Home Vacation Rentals By Owner In Bennington, VT

Showing 20 Of 33 Vacation Rentals
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Exceptional(17)

$285.6

/ Nightly
Cottage

Lake life at Woodford Cottage

Bennington, Vermont, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(8)

$161.06

/ Nightly
Apartment

Cozy Loft steps from VT Downtown

Bennington, Vermont, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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Exceptional(2)

$363.44

/ Nightly
Cabin

Charming 2 bath/3 bed cabin in Woodford

Woodford, Vermont, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(36)

$290.68

/ Nightly
Private Vacation Home

Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Bennington, Vermont, United States

Bed 3

Bed

Bath 1

Bath

Sleep 8

Sleeps
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Exceptional(17)

$411.46

/ Nightly
Private Vacation Home

One of a kind cozy Renovated VT Barn- where Family, Friends, Couples gather

Shaftsbury, Vermont, United States

Bed 3

Bed

Bath 1

Bath

Sleep 8

Sleeps
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Exceptional(1)

$253.68

/ Nightly
Private Vacation Home

< 1 Mi to Historic District! Retreat in Bennington

Bennington, Vermont, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(11)

$369.16

/ Nightly
Apartment

Luxury Living High Above the Center of Town.

Bennington, Vermont, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(76)

$894.32

/ Nightly
Private Vacation Home

Karin's Place VT: Secluded post and beam with private pool, sauna, & playground

Bennington, Vermont, United States

Bed 5

Bed

Bath 2

Bath

Sleep 12

Sleeps
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$251.11

/ Nightly
Private Vacation Home

Tranquil 3-bedroom farmhouse in charming Woodford perfect for relaxing

Woodford, Vermont, United States

Bed 3

Bed

Bath 2

Bath

Sleep 5

Sleeps
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$355.38

/ Nightly
Agritourism

1865 Bennington Farmhouse: Mountain, Monument & Meadow views & Charm

Bennington, Vermont, United States

Bed 3

Bed

Bath 2

Bath

Sleep 5

Sleeps
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Bed & Breakfast

Victorian mansions Coach Room with Breakfast

Bennington, Vermont, United States

Bed 1

Bed

Bath 1

Bath

Sleep 1

Sleeps
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Exceptional(87)

$269.92

/ Nightly
Cottage

Perfect for a peaceful get away in clean fresh Vermont air!

Woodford, Vermont, United States

Bed 4

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(10)

$451.36

/ Nightly
Cabin

Cozy, welcoming, 3-bedroom cabin abutting the Green Mountain National Forest!

Woodford, Vermont, United States

Bed 3

Bed

Bath 2

Bath

Sleep 7

Sleeps
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$404.7

/ Nightly
Private Vacation Home

The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

Woodford, Vermont, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(13)

$221.65

/ Nightly
Apartment

Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown

Bennington, Vermont, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(39)

$315.84

/ Nightly
Cabin

Lakeview Cabin in the Mountains

Woodford, Vermont, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(20)

$311.82

/ Nightly
Apartment

Green Mountain Getaway

Bennington, Vermont, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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$261.08

/ Nightly
Apartment

Spacious 2nd floor apartment steps from popular corner market.

Bennington, Vermont, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(10)

$472.64

/ Nightly
Private Vacation Home

Meme's High Mountain Lake House

Woodford, Vermont, United States

Bed 3

Bed

Bath 2

Bath

Sleep 11

Sleeps
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Exceptional(18)

$403.2

/ Nightly
Cottage

Bright 3-Bedroom Historical Cottage w/ pool table

Bennington, Vermont, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Home Most popular vacation rentals in Bennington

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Exceptional(18)

$403.20

/ Nightly
Cottage

Bright 3-Bedroom Historical Cottage w/ pool table

Bennington, Vermont, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(18)

$221.65

/ Nightly
Apartment

Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown

Bennington, Vermont, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(18)

$253.68

/ Nightly
Private vacation home

< 1 Mi to Historic District! Retreat in Bennington

Bennington, Vermont, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(18)

$269.92

/ Nightly
Cottage

Perfect for a peaceful get away in clean fresh Vermont air!

Woodford, Vermont, United States

Bed 4

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(18)

$280.56

/ Nightly
Cottage

Bright airy cottage with lakeview in Woodford Vt - perfect vacation getaway

Woodford, Vermont, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(18)

$315.84

/ Nightly
Cabin

Lakeview Cabin in the Mountains

Woodford, Vermont, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(18)

$367.92

/ Nightly
Private vacation home

NEW!! Renovated historic 3 BR 2 full BA. Walkable to downtown. Restaurants/Shops

Bennington, Vermont, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(18)

$369.16

/ Nightly
Apartment

Luxury Living High Above the Center of Town.

Bennington, Vermont, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(18)

$672.56

/ Nightly
Cabin

Breathtaking Mtn Views: Stylish Rustic Retreat!

Bennington, Vermont, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(18)

$663.72

/ Nightly
Cabin

Cozy Cabin & Fun-Filled Barn VAST Access Near Mt Snow & Prospect Mt

Woodford, Vermont, United States

Bed 4

Bed

Bath 1

Bath

Sleep 10

Sleeps

Most Popular Cities in Vermont