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Bend Vacation Rentals

1 - 42 of 298 rentals
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River Wild at Mt. Bachelor Village - Bend, OR Vacation Rental
135 130 - - - - - - 145 - - - - - 115 115 -
Deschutes Landing at the Old Mill Riverfront - Bend, OR Vacation Rental
145 140 - - - - - - - 245 - - - - - - -
Seventh Mountain Luxury - Bend, OR Vacation Rental

Seventh Mountain Luxury

Bend, OR
1 Bed 1 Bath Sleeps 4
75 70 - - - - - - - 115 - - - - - 115 145
Mt Bachelor Village Ski House  #244 - Bend, OR Vacation Rental
85 85 120 120 99 - - - 99 125 125 99 99 99 99 99 120
Shanti River House - Near La Pine State Park - Bend, OR Vacation Rental
235 - - - 235 - - 235 235 - - 235 235 235 235 235 235
Deschutes Luxury Log Home - Bend, OR Vacation Rental

Deschutes Luxury Log Home

Bend, OR
4 Bed 5 Bath Sleeps 8 (6 Adults Max)
250 250 295 295 270 270 270 270 270 330 330 250 250 250 250 250 250
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 # 262 - Bend, OR Vacation Rental
99 - - - - - - - - - - - - - - 99 99
Parkview Condo #103 - Bend, OR Vacation Rental

Parkview Condo #103

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

Deschutes Condo #145

Bend, OR
1 Bed 2 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
Mt Bachelor Village Ski House # 219 - 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
- - - - - - - - - - - - - - - - -
Deschutes Riverfront - Bend, OR Vacation Rental

Deschutes Riverfront

Bend, OR
2 Bed 2 Bath Sleeps 6 (4 Adults Max)
- - - - - - - - - - - - - - - - -
Westside Loft Rental w/Hot Tub - Bend, OR Vacation Rental
- - - - - - - - - - - - - - - - -
 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
- - - - - - - - - - - - - - - - -
 Tumalo - Bend Studio #104 - Bend, OR Vacation Rental

Tumalo - Bend Studio #104

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

Wall Street Condo #114

Bend, OR
1 Bed 2 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
Bend Traditional w/Hot Tub & Biking trails - Bend, OR Vacation Rental
- - - - - - - - - - - - - - - - -
Summit Condo #178 - Bend, OR Vacation Rental

Summit Condo #178

Bend, OR
1 Bed 2 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
Cozy Jay Cabin - Sunriver, OR Vacation Rental

Cozy Jay Cabin

Sunriver, OR
2 Bed 2 Bath Sleeps 6 (4 Adults Max)
80 80 115 99 - - - - - - - 75 75 - - - -
12 Whistler - Sunriver, OR Vacation Rental

12 Whistler

Sunriver, OR
3 Bed 2.5 Bath Sleeps 8
115 115 170 160 - - - 130 135 180 180 99 99 99 99 - -
4 Jay Lane - Sunriver, OR Vacation Rental

4 Jay Lane

Sunriver, OR
3 Bed 3 Bath Sleeps 6
125 125 165 155 - - - - - 165 175 100 100 100 100 100 115
16 Lassen Lane - Sunriver, OR Vacation Rental

16 Lassen Lane

Sunriver, OR
4 Bed 2 Bath Sleeps 10
135 135 140 - - - - - - - - - - - - - -
15 Lassen Lane - Sunriver, OR Vacation Rental

15 Lassen Lane

Sunriver, OR
4 Bed 3 Bath Sleeps 10
155 155 180 - - - - - - - - - - - - - -
Circle 4 Ranch 31 | Discover Sunriver - Sunriver, OR Vacation Rental
115 115 120 - - - - - - 140 150 90 90 90 90 90 115
17 Meadow House - Sunriver, OR Vacation Rental

17 Meadow House

Sunriver, OR
2 Bed 2 Bath Sleeps 6
90 90 99 99 - - - - - - 99 90 85 - - - -
31 Mtn. View Condo - Sunriver, OR Vacation Rental

31 Mtn. View Condo

Sunriver, OR
2 Bed 2 Bath Sleeps 6
99 - - - - - - 99 115 135 135 85 85 85 85 85 99
Central Lane 03 | Discover Sunriver - Sunriver, OR Vacation Rental
- - - - - - - - - - - 75 75 - - - -
Lynx Lane 08 | Discover Sunriver - Sunriver, OR Vacation Rental
125 125 135 130 - - - - 115 145 145 99 99 99 99 99 125
Cypress Lane 06 | Discover Sunriver - Sunriver, OR Vacation Rental
140 140 165 - - - - - - - - - - - - - -
Salishan Lane 02 | Discover Sunriver - Sunriver, OR Vacation Rental
- - - - - - - - - - - - - - - 195 225
2 Lark - Sunriver, OR Vacation Rental

2 Lark

Sunriver, OR
5 Bed 3.5 Bath Sleeps 12
- - - - - - - - - - - - - - - 180 265
Sisters Locust Lane Retreat - Sisters, OR Vacation Rental

Sisters Locust Lane Retreat

Sisters, OR
3 Bed 2.5 Bath Sleeps 8
99 99 130 120 - - 99 99 - - - - 99 99 - - -
Sisters: Whychus Creek Craftsman  - Sisters, OR Vacation Rental
99 99 - - - - - - - - - 90 90 90 90 90 -
Muskrat Lane 05 | Discover Sunriver - Sunriver, OR Vacation Rental
115 115 140 135 - - - - - 140 140 - - - - - -
Oxnard High Desert Retreat - Sunriver, OR Vacation Rental
- 115 - - - - - - - 155 160 99 99 99 99 99 135
Eagle Crest Huckleberry Getaway - Eagle Crest, OR Vacation Rental
140 - - - - - - - - - 195 160 160 160 160 160 225
Hickory Lane 16 | Discover Sunriver - Sunriver, OR Vacation Rental
130 130 155 - - - - - - - 160 99 99 99 99 99 125
12 Juniper - Sunriver, OR Vacation Rental

12 Juniper

Sunriver, OR
2 Bed 1 Bath Sleeps 6
70 70 - - 70 - - - 75 99 99 70 70 70 70 70 -
Eagle Crest Creekside Charmer - Eagle Crest, OR Vacation Rental
90 90 90 - - - - - - - 90 85 85 85 85 85 99
Eagle Crest Golfer's Paradise - Eagle Crest, OR Vacation Rental
125 125 140 - - - - - - - - 125 125 125 125 - -
Page 1 of 8

About Bend

Bend rated 4.8 out of 5 based on 994 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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