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Bend Vacation Rentals

1 - 42 of 305 rentals
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 Skyliner Condo #181 - Bend, OR Vacation Rental

Skyliner Condo #181

Bend, OR
1 Bed 2 Bath Sleeps 4
- - - - 85 90 70 70 70 70 70 99 99 70 70 70 70
Deschutes Condo #145 - Bend, OR Vacation Rental

Deschutes Condo #145

Bend, OR
1 Bed 2 Bath Sleeps 4
70 70 70 - - 75 70 70 70 70 70 99 99 70 70 70 70
Summit Condo #178 - Bend, OR Vacation Rental

Summit Condo #178

Bend, OR
1 Bed 2 Bath Sleeps 4
70 - 70 70 75 75 70 70 70 70 70 80 75 - - - -
Westside Loft Rental w/Hot Tub - Bend, OR Vacation Rental
75 80 80 80 99 99 85 85 85 99 99 115 115 99 99 99 99
Wall Street Condo #114 - Bend, OR Vacation Rental

Wall Street Condo #114

Bend, OR
1 Bed 2 Bath Sleeps 4
70 70 70 70 - - - 70 70 70 70 80 80 65 65 65 65
Seventh Mountain Luxury - Bend, OR Vacation Rental

Seventh Mountain Luxury

Bend, OR
1 Bed 1 Bath Sleeps 4
90 99 99 99 115 115 99 99 99 99 99 - - - 99 99 99
Deschutes Landing at the Old Mill Riverfront - Bend, OR Vacation Rental
115 125 125 115 - - 140 145 145 155 155 195 185 - - - -
The Drake Condo  #146 - Bend, OR Vacation Rental

The Drake Condo #146

Bend, OR
1 Bed 2 Bath Sleeps 4
70 70 70 70 75 75 70 70 70 70 70 80 80 55 55 - -
River Wild at Mt. Bachelor Village - Bend, OR Vacation Rental
- 99 99 - - 130 - - - - - - - - 99 115 115
Deschutes Riverfront - Bend, OR Vacation Rental

Deschutes Riverfront

Bend, OR
2 Bed 2 Bath Sleeps 6 (4 Adults Max)
- - - - - - - 115 120 120 120 160 160 120 120 120 115
Parkview Condo #103 - Bend, OR Vacation Rental

Parkview Condo #103

Bend, OR
1 Bed 2 Bath Sleeps 4
- - - - - - - - - - - - - - - 50 -
 Tumalo - Bend Studio #104 - Bend, OR Vacation Rental

Tumalo - Bend Studio #104

Bend, OR
0 Bed 1 Bath Sleeps 2
70 - - - 70 70 70 70 70 70 70 75 75 60 60 60 60
Mt Bachelor Village Ski House  #244 - Bend, OR Vacation Rental
- - - - - 85 85 85 85 80 - - - - - - -
Congress Condo  #150 - Bend, OR Vacation Rental

Congress Condo #150

Bend, OR
1 Bed 2 Bath Sleeps 4
- - - - - - 70 70 70 70 70 - - 55 55 - -
Deschutes Luxury Log Home - Bend, OR Vacation Rental

Deschutes Luxury Log Home

Bend, OR
4 Bed 5 Bath Sleeps 8 (6 Adults Max)
395 395 395 395 395 395 395 395 395 395 395 395 395 395 395 395 395
Mt Bachelor Village Ski House # 262 - Bend, OR Vacation Rental
99 99 99 99 - - 99 - - - - - - - - - -
Charming Old Mill Homestead - Bend, OR Vacation Rental

Charming Old Mill Homestead

Bend, OR
4 Bed 2.5 Bath Sleeps 10
- - - - - - - - - - - - - - - - -
Mt Bachelor Village Ski House # 219 - Bend, OR Vacation Rental
70 70 70 - - - - - - - - - - - - - -
The Bird's Nest with Hot Tub - Bend, OR Vacation Rental

The Bird's Nest with Hot Tub

Bend, OR
2 Bed 2 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
Bend Traditional w/Hot Tub & Biking trails - Bend, OR Vacation Rental
- - - - - - - - - - - - - - - - -
2 Lark - Sunriver, OR Vacation Rental

2 Lark

Sunriver, OR
5 Bed 3.5 Bath Sleeps 12
- 160 170 160 - - 170 190 190 190 180 - - - 180 180 -
17 Meadow House - Sunriver, OR Vacation Rental

17 Meadow House

Sunriver, OR
2 Bed 2 Bath Sleeps 6
- - - - - 90 75 75 75 75 75 90 90 75 75 75 75
Fairway Lane 1 | Discover Sunriver - Sunriver, OR Vacation Rental
- - - - - - - - - - - - - - - - -
Eagle Crest Huckleberry Getaway - Eagle Crest, OR Vacation Rental
- - - - - 150 125 125 125 125 125 170 170 125 125 125 125
Cypress Lane 06 | Discover Sunriver - Sunriver, OR Vacation Rental
- - - - - - - 150 150 150 150 190 190 150 150 150 150
Cozy Jay Cabin - Sunriver, OR Vacation Rental

Cozy Jay Cabin

Sunriver, OR
2 Bed 2 Bath Sleeps 6 (4 Adults Max)
75 75 75 75 99 99 80 80 80 80 80 99 99 80 80 80 80
Trapper Lane 10 | Discover Sunriver - Sunriver, OR Vacation Rental
- - - - - - - - - - - - - 175 175 175 175
68 Quelah - Sunriver, OR Vacation Rental

68 Quelah

Sunriver, OR
2 Bed 2 Bath Sleeps 6
80 85 85 85 99 99 90 90 90 90 90 115 115 90 90 90 90
Eagle Crest on Ridge Course - Eagle Crest, OR Vacation Rental

Eagle Crest on Ridge Course

Eagle Crest, OR
4 Bed 3.5 Bath Sleeps 16
135 135 135 135 150 150 135 135 135 135 135 - - - 135 135 135
Malheur Lane 12 | Discover Sunriver - Sunriver, OR Vacation Rental
- 99 99 99 - - 115 120 120 120 120 160 160 120 120 120 120
5 Tan Oak - Sunriver, OR Vacation Rental

5 Tan Oak

Sunriver, OR
3 Bed 3 Bath Sleeps 8
- - - - - - 100 100 100 100 100 - - 100 115 115 115
Kinglet Road 37 | Discover Sunriver - Sunriver, OR Vacation Rental
125 125 125 125 170 170 130 130 130 130 130 180 180 130 130 130 130
Shagbark Lane 21 | Discover Sunriver - Sunriver, OR Vacation Rental
- - 125 125 140 140 125 125 125 125 125 145 145 125 125 125 125
Smith Rock Casa - Terrebonne, OR Vacation Rental

Smith Rock Casa

Terrebonne, OR
3 Bed 2 Bath Sleeps 8
120 130 130 130 165 165 135 135 135 135 135 175 175 135 135 135 135
10 Hoodoo - Sunriver, OR Vacation Rental

10 Hoodoo

Sunriver, OR
3 Bed 2 Bath Sleeps 8
- - - - - - - - 115 99 99 165 165 99 99 99 99
15 Lassen Lane - Sunriver, OR Vacation Rental

15 Lassen Lane

Sunriver, OR
4 Bed 3 Bath Sleeps 10
125 125 125 - - 160 125 125 125 125 - - - 125 125 125 125
Salishan Lane 02 | Discover Sunriver - Sunriver, OR Vacation Rental
- - - - - - 295 345 345 295 - - - 345 365 365 365
Eagle Crest Village Loop with Hot Tub - Eagle Crest, OR Vacation Rental
80 80 80 80 99 99 80 80 80 80 80 99 99 80 80 80 80
Sisters Downtown 1930s Cottage with Extra Studio - Sisters, OR Vacation Rental
- - - - - - - - - - - - - - - - -
1 Pine Mountain - Sunriver, OR Vacation Rental

1 Pine Mountain

Sunriver, OR
2 Bed 3 Bath Sleeps 8
90 99 99 99 130 130 99 99 99 99 99 135 135 99 99 99 99
Hare Lane 05 | Discover Sunriver - Sunriver, OR Vacation Rental
- - - - - - 75 75 75 75 75 99 99 75 75 75 75
Red Cedar 26 | Discover Sunriver - Sunriver, OR Vacation Rental
- 130 130 130 195 195 140 140 140 140 140 220 220 140 140 140 140
Page 1 of 8

About Bend

Bend rated 4.8 out of 5 based on 951 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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