We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Homes in Bennington

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Distance from
1 km
Price per night
$0
$1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighbourhood
50 rentals in Bennington.
Sort by:
Tripadvisor Sort
Romantic Bennington Vermont Cottage, holiday rental in Bennington

Romantic Bennington Vermont Cottage

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Victorian Home in Bennington, Vermont, holiday rental in Bennington

Victorian Home in Bennington, Vermont

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
1920's Bennington Vermont Guest Barn, holiday rental in Bennington

1920's Bennington Vermont Guest Barn

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Bennington Guest Farmhouse, holiday rental in Bennington

Bennington Guest Farmhouse

5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Romantic Waterfront Vermont Cottage, holiday rental in Bennington

Romantic Waterfront Vermont Cottage

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Two Brooks Lodge, holiday rental in Bennington

Two Brooks Lodge

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Karin's Place, holiday rental in Bennington

Karin's Place

7 bedrooms
6 bathrooms
Sleeps 30
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Artists' Dream Space in the Center of Downtown Be, holiday rental in Bennington

Artists' Dream Space in the Center of Downtown Be

0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Cozy 1 Bedroom farm stay cottage, holiday rental in Bennington

Cozy 1 Bedroom farm stay cottage

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Renovated 2 Bedroom Cottage With View Of The Roaring Branch From 2nd Floor, holiday rental in Bennington

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Save time - get the best Bennington rentals sent straight to your email!
Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow, holiday rental in Bennington

Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Huge Luxe Williamstown Updated Victorian,  All Ensuite Baths, Walk to Spring St!, holiday rental in Bennington

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

5 bedrooms
6 bathrooms
Sleeps 15
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Great Place to get away and have clean fresh air surround you!, holiday rental in Bennington

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

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Charming Downtown Williamstown Cottage - 5 Min Walk to Campus, holiday rental in Bennington

Charming Downtown Williamstown Cottage - 5 Min Walk to Campus

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Spacious Mountain view home Booking Fall/Winter 2020-21, holiday rental in Bennington

Spacious Mountain view home Booking Fall/Winter 2020-21

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
1828 Vermont Cottage Feet From The Famous Battenkill River, holiday rental in Bennington

1828 Vermont Cottage Feet From The Famous Battenkill River

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Historic 1913 Railroad Station Full of History, Views and Modern Amentities!, holiday rental in Bennington

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

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
200 Yr old Farmhouse on 45 acres, holiday rental in Bennington

200 Yr old Farmhouse on 45 acres

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Perfect for a peaceful get away in clean fresh Vermont air!, holiday rental in Bennington

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

3 bedrooms
5 bathrooms
Sleeps 6
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
LITTLE BIT OF HEAVEN in Southern VT - Mt Snow, Berkshires, Bennington, Mass Moca, holiday rental in Bennington

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

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
4 BR, 2BA: Comfy, Clean & Family Friendly - 15 mins to Mount Snow!, holiday rental in Bennington

4 BR, 2BA: Comfy, Clean & Family Friendly - 15 mins to Mount Snow!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Beautiful  Vermont Vacation Home- Mount Snow!!, holiday rental in Bennington

Beautiful Vermont Vacation Home- Mount Snow!!

4 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
A roomy remodeled retreat close to MassMoCA, holiday rental in Bennington

A roomy remodeled retreat close to MassMoCA

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Escape the Chaos! Private cabin/ 40 Acres, holiday rental in Bennington

Escape the Chaos! Private cabin/ 40 Acres

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Kayaker & Fly-fisher DREAM, private BattenKill waterfront super charming home, holiday rental in Bennington

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

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Vermont Hillside Retreat, holiday rental in Bennington

Vermont Hillside Retreat

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
New home in the heart of the Green Mountain Forest, holiday rental in Bennington

New home in the heart of the Green Mountain Forest

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Mountain- Top Cabin With Direct Vast Access In Green Mountain National Forest, holiday rental in Bennington

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Shaftsbury Vermont Farm House Full Of History, Views, And Classic Beauty, holiday rental in Bennington

Shaftsbury Vermont Farm House Full Of History, Views, And Classic Beauty

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Cozy Mountain Escape to Southern Vermont, holiday rental in Bennington

Cozy Mountain Escape to Southern Vermont

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Cozy and quaint country cottage, walk to downtown Williamstown, holiday rental in Bennington

Cozy and quaint country cottage, walk to downtown Williamstown

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Cozy Vermont home for your Summer and Fall getaway, holiday rental in Bennington

Cozy Vermont home for your Summer and Fall getaway

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
NEW LISTING - Cozy Mountain Retreat on the Roaring Branch - dogs welcome, holiday rental in Bennington

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

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Tutti Farm - 6 Bed 3 Bath 1847 Farmhouse Upstate NY, holiday rental in Bennington

Tutti Farm - 6 Bed 3 Bath 1847 Farmhouse Upstate NY

6 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Cozy 4 season getaway in Vermont near Mt. Snow, holiday rental in Bennington

Cozy 4 season getaway in Vermont near Mt. Snow

3 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Historic c.1880 Victorian MA/VT border near Williams College MassMoCA Freshgrass, holiday rental in Bennington

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

5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Stunning Post and Beam Art Studio/House, holiday rental in Bennington

Stunning Post and Beam Art Studio/House

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Designer Vermont Vacation Retreat, holiday rental in Bennington

Designer Vermont Vacation Retreat

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
The Gathering at High Mowing Williamstown, holiday rental in Bennington

The Gathering at High Mowing Williamstown

4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Green Mountain Retreat, holiday rental in Bennington

Green Mountain Retreat

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Country Farmhouse with Views, holiday rental in Bennington

Country Farmhouse with Views

4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Mountain Retreat - Chimney Hill - 7 Miles to Mount Snow - direct VAST access, holiday rental in Bennington

Mountain Retreat - Chimney Hill - 7 Miles to Mount Snow - direct VAST access

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
The Lodge at Fox Hollow, holiday rental in Bennington

The Lodge at Fox Hollow

2 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
The Bear Den, holiday rental in Bennington

The Bear Den

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Tentrr Signature Site - Fortunate Ewe Farm, holiday rental in Bennington

Tentrr Signature Site - Fortunate Ewe Farm

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Tentrr Signature Site - Hidden Hoosic   Riverside Camp, holiday rental in Bennington

Tentrr Signature Site - Hidden Hoosic Riverside Camp

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Historic Arlington 'Deming House' on Route 7A, holiday rental in Bennington

Historic Arlington 'Deming House' on Route 7A

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Wilmington Retreat w/ Deck, Lake Views & Game Room, holiday rental in Bennington

Wilmington Retreat w/ Deck, Lake Views & Game Room

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Meme's High Mountain Lake House, holiday rental in Bennington

Meme's High Mountain Lake House

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out

Unique Vermont Log Cabin Nestled in Red Mountains

0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
PreviousNext
1
Frequently Asked Questions about Bennington