Language and Currency

Select your language and currency preferences for the site. Please note that all transactions will be processed in USD

Calendar View
  • Dates
    Any
  • Occupancy
    Any
    - +
    - +
    - +
  • Rooms
    Any
  • Price Range
    Any
  • Amenities
    Any
  • List
  • Map
  • Calendar

Bend Vacation Rentals

1 - 42 of 364 rentals
  PrevNext  
Sun 20 May Mon 21 May Tue 22 May Wed 23 May Thu 24 May Fri 25 May Sat 26 May Sun 27 May Mon 28 May Tue 29 May Wed 30 May Thu 31 May Fri 1 Jun Sat 2 Jun Sun 3 Jun Mon 4 Jun Tue 5 Jun
Three Giraffes - Bend, OR Vacation Rental

Three Giraffes

Bend, OR
3 Bed 3.5 Bath Sleeps 8
212 225 218 211 210 - - - - 230 250 240 270 270 270 255 259
 Sunny Daze - Bend, OR Vacation Rental

Sunny Daze

Bend, OR
3 Bed 2 Bath Sleeps 8
95 99 95 89 97 - - - 95 101 103 98 123 125 106 106 117
Heyburn House - Bend, OR Vacation Rental

Heyburn House

Bend, OR
3 Bed 2 Bath Sleeps 6
- - - - - - - - - - - 112 - - 137 133 136
West Side Wonder - Bend, OR Vacation Rental

West Side Wonder

Bend, OR
3 Bed 2.5 Bath Sleeps 6
258 259 250 243 243 - - - 242 251 259 249 280 280 279 264 268
Delaware House - Bend, OR Vacation Rental

Delaware House

Bend, OR
3 Bed 1 Bath Sleeps 6
137 146 138 125 - - - - - - - - - - - - -
Deschutes Landing at the Old Mill Riverfront - Bend, OR Vacation Rental
227 230 206 178 - - - 310 195 187 207 172 - - - - -
Studio at Pioneer - Bend, OR Vacation Rental

Studio at Pioneer

Bend, OR
0 Bed 1 Bath Sleeps 2
92 93 87 82 86 - - - 85 87 93 86 108 108 103 92 94
Riverwall  - Bend, OR Vacation Rental

Riverwall

Bend, OR
1 Bed 2 Bath Sleeps 4
95 96 87 81 92 127 - - 87 88 96 86 127 127 118 103 106
Linton Loop - Bend, OR Vacation Rental

Linton Loop

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

Best in Bend

Bend, OR
3 Bed 2.5 Bath Sleeps 6
162 173 165 160 160 - - - 158 165 172 156 - - 237 233 237
River West Cottage - Bend, OR Vacation Rental

River West Cottage

Bend, OR
3 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
The Heyburn Cottage (Downstairs) - Bend, OR Vacation Rental
113 120 114 108 111 - - - 110 114 120 106 - - 124 120 123
Mill District Cottage - Bend, OR Vacation Rental

Mill District Cottage

Bend, OR
2 Bed 1 Bath Sleeps 6
- - 81 79 87 - - - 94 95 104 96 129 129 133 114 119
Deschutes Delight - Bend, OR Vacation Rental

Deschutes Delight

Bend, OR
1 Bed 2 Bath Sleeps 4
- - - 69 78 - - - 87 88 96 86 127 127 118 103 106
Parkview at Pioneer - Bend, OR Vacation Rental

Parkview at Pioneer

Bend, OR
1 Bed 2 Bath Sleeps 4
105 106 97 90 97 - - 171 101 98 106 95 140 140 130 113 111
Cascade Lodge  - Bend, OR Vacation Rental

Cascade Lodge

Bend, OR
4 Bed 2.5 Bath Sleeps 10
- - - - - - - - - - - - - - - - -
Riverside Park - Bend, OR Vacation Rental

Riverside Park

Bend, OR
1 Bed 2 Bath Sleeps 4
- - 83 81 92 127 - - 87 88 96 86 108 - - 87 90
Riverwalk - Bend, OR Vacation Rental

Riverwalk

Bend, OR
1 Bed 1 Bath Sleeps 4
- - - - - - - 154 110 107 114 107 134 134 127 114 117
Summer Shade Sanctuary - Bend, OR Vacation Rental

Summer Shade Sanctuary

Bend, OR
3 Bed 2 Bath Sleeps 8
- 135 128 117 129 - - - 128 123 - - - - 168 151 157
The Heyburn Cottage (Upstairs) - Bend, OR Vacation Rental
139 - - - - - - - 136 140 148 138 167 166 161 148 151
Rock Bluff Retreat - Bend, OR Vacation Rental

Rock Bluff Retreat

Bend, OR
3 Bed 2 Bath Sleeps 6
176 177 168 162 165 228 214 223 162 168 175 169 184 - - - -
Spring Breeze - Bend, OR Vacation Rental

Spring Breeze

Bend, OR
1 Bed 2 Bath Sleeps 4
95 96 87 77 - - - - 87 88 96 86 140 140 130 113 117
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)
261 265 235 201 - - - - 211 213 238 195 - - 278 246 257
Gleneden Getaway - Bend, OR Vacation Rental

Gleneden Getaway

Bend, OR
4 Bed 2.5 Bath Sleeps 8
- 167 - - - - - - - - - 151 - - 121 128 128
Russet Appeal at Pioneer - Bend, OR Vacation Rental

Russet Appeal at Pioneer

Bend, OR
1 Bed 2 Bath Sleeps 4
95 96 87 81 87 - - 122 82 75 - - - - 114 - -
River Wild at Mt. Bachelor Village - Bend, OR Vacation Rental
- 180 156 141 161 - - - 180 181 192 - - - - - -
Mt Bachelor Village Ski House # 219 - Bend, OR Vacation Rental
83 90 87 84 81 - - - 85 85 - - - 106 107 - -
Shanti River House - Near La Pine State Park - Bend, OR Vacation Rental
- - 126 126 154 - - - 165 176 176 171 213 217 183 182 202
Blue Sage Bunkhouse - Bend, OR Vacation Rental

Blue Sage Bunkhouse

Bend, OR
1 Bed 1 Bath Sleeps 3 (2 Adults Max)
53 57 55 54 52 - - 83 57 57 57 51 - - - - 54
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
Seventh Mountain Luxury - Bend, OR Vacation Rental

Seventh Mountain Luxury

Bend, OR
1 Bed 1 Bath Sleeps 4
- 88 91 89 85 - - - - 84 - - - - 108 105 104
 Mt Bachelor Delight - Bend, OR Vacation Rental

Mt Bachelor Delight

Bend, OR
2 Bed 1 Bath Sleeps 6
- 108 97 88 97 - - - 113 115 127 105 - - - - -
Mt Bachelor Village Ski House  #244 - Bend, OR Vacation Rental
- 85 85 85 - - - - - - 85 - - - 87 85 85
River Wild  - Bend, OR Vacation Rental

River Wild

Bend, OR
3 Bed 2.5 Bath Sleeps 9
- 200 - - - - - - 200 200 200 200 - - - - 200
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
Mt Bachelor Village Ski House # 262 - Bend, OR Vacation Rental
- 95 95 95 95 - - - 95 95 95 95 - - 109 104 103
River Landing Suite #1 - Bend, OR Vacation Rental

River Landing Suite #1

Bend, OR
3 Bed 1.5 Bath Sleeps 8
- 89 89 89 89 - - - 90 89 - - - - 117 107 111
River Landing Suite #2 - Bend, OR Vacation Rental

River Landing Suite #2

Bend, OR
2 Bed 1.5 Bath Sleeps 6
105 106 91 - - - - - - 88 - - - - - - 96
Blue Sage Ranch - Bend, OR Vacation Rental

Blue Sage Ranch

Bend, OR
2 Bed 2 Bath Sleeps 4
- - - - - - - - - 119 139 115 - - - - -
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
213 - - - - - - - 184 191 201 181 - - 222 215 220
Page 1 of 9

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