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Bend Vacation Rentals

1 - 42 of 302 rentals
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Bend Mountain View Retreat - Bend, OR Vacation Rental

Bend Mountain View Retreat

Bend, OR
4 Bed 3.5 Bath Sleeps 10
- - - - 320 340 340 340 445 445 340 340 340 340 340 445 445
River Wild at Mt. Bachelor Village - Bend, OR Vacation Rental
- - - 115 120 120 120 115 - - 115 120 120 115 - - -
Mt Bachelor Village Ski House  #244 - Bend, OR Vacation Rental
- - - - 99 99 99 99 120 120 99 99 99 99 99 120 120
Deschutes Landing at the Old Mill Riverfront - Bend, OR Vacation Rental
- - - - - - - - 195 - - - - - - - 215
Seventh Mountain Luxury - Bend, OR Vacation Rental

Seventh Mountain Luxury

Bend, OR
1 Bed 1 Bath Sleeps 4
99 130 130 115 90 90 90 90 115 115 90 90 90 90 90 115 115
Shanti River House - Near La Pine State Park - Bend, OR Vacation Rental
235 235 235 235 235 235 235 235 235 235 235 235 235 235 235 235 235
Charming Old Mill Homestead - Bend, OR Vacation Rental

Charming Old Mill Homestead

Bend, OR
4 Bed 2.5 Bath Sleeps 10
- - - - - - - - - - - - - - - - -
Deschutes Luxury Log Home - Bend, OR Vacation Rental

Deschutes Luxury Log Home

Bend, OR
4 Bed 5 Bath Sleeps 8 (6 Adults Max)
250 250 250 250 250 250 250 250 250 250 250 250 250 250 250 250 250
Mt Bachelor Village Ski House # 262 - Bend, OR Vacation Rental
99 99 - - 99 99 99 99 115 115 99 99 99 99 99 115 115
Parkview Condo #103 - Bend, OR Vacation Rental

Parkview Condo #103

Bend, OR
1 Bed 2 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
Deschutes Riverfront - Bend, OR Vacation Rental

Deschutes Riverfront

Bend, OR
2 Bed 2 Bath Sleeps 6 (4 Adults Max)
- - - - - - - - - - - - - - - - -
Mt Bachelor Village Ski House # 219 - Bend, OR Vacation Rental
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Deschutes Condo #145 - Bend, OR Vacation Rental

Deschutes Condo #145

Bend, OR
1 Bed 2 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
 Tumalo - Bend Studio #104 - Bend, OR Vacation Rental

Tumalo - Bend Studio #104

Bend, OR
0 Bed 1 Bath Sleeps 2
- - - - - - - - - - - - - - - - -
Westside Loft Rental w/Hot Tub - Bend, OR Vacation Rental
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Congress Condo  #150 - Bend, OR Vacation Rental

Congress Condo #150

Bend, OR
1 Bed 2 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
Summit Condo #178 - Bend, OR Vacation Rental

Summit Condo #178

Bend, OR
1 Bed 2 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
Bend Traditional w/Hot Tub & Biking trails - Bend, OR Vacation Rental
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 Skyliner Condo #181 - Bend, OR Vacation Rental

Skyliner Condo #181

Bend, OR
1 Bed 2 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
The Drake Condo  #146 - Bend, OR Vacation Rental

The Drake Condo #146

Bend, OR
1 Bed 2 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
Wall Street Condo #114 - Bend, OR Vacation Rental

Wall Street Condo #114

Bend, OR
1 Bed 2 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
Salishan Lane 02 | Discover Sunriver - Sunriver, OR Vacation Rental
- - - 195 240 - - - 345 365 270 - - - - - -
6 Umpqua - Sunriver, OR Vacation Rental

6 Umpqua

Sunriver, OR
4 Bed 3 Bath Sleeps 10
130 155 155 135 135 135 135 135 160 160 135 135 135 135 135 160 160
Sisters Gated Estate - Sisters, OR Vacation Rental

Sisters Gated Estate

Sisters, OR
5 Bed 3 Bath Sleeps 20
- - - - 350 350 350 350 - - 350 350 350 350 350 - -
Black Butte Ranch: Spring Home 6 - Black Butte Ranch, OR Vacation Rental
- - - 135 135 135 135 135 - - 135 135 135 135 135 - -
Eagle Crest's Forest Ridge with Hot Tub - Eagle Crest, OR Vacation Rental
115 155 155 125 125 125 125 125 160 160 125 125 120 - - - 140
Hickory Lane 16 | Discover Sunriver - Sunriver, OR Vacation Rental
99 120 120 99 99 99 99 99 125 125 99 99 99 99 99 125 125
5 Tan Oak - Sunriver, OR Vacation Rental

5 Tan Oak

Sunriver, OR
3 Bed 3 Bath Sleeps 8
- - 100 100 100 100 - - - - 100 100 100 100 - - -
27 Tokatee - Sunriver, OR Vacation Rental

27 Tokatee

Sunriver, OR
4 Bed 2 Bath Sleeps 8
125 150 150 125 125 125 125 - - - 125 125 125 125 125 160 160
1 Landrise - Sunriver, OR Vacation Rental

1 Landrise

Sunriver, OR
3 Bed 2 Bath Sleeps 6
99 115 115 99 99 99 99 99 - - - - - - - - -
4 Jay Lane - Sunriver, OR Vacation Rental

4 Jay Lane

Sunriver, OR
3 Bed 3 Bath Sleeps 6
- - - 100 100 100 100 100 100 100 100 100 100 100 100 100 100
6 Flat Top - Sunriver, OR Vacation Rental

6 Flat Top

Sunriver, OR
3 Bed 2 Bath Sleeps 8
- - - 75 80 80 80 80 115 115 80 80 80 80 80 - -
Smith Rock Casa - Terrebonne, OR Vacation Rental

Smith Rock Casa

Terrebonne, OR
3 Bed 2 Bath Sleeps 8
99 - - 99 120 120 120 115 - - 115 120 120 120 115 - -
Shagbark Lane 21 | Discover Sunriver - Sunriver, OR Vacation Rental
115 140 140 115 115 115 115 115 - - - 115 115 115 115 140 140
17 Meadow House - Sunriver, OR Vacation Rental

17 Meadow House

Sunriver, OR
2 Bed 2 Bath Sleeps 6
85 99 99 90 80 80 80 80 99 99 80 80 80 80 80 99 99
Cozy Jay Cabin - Sunriver, OR Vacation Rental

Cozy Jay Cabin

Sunriver, OR
2 Bed 2 Bath Sleeps 6 (4 Adults Max)
75 90 90 80 85 85 85 85 99 99 85 85 85 85 85 85 -
Lynx Lane 08 | Discover Sunriver - Sunriver, OR Vacation Rental
99 - - 99 99 99 99 99 - - 99 99 99 99 99 125 125
6 East Butte Lane - Sunriver, OR Vacation Rental

6 East Butte Lane

Sunriver, OR
2 Bed 2 Bath Sleeps 6
85 - - 85 85 85 - - - 99 - - - 85 - - -
68 Quelah - Sunriver, OR Vacation Rental

68 Quelah

Sunriver, OR
2 Bed 2 Bath Sleeps 6
75 - - 75 80 80 80 80 90 90 75 - - 75 80 90 90
Big Leaf Lane 28 | Discover Sunriver - Sunriver, OR Vacation Rental
- - - - - - - - - - - - - - - - -
Eagle Crest Golfer's Paradise - Eagle Crest, OR Vacation Rental
125 - - 125 165 165 165 165 195 195 165 165 165 160 - - -
Oxnard High Desert Retreat - Sunriver, OR Vacation Rental
99 115 - - - - - - - 115 99 99 99 99 - - -
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About Bend

Bend rated 4.8 out of 5 based on 1006 reviews Bend, OR

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 cabin for two or a spacious retreat for a family reunion, we have the perfect vacation rental for your next getaway!

Where is Bend, OR?

Tucked between Redmond, OR to the north and the beautiful resort area of Sunriver to the south, Bend puts 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

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

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 home is a wonderful way to experience this unique 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

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.

Photo Credit: Gordon-Shukwit via Flickr

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