Bend Vacation Rentals

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USA > Oregon > Bend

Make Bend your next getaway—choose from 30 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
Deschutes Riverside Escape 3D Tour
0 Bed | 1 Bath | Sleeps 2

Deschutes Riverside Escape - Bend, OR

From $58
Taft House 3D Tour
3 Bed | 1 Bath | Sleeps 6

Taft House - Bend, OR

From $116
Linton Loop 3D Tour
4 Bed | 2.5 Bath | Sleeps 8

Linton Loop - Bend, OR

From $127
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 $57
Heyburn House 3D Tour
3 Bed | 2 Bath | Sleeps 6

Heyburn House - Bend, OR

From $89

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Recent Bend vacation rental reviews

This place was perfect for us as it was walkable to Downtown and get our drink on at the breweries. The river is right outside and it was awesome to have some coffee and hangout and chill. When inside of the room, you can not hear the roaring of the river nor anyone walking by, as I believe the windows are double paned. The bed is super big, comfy and clean. The little kitchenette had dishes for us to warm up any leftover food that we had. And it was lovely to have AC in the room as the weekend we were there, was in the high 70s/low 80s outside. We would definitely stay here again any time we are back in Bend.
Ana B. | Jun 2021
Great location, cool house
pete j. | Jun 2021
This condo served us well for 3 weeks. Third floor (only have to walk up 1 1/2 floors of outside stairs from parking). Bedroom and bath were fine - good water pressure in shower. Living room worked well and outside deck had chairs overlooking the forest. Only issues we had we carpet should be replaced, it's seen better days. Be aware, there is no dining table, only 4 bar stools at the counter. There is a combo microwave/oven. Worked well. Could use a better plate/pan for the oven. Stove is 2 burner. Also, there is no cabinet to put food, like your box/cans. We had to leave out on the counter. Facility had many things to do (mini golf, disc golf, tennis/pickle ball, large open grass area. About 15 minute drive to downtown Bend. Good place to access Deschutes River Trail towards town and towards Dillon Falls. Across Century Drive is paved trail for walking.
Curtis L. | Jun 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.