Bennington Holiday Apartments
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50 rentals in Bennington.
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Romantic Bennington Vermont Cottage
1 bedroom
1 bathroom
Sleeps 4
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Victorian Home in Bennington, Vermont
3 bedrooms
3 bathrooms
Sleeps 7
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1920's Bennington Vermont Guest Barn
3 bedrooms
1 bathroom
Sleeps 7
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Bennington Guest Farmhouse
5 bedrooms
2 bathrooms
Sleeps 9
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Cozy 1 Bedroom farm stay cottage
1 bedroom
1 bathroom
Sleeps 4
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Romantic Waterfront Vermont Cottage
1 bedroom
1 bathroom
Sleeps 4
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Two Brooks Lodge
3 bedrooms
1 bathroom
Sleeps 6
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Karin's Place
7 bedrooms
6 bathrooms
Sleeps 30
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Artists' Dream Space in the Center of Downtown Be
0 bedrooms
1 bathroom
Sleeps 3
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Renovated 2 Bedroom Cottage With View Of The Roaring Branch From 2nd Floor
2 bedrooms
1 bathroom
Sleeps 6
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Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow
4 bedrooms
3 bathrooms
Sleeps 12
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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
3 bedrooms
2 bathrooms
Sleeps 7
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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
5 bedrooms
3 bathrooms
Sleeps 12
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1828 Vermont Cottage Feet From The Famous Battenkill River
3 bedrooms
2 bathrooms
Sleeps 5
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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
2 bedrooms
2 bathrooms
Sleeps 6
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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
3 bedrooms
1 bathroom
Sleeps 6
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A roomy remodeled retreat close to MassMoCA
4 bedrooms
2 bathrooms
Sleeps 8
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Escape the Chaos! Private cabin/ 40 Acres
3 bedrooms
1 bathroom
Sleeps 7
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4 BR, 2BA: Comfy, Clean & Family Friendly - 15 mins to Mount Snow!
4 bedrooms
2 bathrooms
Sleeps 8
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Beautiful Vermont Vacation Home- Mount Snow!!
4 bedrooms
2 bathrooms
Sleeps 14
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Kayaker & Fly-fisher DREAM, private BattenKill waterfront super charming home
3 bedrooms
2 bathrooms
Sleeps 4
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Vermont Hillside Retreat
4 bedrooms
2 bathrooms
Sleeps 12
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New home in the heart of the Green Mountain Forest
3 bedrooms
2 bathrooms
Sleeps 6
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Mountain- Top Cabin With Direct Vast Access In Green Mountain National Forest
2 bedrooms
1 bathroom
Sleeps 6
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Cozy Mountain Escape to Southern Vermont
3 bedrooms
2 bathrooms
Sleeps 8
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Cozy and quaint country cottage, walk to downtown Williamstown
2 bedrooms
1 bathroom
Sleeps 4
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Cozy Vermont home for your Summer and Fall getaway
4 bedrooms
2 bathrooms
Sleeps 9
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NEW LISTING - Cozy Mountain Retreat on the Roaring Branch - dogs welcome
2 bedrooms
1 bathroom
Sleeps 4
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Tutti Farm - 6 Bed 3 Bath 1847 Farmhouse Upstate NY
6 bedrooms
3 bathrooms
Sleeps 12
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Cozy 4 season getaway in Vermont near Mt. Snow
3 bedrooms
2 bathrooms
Sleeps 13
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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
3 bedrooms
1 bathroom
Sleeps 6
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Designer Vermont Vacation Retreat
4 bedrooms
2 bathrooms
Sleeps 10
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The Gathering at High Mowing Williamstown
4 bedrooms
3 bathrooms
Sleeps 7
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Green Mountain Retreat
3 bedrooms
2 bathrooms
Sleeps 6
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Country Farmhouse with Views
4 bedrooms
4 bathrooms
Sleeps 6
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Mountain Retreat - Chimney Hill - 7 Miles to Mount Snow - direct VAST access
3 bedrooms
2 bathrooms
Sleeps 6
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The Lodge at Fox Hollow
2 bedrooms
3 bathrooms
Sleeps 7
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The Bear Den
1 bedroom
1 bathroom
Sleeps 2
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Tentrr Signature Site - Fortunate Ewe Farm
1 bedroom
1 bathroom
Sleeps 4
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Tentrr Signature Site - Hidden Hoosic Riverside Camp
1 bedroom
1 bathroom
Sleeps 4
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Historic Arlington 'Deming House' on Route 7A
3 bedrooms
4 bathrooms
Sleeps 6
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Wilmington Retreat w/ Deck, Lake Views & Game Room
5 bedrooms
4 bathrooms
Sleeps 14
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Meme's High Mountain Lake House
3 bedrooms
2 bathrooms
Sleeps 7
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Unique Vermont Log Cabin Nestled in Red Mountains
0 bedrooms
0 bathrooms
Sleeps 0
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NEW! Peaceful Family Home w/ Fire Pit & Large Yard
4 bedrooms
3 bathrooms
Sleeps 6
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Frequently Asked Questions about Bennington
- Yes, here are some popular holiday rentals in Bennington that have a pool:See all holiday rentals with a pool in Bennington on Tripadvisor
- Yes, here are some popular holiday rentals in Bennington that have internet access:See all holiday rentals in Bennington on Tripadvisor
- The best pet friendly rentals in Bennington are:See all pet friendly holiday rentals in Bennington on Tripadvisor
- Some of the most popular kid friendly rentals in Bennington are:See all kid friendly holiday rentals in Bennington on Tripadvisor