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North Bennington Holiday Rentals

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50 rentals in North Bennington.
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Romantic Bennington Vermont Cottage, holiday rental in North Bennington

Romantic Bennington Vermont Cottage

1 bedroom
1 bathroom
Sleeps 4
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Cozy 1 Bedroom farm stay cottage, holiday rental in North Bennington

Cozy 1 Bedroom farm stay cottage

1 bedroom
1 bathroom
Sleeps 4
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Romantic Waterfront Vermont Cottage, holiday rental in North Bennington

Romantic Waterfront Vermont Cottage

1 bedroom
1 bathroom
Sleeps 4
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Renovated 2 Bedroom Cottage With View Of The Roaring Branch From 2nd Floor, holiday rental in North Bennington

Renovated 2 Bedroom Cottage With View Of The Roaring Branch From 2nd Floor

2 bedrooms
1 bathroom
Sleeps 6
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Huge Luxe Williamstown Updated Victorian,  All Ensuite Baths, Walk to Spring St!, holiday rental in North Bennington

Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!

5 bedrooms
6 bathrooms
Sleeps 15
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Charming Downtown Williamstown Cottage - 5 Min Walk to Campus, holiday rental in North Bennington

Charming Downtown Williamstown Cottage - 5 Min Walk to Campus

3 bedrooms
2 bathrooms
Sleeps 7
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Great Place to get away and have clean fresh air surround you!, holiday rental in North Bennington

Great Place to get away and have clean fresh air surround you!

1 bedroom
1 bathroom
Sleeps 6
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Spacious Mountain view home Booking Fall/Winter 2020-21, holiday rental in North Bennington

Spacious Mountain view home Booking Fall/Winter 2020-21

5 bedrooms
3 bathrooms
Sleeps 12
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Victorian Home in Bennington, Vermont, holiday rental in North Bennington

Victorian Home in Bennington, Vermont

3 bedrooms
3 bathrooms
Sleeps 7
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1828 Vermont Cottage Feet From The Famous Battenkill River, holiday rental in North Bennington

1828 Vermont Cottage Feet From The Famous Battenkill River

3 bedrooms
2 bathrooms
Sleeps 5
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All season lake front getaway!, holiday rental in North Bennington

All season lake front getaway!

1 bedroom
1 bathroom
Sleeps 4
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Historic 1913 Railroad Station Full of History, Views and Modern Amentities!, holiday rental in North Bennington

Historic 1913 Railroad Station Full of History, Views and Modern Amentities!

3 bedrooms
2 bathrooms
Sleeps 6
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200 Yr old Farmhouse on 45 acres, holiday rental in North Bennington

200 Yr old Farmhouse on 45 acres

2 bedrooms
2 bathrooms
Sleeps 6
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Perfect for a peaceful get away in clean fresh Vermont air!, holiday rental in North Bennington

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

3 bedrooms
5 bathrooms
Sleeps 6
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LITTLE BIT OF HEAVEN in Southern VT - Mt Snow, Berkshires, Bennington, Mass Moca, holiday rental in North Bennington

LITTLE BIT OF HEAVEN in Southern VT - Mt Snow, Berkshires, Bennington, Mass Moca

3 bedrooms
1 bathroom
Sleeps 6
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A roomy remodeled retreat close to MassMoCA, holiday rental in North Bennington

A roomy remodeled retreat close to MassMoCA

4 bedrooms
2 bathrooms
Sleeps 8
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Escape the Chaos! Private cabin/ 40 Acres, holiday rental in North Bennington

Escape the Chaos! Private cabin/ 40 Acres

3 bedrooms
1 bathroom
Sleeps 7
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Country Getaway Lodge / Ranch, holiday rental in North Bennington

Country Getaway Lodge / Ranch

5 bedrooms
4 bathrooms
Sleeps 14
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Kayaker & Fly-fisher DREAM, private BattenKill waterfront super charming home, holiday rental in North Bennington

Kayaker & Fly-fisher DREAM, private BattenKill waterfront super charming home

3 bedrooms
2 bathrooms
Sleeps 4
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1920's Bennington Vermont Guest Barn, holiday rental in North Bennington

1920's Bennington Vermont Guest Barn

3 bedrooms
1 bathroom
Sleeps 7
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Vermont Hillside Retreat, holiday rental in North Bennington

Vermont Hillside Retreat

4 bedrooms
2 bathrooms
Sleeps 12
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New home in the heart of the Green Mountain Forest, holiday rental in North Bennington

New home in the heart of the Green Mountain Forest

3 bedrooms
2 bathrooms
Sleeps 6
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Bennington Guest Farmhouse, holiday rental in North Bennington

Bennington Guest Farmhouse

5 bedrooms
2 bathrooms
Sleeps 9
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Mountain- Top Cabin With Direct Vast Access In Green Mountain National Forest, holiday rental in North Bennington

Mountain- Top Cabin With Direct Vast Access In Green Mountain National Forest

2 bedrooms
1 bathroom
Sleeps 6
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Cozy and quaint country cottage, walk to downtown Williamstown, holiday rental in North Bennington

Cozy and quaint country cottage, walk to downtown Williamstown

2 bedrooms
1 bathroom
Sleeps 4
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NEW LISTING - Cozy Mountain Retreat on the Roaring Branch - dogs welcome, holiday rental in North Bennington

NEW LISTING - Cozy Mountain Retreat on the Roaring Branch - dogs welcome

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Tutti Farm - 6 Bed 3 Bath 1847 Farmhouse Upstate NY, holiday rental in North Bennington

Tutti Farm - 6 Bed 3 Bath 1847 Farmhouse Upstate NY

6 bedrooms
3 bathrooms
Sleeps 12
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Awesome Mountain Views at this Studio with Loft, holiday rental in North Bennington

Awesome Mountain Views at this Studio with Loft

2 bedrooms
2 bathrooms
Sleeps 5
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Historic c.1880 Victorian MA/VT border near Williams College MassMoCA Freshgrass, holiday rental in North Bennington

Historic c.1880 Victorian MA/VT border near Williams College MassMoCA Freshgrass

5 bedrooms
2 bathrooms
Sleeps 12
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Stunning Post and Beam Art Studio/House, holiday rental in North Bennington

Stunning Post and Beam Art Studio/House

3 bedrooms
1 bathroom
Sleeps 6
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The Gathering at High Mowing Williamstown, holiday rental in North Bennington

The Gathering at High Mowing Williamstown

4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Country living at its finest!, holiday rental in North Bennington

Country living at its finest!

1 bedroom
1 bathroom
Sleeps 4
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Cozy cabin w/ wood firepace, shared seasonal pool & tranquil views - dogs OK!, holiday rental in North Bennington

Cozy cabin w/ wood firepace, shared seasonal pool & tranquil views - dogs OK!

4 bedrooms
3 bathrooms
Sleeps 8
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Green Mountain Retreat, holiday rental in North Bennington

Green Mountain Retreat

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning Views of the Equinox, holiday rental in North Bennington

Stunning Views of the Equinox

5 bedrooms
3 bathrooms
Sleeps 12
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Karin's Place, holiday rental in North Bennington

Karin's Place

7 bedrooms
6 bathrooms
Sleeps 30
Match: Sleeps
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Country Farmhouse with Views, holiday rental in North Bennington

Country Farmhouse with Views

4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Artists' Dream Space in the Center of Downtown Be, holiday rental in North Bennington

Artists' Dream Space in the Center of Downtown Be

0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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The Lodge at Fox Hollow, holiday rental in North Bennington

The Lodge at Fox Hollow

2 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Tentrr Signature Site - Fortunate Ewe Farm, holiday rental in North Bennington

Tentrr Signature Site - Fortunate Ewe Farm

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Runamuk Farm, holiday rental in North Bennington

Tentrr Signature Site - Runamuk Farm

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Historic Arlington 'Deming House' on Route 7A, holiday rental in North Bennington

Historic Arlington 'Deming House' on Route 7A

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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1 Bed, 1st floor, furnished, includes utilities, TV+internet, holiday rental in North Bennington

1 Bed, 1st floor, furnished, includes utilities, TV+internet

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Wilmington Retreat w/ Deck, Lake Views & Game Room, holiday rental in North Bennington

Wilmington Retreat w/ Deck, Lake Views & Game Room

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Meme's High Mountain Lake House, holiday rental in North Bennington

Meme's High Mountain Lake House

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Luxe 'Green Barn' Near Skiing w/ Mt Equinox Views!, holiday rental in North Bennington

Luxe 'Green Barn' Near Skiing w/ Mt Equinox Views!

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Two Brooks Lodge, holiday rental in North Bennington

Two Brooks Lodge

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Unique Vermont Log Cabin Nestled in Red Mountains

0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
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NEW! 13-Acre Manchester Retreat, 13 Mi to Bromley!, holiday rental in North Bennington

NEW! 13-Acre Manchester Retreat, 13 Mi to Bromley!

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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NEW! Peaceful Family Home w/ Fire Pit & Large Yard, holiday rental in North Bennington

NEW! Peaceful Family Home w/ Fire Pit & Large Yard

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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