Bend, OR, USA

Bend, OR, USA

We found 2,217 vacation rentals — enter your dates for availability


Find the best place to stay — Bend

Where to stay around Bend, OR?

Our 2018 property listings offer a large selection of 2,217 vacation rentals near Bend. From 1,438 houses to 246 condos, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Bend for a holiday or a weekend are on HomeAway.

Bend—gateway to the great outdoors

Bend’s strategic location at a narrow point on the Deschutes River marked it out as an ideal crossing point for the early pioneers, who named the spot “Farewell Bend.” The town grew up during the early years of the 20th century to serve a local sawmill, while its striking focal point of Mirror Pond was created when the river was dammed for power in 1910. Today it’s one of Oregon’s most picturesque and popular vacation hot spots, with Mount Bachelor attracting winter-sports enthusiasts, Cascade Lakes appealing to fishing and hiking fans, and Bend vacation rentals providing a year-round gateway to the great outdoors.

Best of both worlds in Bend

The Mount Bachelor ski resort is one of the largest winter-sports areas in the Pacific Northwest, known for its impressively long season, which typically lasts from mid-November through May. Conditions are ideal for a wide variety of activities, from Nordic skiing to snowboarding and dog sledding, while in summer, the downhill runs are transformed into mountain biking trails of varying levels of difficulty. The resort is around 22 miles west of Bend, which hosts a thriving après-ski scene in its lively bars and restaurants. Basing yourself in downtown Bend vacation rentals allows you to enjoy the best of both worlds.

Showcasing Bend’s heritage

The High Desert Museum combines wildlife and art in a unique combination of indoor and outdoor displays. Its mission is to showcase the region’s natural and cultural heritage through real-life habitats and living history demonstrations. The museum itself is built from slate and volcanic rocks set among aspens and ponderosa pines, with paved pathways linking the outdoor exhibits. Highlights include a reconstruction of a town from the 1860s, a stunning collection of Native American horse tack, paintings and sculptures by the so-called “cowboy artist,” Charles Marion Russell, and a spectacular birds of prey center.

Bend’s seasonal appeal

Bend’s famous Indian summers are the perfect excuse for a late-season getaway before winter sets in. Snow typically falls for several months, extending the ski season well into late spring. Demand for Bend vacation rentals peaks during the height of the winter holiday season from Thanksgiving to New Year, so you’ll need to book well ahead for the best rates and availability at this popular time. The summer months bring dry, sunny days and cool nights, with the fresh mountain air providing a pleasant diversion from the big-city heat.

Bend’s world-famous waterway

The Deschutes River was a vital waterway for pioneers on the Oregon Trail and the Native Americans before them. The river flows through the rugged hillsides of central Oregon and supplies valuable irrigation to this arid habitat. Columbia River redband trout, known locally as “redsides” for their characteristic red stripe, abound in its hospitable waters. Fly-fishers from all over the world converge on riverside Bend vacation rentals during late May and early June, when the conditions are perfect for landing trout, salmon, bass, and sticklebacks.