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Bennington Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
49 rentals in Bennington.
Cozy Trailside Retreat, vacation rental in Bennington
Cozy Trailside Retreat, vacation rental in Bennington
Cozy Trailside Retreat, vacation rental in Bennington

Cozy Trailside Retreat

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The following properties within 20 miles of Bennington match all your filters:
Lake Front Retreat With Deep Water Dock, vacation rental in Bennington
Lake Front Retreat With Deep Water Dock, vacation rental in Bennington
Lake Front Retreat With Deep Water Dock, vacation rental in Bennington

Lake Front Retreat With Deep Water Dock

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning & Scenic 1BR w/ Resort Pool and Close to Ski Area, vacation rental in Bennington
Stunning & Scenic 1BR w/ Resort Pool and Close to Ski Area, vacation rental in Bennington
Stunning & Scenic 1BR w/ Resort Pool and Close to Ski Area, vacation rental in Bennington

Stunning & Scenic 1BR w/ Resort Pool and Close to Ski Area

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Affiliated with FlipKey
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!, vacation rental in Bennington
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!, vacation rental in Bennington
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!, vacation rental in Bennington

Spacious Estate With Mtn Views! Private Setting, Great Family Home!!

Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Luxury Hot Tub Getaway, vacation rental in Bennington
Luxury Hot Tub Getaway, vacation rental in Bennington
Luxury Hot Tub Getaway, vacation rental in Bennington

Luxury Hot Tub Getaway

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Lemon Drop Cottage a private cottage getaway, vacation rental in Bennington
Lemon Drop Cottage a private cottage getaway, vacation rental in Bennington
Lemon Drop Cottage a private cottage getaway, vacation rental in Bennington

Lemon Drop Cottage a private cottage getaway

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Room 01 - Queen Room, vacation rental in Bennington
Room 01 - Queen Room, vacation rental in Bennington
Room 01 - Queen Room, vacation rental in Bennington

Room 01 - Queen Room

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Family Cottage On Pristine Lake Nubanusit, vacation rental in Bennington
Family Cottage On Pristine Lake Nubanusit, vacation rental in Bennington
Family Cottage On Pristine Lake Nubanusit, vacation rental in Bennington

Family Cottage On Pristine Lake Nubanusit

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Cozy Tiny House on Main Street.  Fully Renovated. *NO CLEANING FEE*, vacation rental in Bennington
Cozy Tiny House on Main Street.  Fully Renovated. *NO CLEANING FEE*, vacation rental in Bennington
Cozy Tiny House on Main Street.  Fully Renovated. *NO CLEANING FEE*, vacation rental in Bennington

Cozy Tiny House on Main Street. Fully Renovated. *NO CLEANING FEE*

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Room 01A - Twin room, vacation rental in Bennington
Room 01A - Twin room, vacation rental in Bennington
Room 01A - Twin room, vacation rental in Bennington

Room 01A - Twin room

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Rustic Waterfront Cottage w/ Fire Pit & Kayaks, vacation rental in Bennington
Rustic Waterfront Cottage w/ Fire Pit & Kayaks, vacation rental in Bennington
Rustic Waterfront Cottage w/ Fire Pit & Kayaks, vacation rental in Bennington

Rustic Waterfront Cottage w/ Fire Pit & Kayaks

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Room 01B - Queen Room, vacation rental in Bennington
Room 01B - Queen Room, vacation rental in Bennington
Room 01B - Queen Room, vacation rental in Bennington

Room 01B - Queen Room

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Cottage Lake Nubanusit, vacation rental in Bennington
Cottage Lake Nubanusit, vacation rental in Bennington
Cottage Lake Nubanusit, vacation rental in Bennington

Cottage Lake Nubanusit

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Room  03 - Twin Room, vacation rental in Bennington
Room  03 - Twin Room, vacation rental in Bennington
Room  03 - Twin Room, vacation rental in Bennington

Room 03 - Twin Room

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Room 11- Double & Twin Room, vacation rental in Bennington
Room 11- Double & Twin Room, vacation rental in Bennington
Room 11- Double & Twin Room, vacation rental in Bennington

Room 11- Double & Twin Room

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Room 07 - Queen Room, vacation rental in Bennington
Room 07 - Queen Room, vacation rental in Bennington
Room 07 - Queen Room, vacation rental in Bennington

Room 07 - Queen Room

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Room 9 -  Queen Room, vacation rental in Bennington
Room 9 -  Queen Room, vacation rental in Bennington
Room 9 -  Queen Room, vacation rental in Bennington

Room 9 - Queen Room

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Room 12 - Double & Twin Room, vacation rental in Bennington
Room 12 - Double & Twin Room, vacation rental in Bennington
Room 12 - Double & Twin Room, vacation rental in Bennington

Room 12 - Double & Twin Room

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Room 08 - King Room  - Handicap accessible, vacation rental in Bennington
Room 08 - King Room  - Handicap accessible, vacation rental in Bennington
Room 08 - King Room  - Handicap accessible, vacation rental in Bennington

Room 08 - King Room - Handicap accessible

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Room 02 - Queen & Twin Room, vacation rental in Bennington
Room 02 - Queen & Twin Room, vacation rental in Bennington
Room 02 - Queen & Twin Room, vacation rental in Bennington

Room 02 - Queen & Twin Room

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Room 10 - Queen Room, vacation rental in Bennington
Room 10 - Queen Room, vacation rental in Bennington
Room 10 - Queen Room, vacation rental in Bennington

Room 10 - Queen Room

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Room 05  - King Room, vacation rental in Bennington
Room 05  - King Room, vacation rental in Bennington
Room 05  - King Room, vacation rental in Bennington

Room 05 - King Room

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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A spacious one bedroom apartment on a family farm in beautiful Monadnock Region., vacation rental in Bennington
A spacious one bedroom apartment on a family farm in beautiful Monadnock Region., vacation rental in Bennington
A spacious one bedroom apartment on a family farm in beautiful Monadnock Region., vacation rental in Bennington

A spacious one bedroom apartment on a family farm in beautiful Monadnock Region.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Luxe Riverfront Cottage w/ Dock by Lake Horace!, vacation rental in Bennington
Luxe Riverfront Cottage w/ Dock by Lake Horace!, vacation rental in Bennington
Luxe Riverfront Cottage w/ Dock by Lake Horace!, vacation rental in Bennington

Luxe Riverfront Cottage w/ Dock by Lake Horace!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Stunning & Scenic 2BR w/ Resort Pool Near Ski Area, vacation rental in Bennington
Stunning & Scenic 2BR w/ Resort Pool Near Ski Area, vacation rental in Bennington
Stunning & Scenic 2BR w/ Resort Pool Near Ski Area, vacation rental in Bennington

Stunning & Scenic 2BR w/ Resort Pool Near Ski Area

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Waterfront Cottage with Large Dock, vacation rental in Bennington
Waterfront Cottage with Large Dock, vacation rental in Bennington
Waterfront Cottage with Large Dock, vacation rental in Bennington

Waterfront Cottage with Large Dock

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Lakefront Cottage on Franklin Pierce Lake!, vacation rental in Bennington
Lakefront Cottage on Franklin Pierce Lake!, vacation rental in Bennington
Lakefront Cottage on Franklin Pierce Lake!, vacation rental in Bennington

Lakefront Cottage on Franklin Pierce Lake!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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The Rustic Retreat - Lakefront Cottage on Franklin Pierce Lake!, vacation rental in Bennington
The Rustic Retreat - Lakefront Cottage on Franklin Pierce Lake!, vacation rental in Bennington
The Rustic Retreat - Lakefront Cottage on Franklin Pierce Lake!, vacation rental in Bennington

The Rustic Retreat - Lakefront Cottage on Franklin Pierce Lake!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Private Hot Tub Suite, vacation rental in Bennington
Private Hot Tub Suite, vacation rental in Bennington
Private Hot Tub Suite, vacation rental in Bennington

Private Hot Tub Suite

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Hillsborough Village Retreat: Walk to River!, vacation rental in Bennington
Hillsborough Village Retreat: Walk to River!, vacation rental in Bennington
Hillsborough Village Retreat: Walk to River!, vacation rental in Bennington

Hillsborough Village Retreat: Walk to River!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Direct Waterfront, Year-Round, A-Frame Cabin, vacation rental in Bennington
Direct Waterfront, Year-Round, A-Frame Cabin, vacation rental in Bennington
Direct Waterfront, Year-Round, A-Frame Cabin, vacation rental in Bennington

Direct Waterfront, Year-Round, A-Frame Cabin

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Lakefront Cottage on Peaceful Horace Lake, vacation rental in Bennington
Lakefront Cottage on Peaceful Horace Lake, vacation rental in Bennington
Lakefront Cottage on Peaceful Horace Lake, vacation rental in Bennington

Lakefront Cottage on Peaceful Horace Lake

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Meadow House at Powder Mill Pond - a nature lover's paradise, vacation rental in Bennington
Meadow House at Powder Mill Pond - a nature lover's paradise, vacation rental in Bennington
Meadow House at Powder Mill Pond - a nature lover's paradise, vacation rental in Bennington

Meadow House at Powder Mill Pond - a nature lover's paradise

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Cottage on the Lake--You can't get any closer!, vacation rental in Bennington
Cottage on the Lake--You can't get any closer!, vacation rental in Bennington
Cottage on the Lake--You can't get any closer!, vacation rental in Bennington

Cottage on the Lake--You can't get any closer!

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Luxury Farm Stay-The Cottage at Glenrose - Wolf Pine Hollow, vacation rental in Bennington
Luxury Farm Stay-The Cottage at Glenrose - Wolf Pine Hollow, vacation rental in Bennington
Luxury Farm Stay-The Cottage at Glenrose - Wolf Pine Hollow, vacation rental in Bennington

Luxury Farm Stay-The Cottage at Glenrose - Wolf Pine Hollow

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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2 lakefront cottages on Franklin Pierce Lake, vacation rental in Bennington
2 lakefront cottages on Franklin Pierce Lake, vacation rental in Bennington
2 lakefront cottages on Franklin Pierce Lake, vacation rental in Bennington

2 lakefront cottages on Franklin Pierce Lake

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Private Lakehouse Getaway for relaxing and fun!, vacation rental in Bennington
Private Lakehouse Getaway for relaxing and fun!, vacation rental in Bennington
Private Lakehouse Getaway for relaxing and fun!, vacation rental in Bennington

Private Lakehouse Getaway for relaxing and fun!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Modern Francestown Retreat on Scobie Pond!, vacation rental in Bennington
Modern Francestown Retreat on Scobie Pond!, vacation rental in Bennington
Modern Francestown Retreat on Scobie Pond!, vacation rental in Bennington

Modern Francestown Retreat on Scobie Pond!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Spectacular Log Home with Private Lake Access, vacation rental in Bennington
Spectacular Log Home with Private Lake Access, vacation rental in Bennington
Spectacular Log Home with Private Lake Access, vacation rental in Bennington

Spectacular Log Home with Private Lake Access

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Stone Pond Farm sleeps 9, peaceful, family friendly, quaint country farmhouse., vacation rental in Bennington
Stone Pond Farm sleeps 9, peaceful, family friendly, quaint country farmhouse., vacation rental in Bennington
Stone Pond Farm sleeps 9, peaceful, family friendly, quaint country farmhouse., vacation rental in Bennington

Stone Pond Farm sleeps 9, peaceful, family friendly, quaint country farmhouse.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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Lakeside Francestown Home w/ Private Dock & Porch!, vacation rental in Bennington
Lakeside Francestown Home w/ Private Dock & Porch!, vacation rental in Bennington
Lakeside Francestown Home w/ Private Dock & Porch!, vacation rental in Bennington

Lakeside Francestown Home w/ Private Dock & Porch!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Authentic Red Farm House On Zephyr Lake, Beautiful In All Seasons!, vacation rental in Bennington
Authentic Red Farm House On Zephyr Lake, Beautiful In All Seasons!, vacation rental in Bennington
Authentic Red Farm House On Zephyr Lake, Beautiful In All Seasons!, vacation rental in Bennington

Authentic Red Farm House On Zephyr Lake, Beautiful In All Seasons!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Secluded Lake House, Private Beach For Swimming or Boating, Kids & Pets Welcome, vacation rental in Bennington
Secluded Lake House, Private Beach For Swimming or Boating, Kids & Pets Welcome, vacation rental in Bennington
Secluded Lake House, Private Beach For Swimming or Boating, Kids & Pets Welcome, vacation rental in Bennington

Secluded Lake House, Private Beach For Swimming or Boating, Kids & Pets Welcome

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Luxury Farm Stay - Bonds Corner Bungalow - Wolf Pine Hollow, vacation rental in Bennington
Luxury Farm Stay - Bonds Corner Bungalow - Wolf Pine Hollow, vacation rental in Bennington
Luxury Farm Stay - Bonds Corner Bungalow - Wolf Pine Hollow, vacation rental in Bennington

Luxury Farm Stay - Bonds Corner Bungalow - Wolf Pine Hollow

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Grey Heron Lake House- Super Cozy Family Guest Home Right on the Water!, vacation rental in Bennington
Grey Heron Lake House- Super Cozy Family Guest Home Right on the Water!, vacation rental in Bennington
Grey Heron Lake House- Super Cozy Family Guest Home Right on the Water!, vacation rental in Bennington

Grey Heron Lake House- Super Cozy Family Guest Home Right on the Water!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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5 Bedroom cozy New England home - Cobb Meadow House, vacation rental in Bennington
5 Bedroom cozy New England home - Cobb Meadow House, vacation rental in Bennington
5 Bedroom cozy New England home - Cobb Meadow House, vacation rental in Bennington

5 Bedroom cozy New England home - Cobb Meadow House

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Luxury Farm Stay at The Lodge at Wolf Pine Hollow, vacation rental in Bennington
Luxury Farm Stay at The Lodge at Wolf Pine Hollow, vacation rental in Bennington
Luxury Farm Stay at The Lodge at Wolf Pine Hollow, vacation rental in Bennington

Luxury Farm Stay at The Lodge at Wolf Pine Hollow

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Lakefront Luxury Home on Horace Lake, vacation rental in Bennington
Lakefront Luxury Home on Horace Lake, vacation rental in Bennington
Lakefront Luxury Home on Horace Lake, vacation rental in Bennington

Lakefront Luxury Home on Horace Lake

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
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Luxury Farm Stay at Glenrose Manor - Wolf Pine Hollow, vacation rental in Bennington
Luxury Farm Stay at Glenrose Manor - Wolf Pine Hollow, vacation rental in Bennington
Luxury Farm Stay at Glenrose Manor - Wolf Pine Hollow, vacation rental in Bennington

Luxury Farm Stay at Glenrose Manor - Wolf Pine Hollow

Rental Home
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
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Showing results 1-49 of 49
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