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Bend Vacation Rentals

1 - 42 of 365 rentals
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Three Giraffes - Bend, OR Vacation Rental

Three Giraffes

Bend, OR
3 Bed 3.5 Bath Sleeps 8
200 198 - - - - - - - 270 270 256 242 245 253 254 284
Heyburn House - Bend, OR Vacation Rental

Heyburn House

Bend, OR
3 Bed 2 Bath Sleeps 6
- - - - - - - - 113 - - 130 126 129 135 129 -
River West Cottage - Bend, OR Vacation Rental

River West Cottage

Bend, OR
3 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Spring Breeze - Bend, OR Vacation Rental

Spring Breeze

Bend, OR
1 Bed 2 Bath Sleeps 4
65 - - - - - - - - 140 140 123 107 111 119 121 156
West Side Wonder - Bend, OR Vacation Rental

West Side Wonder

Bend, OR
3 Bed 2.5 Bath Sleeps 6
207 205 - - - 243 251 260 251 280 280 265 251 254 262 263 294
Studio at Pioneer - Bend, OR Vacation Rental

Studio at Pioneer

Bend, OR
0 Bed 1 Bath Sleeps 2
69 73 - - - 86 87 94 87 108 108 97 87 89 95 96 118
 Sunny Daze - Bend, OR Vacation Rental

Sunny Daze

Bend, OR
3 Bed 2 Bath Sleeps 8
89 89 - - - 95 101 101 97 123 126 101 100 111 125 125 140
The Heyburn Cottage (Downstairs) - Bend, OR Vacation Rental
102 105 - - - 111 114 121 107 - - 117 114 116 122 116 -
Deschutes Delight - Bend, OR Vacation Rental

Deschutes Delight

Bend, OR
1 Bed 2 Bath Sleeps 4
- 74 - - - 78 75 - - - 108 112 97 101 109 110 142
Cascade Lodge  - Bend, OR Vacation Rental

Cascade Lodge

Bend, OR
4 Bed 2.5 Bath Sleeps 10
- - - - - - - - - - - - - - 134 - -
Deschutes Landing at the Old Mill Riverfront - Bend, OR Vacation Rental
151 - - - 293 198 187 209 176 - - - - - - - -
Linton Loop - Bend, OR Vacation Rental

Linton Loop

Bend, OR
4 Bed 2.5 Bath Sleeps 8
- - - - - - - - - 190 - - - - - - -
Riverwall  - Bend, OR Vacation Rental

Riverwall

Bend, OR
1 Bed 2 Bath Sleeps 4
76 87 - - - 88 88 96 87 127 127 112 97 101 109 110 142
Summer Shade Sanctuary - Bend, OR Vacation Rental

Summer Shade Sanctuary

Bend, OR
3 Bed 2 Bath Sleeps 8
111 122 - - - 130 123 - - - - 159 143 149 163 157 -
Riverside Park - Bend, OR Vacation Rental

Riverside Park

Bend, OR
1 Bed 2 Bath Sleeps 4
- 87 120 - - 78 79 82 - - - - 83 86 - - 135
Riverwalk - Bend, OR Vacation Rental

Riverwalk

Bend, OR
1 Bed 1 Bath Sleeps 4
- - - - 146 116 110 116 110 134 134 120 108 111 117 119 146
Rock Bluff Retreat - Bend, OR Vacation Rental

Rock Bluff Retreat

Bend, OR
3 Bed 2 Bath Sleeps 6
- - 216 202 200 177 171 178 171 184 - - - - - - -
Parkview at Pioneer - Bend, OR Vacation Rental

Parkview at Pioneer

Bend, OR
1 Bed 2 Bath Sleeps 4
76 82 - - 162 103 98 107 97 140 140 123 107 105 - - -
River Wild at Mt. Bachelor Village - Bend, OR Vacation Rental
128 150 - - - 197 192 199 - - - - - - - - -
Gleneden Getaway - Bend, OR Vacation Rental

Gleneden Getaway

Bend, OR
4 Bed 2.5 Bath Sleeps 8
- - - - - - - - - - - 115 122 122 122 115 -
Best in Bend - Bend, OR Vacation Rental

Best in Bend

Bend, OR
3 Bed 2.5 Bath Sleeps 6
149 151 - - - 163 168 174 159 - - 224 221 225 233 235 260
Amazing Luxury Downtown Old Mill Home - Bend, OR Vacation Rental

Amazing Luxury Downtown Old Mill Home

Bend, OR
2 Bed 2 Bath Sleeps 8 (6 Adults Max)
190 - - - - 215 213 241 200 - - 216 191 200 220 213 -
The Heyburn Cottage (Upstairs) - Bend, OR Vacation Rental
- - - - - 123 126 134 119 - - 130 126 129 127 - -
Russet Appeal at Pioneer - Bend, OR Vacation Rental

Russet Appeal at Pioneer

Bend, OR
1 Bed 2 Bath Sleeps 4
69 74 - - 116 83 75 - - - - 108 - - - - -
Mill District Cottage - Bend, OR Vacation Rental

Mill District Cottage

Bend, OR
2 Bed 1 Bath Sleeps 6
74 81 - - - 101 100 107 100 129 129 126 108 113 122 124 123
Charming Old Mill Homestead - Bend, OR Vacation Rental

Charming Old Mill Homestead

Bend, OR
4 Bed 2.5 Bath Sleeps 10
- - - - - - 185 185 185 - - - 185 185 185 - -
Mt Bachelor Village Ski House # 219 - Bend, OR Vacation Rental
79 76 - - - 85 85 - - - 123 101 - - 83 - -
Seventh Mountain Luxury - Bend, OR Vacation Rental

Seventh Mountain Luxury

Bend, OR
1 Bed 1 Bath Sleeps 4
79 80 - - - - 84 - - - - 102 101 99 105 107 143
Blue Sage Bunkhouse - Bend, OR Vacation Rental

Blue Sage Bunkhouse

Bend, OR
1 Bed 1 Bath Sleeps 3 (2 Adults Max)
- - - - 79 57 57 57 52 - - - - 51 58 56 -
Shanti River House - Near La Pine State Park - Bend, OR Vacation Rental
111 146 - - - 165 176 177 177 213 219 175 173 191 218 218 243
 Mt Bachelor Delight - Bend, OR Vacation Rental

Mt Bachelor Delight

Bend, OR
2 Bed 1 Bath Sleeps 6
78 92 - - - 104 103 116 97 - - - - - - - -
River Wild  - Bend, OR Vacation Rental

River Wild

Bend, OR
3 Bed 2.5 Bath Sleeps 9
- - - - - 200 200 200 200 - - - - 200 200 203 216
Mt Bachelor Village Ski House  #244 - Bend, OR Vacation Rental
85 - - - - - - 85 - - - 85 85 85 85 85 -
Mt Bachelor Village Ski House # 262 - Bend, OR Vacation Rental
95 95 - - - 95 95 95 95 - - 95 95 95 95 95 -
Log Cabin Riverfront Getaway - Bend, OR Vacation Rental

Log Cabin Riverfront Getaway

Bend, OR
2 Bed 2 Bath Sleeps 6
250 250 250 - - 250 250 250 250 250 250 250 250 250 250 250 250
Delaware House - Bend, OR Vacation Rental

Delaware House

Bend, OR
3 Bed 1 Bath Sleeps 6
116 - - - - - - - - - - - - - - - -
River Landing Suite #1 - Bend, OR Vacation Rental

River Landing Suite #1

Bend, OR
3 Bed 1.5 Bath Sleeps 8
89 89 - - - 91 89 - - - - 111 101 105 114 110 -
River Landing Suite #2 - Bend, OR Vacation Rental

River Landing Suite #2

Bend, OR
2 Bed 1.5 Bath Sleeps 6
- - - - - - 88 - - - - - - 91 - - -
Blue Sage Ranch - Bend, OR Vacation Rental

Blue Sage Ranch

Bend, OR
2 Bed 2 Bath Sleeps 4
- - - - - - 119 140 118 - - - - - - - -
Bend Mountain View Retreat - Bend, OR Vacation Rental

Bend Mountain View Retreat

Bend, OR
4 Bed 3.5 Bath Sleeps 10
- - - - - - - - - - - - - - - - -
Bend Traditional w/Hot Tub & Biking trails - Bend, OR Vacation Rental
- - - - - - - - - - - - - - - - -
The Heyburn Cottage (Upstairs & Downstairs) - Bend, OR Vacation Rental
- - - - - 192 196 204 185 - - 198 192 196 194 - -
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About Bend

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, our Bend vacation rentals 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 rental 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, 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.

Photo Credit: Gordon-Shukwit via Flickr