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Bend Holiday Rentals

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557 rentals in Bend.
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Tumalo Pines, holiday rental in Bend

Tumalo Pines

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Mins to the Heart of Sunriver! Bikes & Ping Pong, Patio w/ Grill, Fenced in Back, holiday rental in Bend

Mins to the Heart of Sunriver! Bikes & Ping Pong, Patio w/ Grill, Fenced in Back

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Charming Bungalow, Location, Location, Location!, holiday rental in Bend

Charming Bungalow, Location, Location, Location!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Hemmingway *30 Day Min Stay, holiday rental in Bend

Hemmingway *30 Day Min Stay

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Mt Bachelor Village -Top floor with 2 Queen beds +, holiday rental in Bend

Mt Bachelor Village -Top floor with 2 Queen beds +

1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps
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Upscale townhouse w/ amazing location - walk to breweries & the Amphitheater!, holiday rental in Bend

Upscale townhouse w/ amazing location - walk to breweries & the Amphitheater!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Downtown Riverfront Cottage, holiday rental in Bend

Downtown Riverfront Cottage

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Craftsman Bungalow - Walk Everywhere! Only 2 Blocks To Downtown, holiday rental in Bend

Craftsman Bungalow - Walk Everywhere! Only 2 Blocks To Downtown

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Check INN Seventh Mountain Comfort, holiday rental in Bend

Check INN Seventh Mountain Comfort

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Bend Country Cabins/ Private Setting Pet Friendly - $90/night for 2  plus nights, holiday rental in Bend

Bend Country Cabins/ Private Setting Pet Friendly - $90/night for 2 plus nights

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Stunning Aquila Lodges at Sunriver Retreat w/ Private Hot Tub, holiday rental in Bend

Stunning Aquila Lodges at Sunriver Retreat w/ Private Hot Tub

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Great condo w/2 decks,  near the slopes - city view (3rd bedroom option), holiday rental in Bend

Great condo w/2 decks, near the slopes - city view (3rd bedroom option)

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ponderosa Paradise with a million dollar view, holiday rental in Bend

Ponderosa Paradise with a million dollar view

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Happiness is just Around the Bend, Caldera Springs Resort Sunriver, Bend Oregon, holiday rental in Bend

Happiness is just Around the Bend, Caldera Springs Resort Sunriver, Bend Oregon

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Amazing West Side  * 2 King Suites * Walk Everywhere  * 8 Person Hot Tub, holiday rental in Bend

Amazing West Side * 2 King Suites * Walk Everywhere * 8 Person Hot Tub

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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RiverWild Mt. Bach Village  PRIVATE HOT TUB Wi/Fi A/C, holiday rental in Bend

RiverWild Mt. Bach Village PRIVATE HOT TUB Wi/Fi A/C

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Truly one of the Best Homes on the River! Safe & Open!!!, holiday rental in Bend

Truly one of the Best Homes on the River! Safe & Open!!!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Immaculate & Secluded downtown Bend Cottage- Summer filling fast, holiday rental in Bend

Immaculate & Secluded downtown Bend Cottage- Summer filling fast

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Old Mill Getaway At Deschutes Landing, holiday rental in Bend

Old Mill Getaway At Deschutes Landing

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Epic Riverfront Estate. Iconic Bend home. Walk everywhere. Recreate on river. 4, holiday rental in Bend

Epic Riverfront Estate. Iconic Bend home. Walk everywhere. Recreate on river. 4

6 bedrooms
4 bathrooms
Sleeps 10
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Fantastic West Side! Drake Park. Hot Tub. Weeknight Special $195 night., holiday rental in Bend

Fantastic West Side! Drake Park. Hot Tub. Weeknight Special $195 night.

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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20 acres private ranch 5 miles east of bend, holiday rental in Bend

20 acres private ranch 5 miles east of bend

7 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Historic Belle Millhouse in Bend, OR.  Walk to Downtown.vrbo, holiday rental in Bend

Historic Belle Millhouse in Bend, OR. Walk to Downtown.vrbo

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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River View Contemporary Vacation Townhouse, holiday rental in Bend

River View Contemporary Vacation Townhouse

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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River View Condo, Close To Town/Mountain, New Private Hot Tub, holiday rental in Bend

River View Condo, Close To Town/Mountain, New Private Hot Tub

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Amazing West Side * 2 King Suites * Walk Everywhere  * 8 Person Hot Tub, holiday rental in Bend

Amazing West Side * 2 King Suites * Walk Everywhere * 8 Person Hot Tub

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Pet Friendly, luxury log cabin with hot tub near Sunriver!, holiday rental in Bend

Pet Friendly, luxury log cabin with hot tub near Sunriver!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Downtown by the River! Cozy, Contemporary Cottage, holiday rental in Bend

Downtown by the River! Cozy, Contemporary Cottage

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Executive Lodge up in the West Hills and is 2 miles from downtown Bend., holiday rental in Bend

The Executive Lodge up in the West Hills and is 2 miles from downtown Bend.

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Family-Friendly Luxury Retreat Featured On 2015 Tour Of Homes! DCCA#1253, holiday rental in Bend

Family-Friendly Luxury Retreat Featured On 2015 Tour Of Homes! DCCA#1253

4 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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# 4 Backwoods Lodge 6BR/6BA SHARC, by Village, LD Wknd 4th nt free, holiday rental in Bend

# 4 Backwoods Lodge 6BR/6BA SHARC, by Village, LD Wknd 4th nt free

6 bedrooms
6 bathrooms
Sleeps 15
Match: Sleeps
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Beautiful inside, amazing outside, bikes, kayaks, SHARC, holiday rental in Bend

Beautiful inside, amazing outside, bikes, kayaks, SHARC

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Westside Wonderful!  Walk downtown - peace & quiet and pet friendly, holiday rental in Bend

Westside Wonderful! Walk downtown - peace & quiet and pet friendly

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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AWESOME Unobstructed Deschutes RIVER VIEW!  Downtown Bend, holiday rental in Bend

AWESOME Unobstructed Deschutes RIVER VIEW! Downtown Bend

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cute Westside Craftsman, Walk to Downtown, Large Garage, Cruiser Bikes!, holiday rental in Bend

Cute Westside Craftsman, Walk to Downtown, Large Garage, Cruiser Bikes!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Downtown Bungalow, Gourmet Kitchen, 2BR/1.5BA, holiday rental in Bend

Downtown Bungalow, Gourmet Kitchen, 2BR/1.5BA

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Stay In The Heart Of Bend, Walk Everywhere!  New Hot Tub!, holiday rental in Bend

Stay In The Heart Of Bend, Walk Everywhere! New Hot Tub!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Location! Location! BUNGALOW at DESCHUTES DUNES River & Beach, holiday rental in Bend

Location! Location! BUNGALOW at DESCHUTES DUNES River & Beach

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Beautiful 5 bdrm! Hot tub! River! Bring the dogs! 5 minutes to Sunriver Village!, holiday rental in Bend

Beautiful 5 bdrm! Hot tub! River! Bring the dogs! 5 minutes to Sunriver Village!

5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Bend Getaway in RiverWild-Walk to Deschutes River and Old Mill District, holiday rental in Bend

Bend Getaway in RiverWild-Walk to Deschutes River and Old Mill District

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Family Vacation Home. 5 Bedrooms, Wi-Fi, Westside, 5mins from Old Mill, holiday rental in Bend

Beautiful Family Vacation Home. 5 Bedrooms, Wi-Fi, Westside, 5mins from Old Mill

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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This waterfront home on Mirror Pond is steps away from Downtown Bend, holiday rental in Bend

This waterfront home on Mirror Pond is steps away from Downtown Bend

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spectacular Luxury Old Mill District Townhouse Walking Distance To River Walk, holiday rental in Bend

Spectacular Luxury Old Mill District Townhouse Walking Distance To River Walk

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Amazing West Side - Walk Everywhere - Dog Friendly, holiday rental in Bend

Amazing West Side - Walk Everywhere - Dog Friendly

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Great River Front Vacation Home in Sunriver with Hot Tub! Pet Friendly DCCA#1432, holiday rental in Bend

Great River Front Vacation Home in Sunriver with Hot Tub! Pet Friendly DCCA#1432

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Awesome location! Next to river, close to downtown.  Walk everywhere!, holiday rental in Bend

Awesome location! Next to river, close to downtown. Walk everywhere!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxury Home yet Family-Friendly! It's all about creating memories!, holiday rental in Bend

Luxury Home yet Family-Friendly! It's all about creating memories!

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Serene Sunriver Home, Newly Remodeled!, holiday rental in Bend

Serene Sunriver Home, Newly Remodeled!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious home! Arcade, 2 Masters-A/C-SHARC-Hot Tub-Sauna-Great Location, holiday rental in Bend

Spacious home! Arcade, 2 Masters-A/C-SHARC-Hot Tub-Sauna-Great Location

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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DOWNTOWN RIVERFRONT HOME W/ RIVER ACCESS, BEST LOCATION,  2 MASTER SUITES!, holiday rental in Bend

DOWNTOWN RIVERFRONT HOME W/ RIVER ACCESS, BEST LOCATION, 2 MASTER SUITES!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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