven - Bend, OR

From $83
Wall Street Condo #114 3D Tour
1 Bed | 2 Bath | Sleeps 4

Wall Street Condo #114 - Bend, OR

From $61

View 27 more homes

Recent Bend vacation rental reviews

Pros: Spacious and clean Comfortably sleeps 5 Well equipped kitchen Washer and Dryer Cons/Quirks: Flat pillows Prickly bush obstructing driveway Tsunami like shower head in hall bath Possessed remote making it impossible to use TV Dryer rings every couple minutes while in use
Katie C. | Jul 2021
We loved the space! We did have a bit of an issue with the internet service not properly connecting so we were unable to use the TV, but honestly we spent so much time outside and on the balcony we didn't have time to watch any Netflix!
Julie K. | Jul 2021
Wonderful view from the deck and the bed was very comfortable as well. Kitchen well appointed. We would stay here again!
Lisa R. | Jul 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.