Vacation Rentals in Bend, Oregon

50 Properties Available

Sleeps 100! 20 Modern Units, 50 BDRs, Near DT Bend Private vacation home
Sleeps 100! 20 Modern Units, 50 BDRs, Near DT Bend
$9876 / night
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Luxury 7 Br, 7.5 Ba Home. Great for Retreats and Family Gatherings! Private vacation home
Luxury 7 Br, 7.5 Ba Home. Great for Retreats and Family Gatherings!
$2573 / night
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Log Cabin in the Pines with 3 Kings + Bunks, Bikes, AC, Games and Hot Tub - WDK09 Private vacation home
Log Cabin in the Pines with 3 Kings + Bunks, Bikes, AC, Games and Hot Tub - WDK09
$1746 / night
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Caldera Springs Escape with Access to Exclusive Golf Private vacation home
Caldera Springs Escape with Access to Exclusive Golf
$1739 / night
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Lakeside Lodge with Access to Forest House Cabin
Lakeside Lodge with Access to Forest House
$1528 / night
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Bend ~ 24-hr staff ~ gorgeous kitchen ~ comfy beds ~ W/D ~ Cascade Lakes ~ ? Private vacation home
Bend ~ 24-hr staff ~ gorgeous kitchen ~ comfy beds ~ W/D ~ Cascade Lakes ~ ?
$1487 / night
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NEW BEND HOME ~ great for groups ~ resort pool ~ concert shuttle ~ W/D ~ ? Private vacation home
NEW BEND HOME ~ great for groups ~ resort pool ~ concert shuttle ~ W/D ~ ?
$1487 / night
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Lakeside Retreat with Access to Forest House Cabin
Lakeside Retreat with Access to Forest House
$1460 / night
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Forest View Lodge with Access to Forest House Private vacation home
Forest View Lodge with Access to Forest House
$1369 / night
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Risa Cabin: Full Lodge | Lake, Hot Tub, 9 Acres Cabin
Risa Cabin: Full Lodge | Lake, Hot Tub, 9 Acres
$1264 / night
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5-Star Caldera Luxury House - 3 King Suites + Chef Kitchen + Hot Tub + Game Loft Private vacation home
5-Star Caldera Luxury House - 3 King Suites + Chef Kitchen + Hot Tub + Game Loft
$1247 / night
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Family Fun Lodge with Access to Exclusive Golf Private vacation home
Family Fun Lodge with Access to Exclusive Golf
$1181 / night
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2 Units | Deck, Hot Tub, Minutes to Old Bend | 1212 Skyline Ranch by AvantStay Private vacation home
2 Units | Deck, Hot Tub, Minutes to Old Bend | 1212 Skyline Ranch by AvantStay
$1167 / night
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2 Units | Minutes to Old Bend, Deck + Hot Tub | 1204 Skyline Ranch by AvantStay Private vacation home
2 Units | Minutes to Old Bend, Deck + Hot Tub | 1204 Skyline Ranch by AvantStay
$1167 / night
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Near Old Bend, Hot Tub | 2 Units - Family | Aerie Private vacation home
Near Old Bend, Hot Tub | 2 Units - Family | Aerie
$1163 / night
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2 Units | Minutes to Downtown Bend | Hot Tub | 1208 Skyline Ranch by AvantStay Private vacation home
2 Units | Minutes to Downtown Bend | Hot Tub | 1208 Skyline Ranch by AvantStay
$1147 / night
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2 Units | Minutes to Old Bend | Deck + Hot Tub | 1216 Skyline Ranch by AvantStay Private vacation home
2 Units | Minutes to Old Bend | Deck + Hot Tub | 1216 Skyline Ranch by AvantStay
$1134 / night
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RELAX! Soaking tub ~ fire place ~ hot tub ~ resort pool + amenities ~ Bend ~ ? Private vacation home
RELAX! Soaking tub ~ fire place ~ hot tub ~ resort pool + amenities ~ Bend ~ ?
$1130 / night
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Luxurious Estate among the Pines w\/ Hot Tub, EV Charger & so much MORE! Private vacation home
Luxurious Estate among the Pines w\/ Hot Tub, EV Charger & so much MORE!
$1124 / night
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Seventh Mountain Resort - Cute 3 Bedroom Condo with Fireplace - 823 Condo
Seventh Mountain Resort - Cute 3 Bedroom Condo with Fireplace - 823
$1070 / night
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Sunstone at Caldera Springs with Quarry Recreation Private vacation home
Sunstone at Caldera Springs with Quarry Recreation
$1068 / night
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Located on Bend's most sought after historic district street, provides the perfe Private vacation home
Located on Bend's most sought after historic district street, provides the perfe
$1051 / night
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Caldera Springs Lodge with Access to Forest House Private vacation home
Caldera Springs Lodge with Access to Forest House
$1047 / night
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Riverfront Lodge great setting, walk to downtown! Lodge
Riverfront Lodge great setting, walk to downtown!
$1044 / night
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Four Seasons Luxury Private vacation home
Four Seasons Luxury
$1039 / night
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Caldera Lodge with Access to Forest House Private vacation home
Caldera Lodge with Access to Forest House
$981 / night
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Midtown Mid-Century w\/ Pool & Hot Tub Near Downtown Private vacation home
Midtown Mid-Century w\/ Pool & Hot Tub Near Downtown
$976 / night
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Private get away Spacious, sleeps 18 ..large game room Cabin
Private get away Spacious, sleeps 18 ..large game room
$965 / night
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Caldera Springs Luxury home! Sleeps 12 Private vacation home
Caldera Springs Luxury home! Sleeps 12
$964 / night
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Skyline Lodge, Gorgeous Setting, Walk to Downtown! Lodge
Skyline Lodge, Gorgeous Setting, Walk to Downtown!
$916 / night
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20 acres private ranch with Mountain View’s Private vacation home
20 acres private ranch with Mountain View’s
$906 / night
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SUNNY VACAY ~ 24-hr staff ~ south views ~ BBQ ~ ? ~ hot tub ~ Bend Private vacation home
SUNNY VACAY ~ 24-hr staff ~ south views ~ BBQ ~ ? ~ hot tub ~ Bend
$900 / night
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Lakeside Retreat with Access to Exclusive Golf Cabin
Lakeside Retreat with Access to Exclusive Golf
$890 / night
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Hyde House Retreat - Pickleball & Basketball Private vacation home
Hyde House Retreat - Pickleball & Basketball
$875 / night
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Stunning Historic Home on Bend's West Side Private vacation home
Stunning Historic Home on Bend's West Side
$865 / night
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Spacious Sunriver Getaway with Access to Forest House Private vacation home
Spacious Sunriver Getaway with Access to Forest House
$857 / night
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Tranquil Retreat with Access to Forest House Cabin
Tranquil Retreat with Access to Forest House
$843 / night
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Sunriver Getaway with Access to Forest House Private vacation home
Sunriver Getaway with Access to Forest House
$835 / night
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Caldera Cabin with Access to Foresthouse Cabin
Caldera Cabin with Access to Foresthouse
$784 / night
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Trailmere Escape with Access to Forest House Private vacation home
Trailmere Escape with Access to Forest House
$784 / night
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Luxe Family Retreat with Access to Forest House Cabin
Luxe Family Retreat with Access to Forest House
$769 / night
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Caldera Escape with Access to Exclusive Golf Cabin
Caldera Escape with Access to Exclusive Golf
$765 / night
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Lakefront Cabin with Access to Exclusive Golf Cabin
Lakefront Cabin with Access to Exclusive Golf
$765 / night
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Luxury Caldera Retreat with Access to Forest House Cabin
Luxury Caldera Retreat with Access to Forest House
$765 / night
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Sable Rock Lodge with Access to Exclusive Golf Private vacation home
Sable Rock Lodge with Access to Exclusive Golf
$765 / night
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Big Sky by AvantStay | Beautiful Mountain Home w\/ Great Views! Private vacation home
Big Sky by AvantStay | Beautiful Mountain Home w\/ Great Views!
$765 / night
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Lakeside Cabin with Access to Exclusive Golf Cabin
Lakeside Cabin with Access to Exclusive Golf
$760 / night
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Lakeview Escape with Access to Exclusive Golf Cabin
Lakeview Escape with Access to Exclusive Golf
$759 / night
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Luxury Cabin with Access to Forest House Cabin
Luxury Cabin with Access to Forest House
$759 / night
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Luxury Cabin with Access to Exclusive Golf Cabin
Luxury Cabin with Access to Exclusive Golf
$750 / night
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