Bennington Area Vacation Rentals - Bennington Area, Vermont Vacation Rental Deals on Lake Rentals, Beach Houses, Condos, Cabins, Villas by VacaGuru.com!

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

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Shaftsbury Vermont Private vacation home From $200 per night (USD)

Seven Springs House Nestled in the Heart of Dorset

Seven Springs House Nestled in the Heart of Dorset

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12

Dorset Vermont Private vacation home Click For Pricing

$Manchester Center Home w\/ Green Mtn Views!$

Manchester Center Home w\/ Green Mtn Views!

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Manchester Center Vermont Private vacation home From $201 per night (USD)

Getaway to the green mountain

Getaway to the green mountain

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10

Manchester Vermont Private vacation home From $354 per night (USD)

$3 Mountain View home minutes to Stratton\/Bromley$

3 Mountain View home minutes to Stratton\/Bromley

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winhall Vermont Private vacation home From $540 per night (USD)

$*Shred Shack* Hot Tub w\/ Majestic Valley Views$

*Shred Shack* Hot Tub w\/ Majestic Valley Views

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12

Winhall Vermont Private vacation home From $370 per night (USD)

Owners Own Unit on Bromley Mountain - gorgeous views yet close to Manchester

Owners Own Unit on Bromley Mountain - gorgeous views yet close to Manchester

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Peru Vermont Condo Click For Pricing

Stratton home with spectacular mountain view and hot tub!

Stratton home with spectacular mountain view and hot tub!

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12

Winhall Vermont Private vacation home From $560 per night (USD)

Cozy ski home with amazing views of Stratton & Bromley Mountains.

Cozy ski home with amazing views of Stratton & Bromley Mountains.

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Winhall Vermont Private vacation home From $600 per night (USD)

This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.

This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.

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Manchester Vermont Cottage From $240 per night (USD)

$Hike In\/Hike Out VTFun$

Hike In\/Hike Out VTFun

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Peru Vermont Condo From $248 per night (USD)

Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!

Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!

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Dorset Vermont Cottage From $349 per night (USD)

Lake life at Woodford Cottage

Lake life at Woodford Cottage

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Bennington Vermont Cottage From $199 per night (USD)

$Luxury Oasis w\/Serene Views! Close to Ski Slopes w\/Shuttle. Gameroom. Golf. WiFi$

Luxury Oasis w\/Serene Views! Close to Ski Slopes w\/Shuttle. Gameroom. Golf. WiFi

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Winhall Vermont Private vacation home From $543 per night (USD)

The Bear Ski House - 5 mins from Stratton Mountain

The Bear Ski House - 5 mins from Stratton Mountain

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16

Winhall Vermont Private vacation home From $760 per night (USD)

School Street House in heart of Manchester Center

School Street House in heart of Manchester Center

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Manchester Vermont Private vacation home From $723 per night (USD)

Centrally located condo…minutes from major ski resorts.

Centrally located condo…minutes from major ski resorts.

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Manchester center Vermont Condo From $209 per night (USD)

$Dog-Friendly Two-Story House w\/Free WiFi, Wood Fireplace, Gas Grill, Jetted Tub$

Dog-Friendly Two-Story House w\/Free WiFi, Wood Fireplace, Gas Grill, Jetted Tub

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Stratton Vermont Private vacation home From $345 per night (USD)

MLK WEEKEND DISCOUNT! Fireside Fun. Ski vacations & Family Reunion dream house: Huge covered deck, double height ceilings, great hang out space. Dogs welcome.

MLK WEEKEND DISCOUNT! Fireside Fun. Ski vacations & Family Reunion dream house: Huge covered deck, double height ceilings, great hang out space. Dogs welcome.

6
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12

Manchester Vermont Private vacation home From $785 per night (USD)

Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.

Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.

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Winhall Vermont Chalet From $340 per night (USD)

Adventure Home: Trails, Pool, Gym & Tennis Access

Adventure Home: Trails, Pool, Gym & Tennis Access

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8

Peru Vermont Condo From $704 per night (USD)

13-Acre Manchester Retreat: 13 Miles to Bromley!

13-Acre Manchester Retreat: 13 Miles to Bromley!

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Manchester Vermont Private vacation home From $487 per night (USD)

Spacious + Private Ski Lodge on 20+ Acres - 10 min to Stratton, 5 min to Bromley

Spacious + Private Ski Lodge on 20+ Acres - 10 min to Stratton, 5 min to Bromley

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Winhall Vermont Private vacation home From $681 per night (USD)

Enchanted Mountain House

Enchanted Mountain House

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East Dorset Vermont Private vacation home Click For Pricing

Comfortable condo with pool & clubhouse fitness room, forest views

Comfortable condo with pool & clubhouse fitness room, forest views

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Peru Vermont Condo From $83 per night (USD)

Snow Has Arrived Dorset Hone by Skiing

Snow Has Arrived Dorset Hone by Skiing

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Dorset Vermont Private vacation home Click For Pricing

Unique Vermont Log Cabin Nestled in Red Mountains

Unique Vermont Log Cabin Nestled in Red Mountains

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Arlington Vermont Private vacation home From $900 per night (USD)

Victorian Home in Bennington, Vermont

Victorian Home in Bennington, Vermont

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Bennington Vermont Private vacation home From $288 per night (USD)

This house is a 2 bedroom(s), 2.5 bathrooms, located in Manchester, VT.

This house is a 2 bedroom(s), 2.5 bathrooms, located in Manchester, VT.

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Manchester Vermont Private vacation home From $292 per night (USD)

$Gorgeous Victorian-Style House w\/ Hilltop Pool!$

Gorgeous Victorian-Style House w\/ Hilltop Pool!

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Rupert Vermont Villa From $540 per night (USD)

$Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer\/Dryer, & Pond$

Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer\/Dryer, & Pond

3
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12

Winhall Vermont Private vacation home From $226 per night (USD)

Quiet, spacious, private, beautiful views above art studio

Quiet, spacious, private, beautiful views above art studio

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Shaftsbury Vermont Apartment From $140 per night (USD)

Private home on 37 acres with stunning mountain views

Private home on 37 acres with stunning mountain views

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Shaftsbury Vermont Private vacation home From $467 per night (USD)

$Manchester Center Retreat w\/ Mtn View, Near Skiing$

Manchester Center Retreat w\/ Mtn View, Near Skiing

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Manchester Center Vermont Apartment From $143 per night (USD)

$Incredible 4BR \/ 4BA Home Sets the Stratton Views & Luxury Bar!$

Incredible 4BR \/ 4BA Home Sets the Stratton Views & Luxury Bar!

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Winhall Vermont Private vacation home From $1048 per night (USD)

Luxury 9 BRs Stratton Estate. Total Privacy & Incredible Views! Swimming Pool

Luxury 9 BRs Stratton Estate. Total Privacy & Incredible Views! Swimming Pool

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Winhall Vermont Private vacation home From $2649 per night (USD)

Unexpected Style in a Cosy, Convenient In-Town Apartment

Unexpected Style in a Cosy, Convenient In-Town Apartment

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Manchester Center Vermont Apartment From $195 per night (USD)

Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

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8

Sunderland Vermont Private vacation home Click For Pricing

Cozy 1 Bedroom farm stay cottage

Cozy 1 Bedroom farm stay cottage

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North bennington Vermont Private vacation home From $113 per night (USD)

This house is a 4 bedroom(s), 2.5 bathrooms, located in Manchester, VT.

This house is a 4 bedroom(s), 2.5 bathrooms, located in Manchester, VT.

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Manchester Vermont Private vacation home From $392 per night (USD)

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

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

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Manchester Center Vermont Apartment From $217 per night (USD)

Miner Cottage-Historic Antique Home just steps from the Equinox Resort

Miner Cottage-Historic Antique Home just steps from the Equinox Resort

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Manchester Vermont Private vacation home From $950 per night (USD)

Seven Springs Barn Nestled in the Heart of Dorset

Seven Springs Barn Nestled in the Heart of Dorset

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Dorset Vermont Chalet Click For Pricing

Palmer House Resort - Deluxe Two Double Beds 1

Palmer House Resort - Deluxe Two Double Beds 1

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Manchester Center, Vermont Hotel resort From $179 per night (USD)

Palmer House Resort - Deluxe King Bed 5

Palmer House Resort - Deluxe King Bed 5

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Manchester Center, , VT, US Vermont Hotel resort From $159 per night (USD)

Palmer House Resort - Deluxe Two Double Beds 2

Palmer House Resort - Deluxe Two Double Beds 2

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Manchester Center, Vermont Hotel resort From $179 per night (USD)

Palmer House Resort - Deluxe Two Double Beds 3

Palmer House Resort - Deluxe Two Double Beds 3

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Manchester Center, Vermont Hotel resort From $179 per night (USD)

Palmer House Resort - Deluxe Two Double Beds 5

Palmer House Resort - Deluxe Two Double Beds 5

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Manchester Center Vermont Hotel resort From $179 per night (USD)

Palmer House Resort - Deluxe Two Double Beds 4

Palmer House Resort - Deluxe Two Double Beds 4

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Manchester Center, Vermont Hotel resort From $179 per night (USD)

Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT

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Arlington Vermont Apartment From $190 per night (USD)

Palmer House Resort - Deluxe King Bed 2

Palmer House Resort - Deluxe King Bed 2

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Manchester Center, Vermont Hotel resort From $159 per night (USD)

Palmer House Resort - Deluxe King Bed 1

Palmer House Resort - Deluxe King Bed 1

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Manchester Center, Vermont Hotel resort From $159 per night (USD)

Palmer House Resort - Deluxe King Bed 3

Palmer House Resort - Deluxe King Bed 3

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Manchester Center, Vermont Hotel resort From $159 per night (USD)

Palmer House Resort - Deluxe King Bed 4

Palmer House Resort - Deluxe King Bed 4

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Manchester Center, Vermont Hotel resort From $159 per night (USD)

$Whimsical Winhall Cottage w\/ Fire Pit!$

Whimsical Winhall Cottage w\/ Fire Pit!

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Winhall Vermont Private vacation home Click For Pricing

Bright & cheery condo with seasonal pool access

Bright & cheery condo with seasonal pool access

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Peru Vermont Condo From $124 per night (USD)

Charming chalet near skiing & town with WiFi & wood-burning fireplace

Charming chalet near skiing & town with WiFi & wood-burning fireplace

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Winhall Vermont Chalet Click For Pricing

Huge Vermont Village Getaway

Huge Vermont Village Getaway

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Dorset Vermont Private vacation home From $392 per night (USD)

Renovated 2BR King Suite 2BA @ Mt Base Walk 2 All

Renovated 2BR King Suite 2BA @ Mt Base Walk 2 All

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Stratton Mountain Vermont Condo From $540 per night (USD)

*Hilltop Hideaway* Hot Tub in Iconic Chalet

*Hilltop Hideaway* Hot Tub in Iconic Chalet

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Winhall Vermont Private vacation home From $412 per night (USD)

$Ski-In\/Ski-Out Peru Condo at Bromley Mountain$

Ski-In\/Ski-Out Peru Condo at Bromley Mountain

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Peru Vermont Condo From $262 per night (USD)

Luxury Condo @ Mt Base 3BR 2BA Heated Pool Hot Tub

Luxury Condo @ Mt Base 3BR 2BA Heated Pool Hot Tub

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Winhall Vermont Condo From $637 per night (USD)

East Dorset Sanctuary

East Dorset Sanctuary

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East Dorset Vermont Private vacation home From $800 per night (USD)

Spacious A-Frame chalet, minutes to Stratton Mountain, Winhall, VT

Spacious A-Frame chalet, minutes to Stratton Mountain, Winhall, VT

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Winhall Vermont Private vacation home From $300 per night (USD)

$Magnificent Vermont home w\/free WiFi, full kitchen, firepit, patio, & deck$

Magnificent Vermont home w\/free WiFi, full kitchen, firepit, patio, & deck

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Sunderland Vermont Private vacation home Click For Pricing

Beautiful Southern Vermont Farmhouse on 100 Acres, Spectacular Views, Swim Pond

Beautiful Southern Vermont Farmhouse on 100 Acres, Spectacular Views, Swim Pond

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Stamford Vermont Private vacation home Click For Pricing

Beautiful ski house located between Stratton, Bromley and Magic

Beautiful ski house located between Stratton, Bromley and Magic

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Winhall Vermont Private vacation home Click For Pricing

Only 5 minutes away from Stratton Mountain

Only 5 minutes away from Stratton Mountain

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Winhall Vermont Private vacation home From $900 per night (USD)

Historic 1780 Manchester Farm House With Mountain Views and 7 Bedrooms

Historic 1780 Manchester Farm House With Mountain Views and 7 Bedrooms

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Sunderland Vermont Private vacation home From $629 per night (USD)

NATURE RETREAT BUT MINUTES TO MANCHESTER SHOPS AND SKIING

NATURE RETREAT BUT MINUTES TO MANCHESTER SHOPS AND SKIING

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manchester center Vermont Private vacation home From $179 per night (USD)

Bromley Farmhouse close to skiing and hikes

Bromley Farmhouse close to skiing and hikes

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Peru Vermont Private vacation home From $325 per night (USD)

Ski right onto the mountain from the backyard of our condo building!

Ski right onto the mountain from the backyard of our condo building!

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Peru Vermont Condo From $203 per night (USD)

Tree-lined lodge with deck, fireplaces, porch, game room, & fast WiFi

Tree-lined lodge with deck, fireplaces, porch, game room, & fast WiFi

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Peru Vermont Private vacation home From $291 per night (USD)

$Super Private Estate w\/ Guest Cottage Near Center$

Super Private Estate w\/ Guest Cottage Near Center

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Dorset Vermont Private vacation home From $1276 per night (USD)

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

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

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woodford Vermont Cottage From $175 per night (USD)

Bromley Aframe - King Master Bed, Wood Fireplace

Bromley Aframe - King Master Bed, Wood Fireplace

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Peru Vermont Chalet From $164 per night (USD)

Home with a spring-fed pond and mountain view.

Home with a spring-fed pond and mountain view.

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Manchester Vermont Cottage From $220 per night (USD)

Quintessential Cabin in the Woods near Town

Quintessential Cabin in the Woods near Town

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Dorset Vermont Cabin Click For Pricing

$Secluded, rustic home w\/ private hot tub & immense nature - 5 miles to Stratton$

Secluded, rustic home w\/ private hot tub & immense nature - 5 miles to Stratton

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Winhall Vermont Private vacation home From $139 per night (USD)

Family oriented community in country setting...10 minute walk to town center.

Family oriented community in country setting...10 minute walk to town center.

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Manchester Vermont Private vacation home From $495 per night (USD)

*Wandering Moose* Hot Tub at a Renovated Stratton Home

*Wandering Moose* Hot Tub at a Renovated Stratton Home

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Winhall Vermont Private vacation home From $1491 per night (USD)

2024 Seasonal Summer Rental

2024 Seasonal Summer Rental

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Winhall Vermont Private vacation home From $500 per night (USD)

The Lower Hollow House, dip into river in backyard

The Lower Hollow House, dip into river in backyard

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Dorset Vermont Private vacation home From $705 per night (USD)

Renovated Townhouse next to a Golf Course and Pool

Renovated Townhouse next to a Golf Course and Pool

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Manchester Vermont Private vacation home From $779 per night (USD)

Renovated House with Golf Course | Free Parking

Renovated House with Golf Course | Free Parking

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Manchester Vermont Private vacation home From $1029 per night (USD)

Best Western Bennington - Deluxe King Bed #5

Best Western Bennington - Deluxe King Bed #5

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Bennington Vermont Guest house From $149 per night (USD)

Best Western Bennington - Deluxe King Bed #3

Best Western Bennington - Deluxe King Bed #3

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Bennington Vermont Guest house From $149 per night (USD)

Carriage House Apartment In The Heart Of Manchester, VT—Walk To All!!

Carriage House Apartment In The Heart Of Manchester, VT—Walk To All!!

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Manchester Vermont Guest house From $140 per night (USD)

Best Western Bennington - Deluxe King Bed #2

Best Western Bennington - Deluxe King Bed #2

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Bennington Vermont Guest house From $149 per night (USD)

Best Western Bennington - Deluxe King Bed #4

Best Western Bennington - Deluxe King Bed #4

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Bennington Vermont Guest house From $149 per night (USD)

Best Western Bennington - Deluxe King Bed #1

Best Western Bennington - Deluxe King Bed #1

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Bennington Vermont Guest house From $149 per night (USD)

Bright Bromley Mountain Condo with 2 Balconies!

Bright Bromley Mountain Condo with 2 Balconies!

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Peru Vermont Condo From $180 per night (USD)

$Ski-in\/out family home w\/shared pool\/Ping-pong\/balcony\/free WiFi\/fireplace$

Ski-in\/out family home w\/shared pool\/Ping-pong\/balcony\/free WiFi\/fireplace

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Peru Vermont Condo From $382 per night (USD)

$Beautiful Manchester VT Mountain Retreat w\/Hot Tub$

Beautiful Manchester VT Mountain Retreat w\/Hot Tub

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Winhall Vermont Chalet From $263 per night (USD)

New! Lovingly restored Antique Vermont Farm House- Horse Friendly!

New! Lovingly restored Antique Vermont Farm House- Horse Friendly!

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Rupert Vermont Private vacation home From $700 per night (USD)

A Real Farm Vacation

A Real Farm Vacation

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Bennington Vermont Agritourism Click For Pricing

$Manchester Home on 40 Acres w\/ Game Room & Deck!$

Manchester Home on 40 Acres w\/ Game Room & Deck!

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Manchester Center Vermont Private vacation home From $561 per night (USD)

Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont

Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont

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Manchester Center Vermont Private vacation home From $476 per night (USD)

Newly renovated mountain view close to skiing and horse show

Newly renovated mountain view close to skiing and horse show

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2.0
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Dorset Vermont Private vacation home From $225 per night (USD)

Green Mountain National Forest Ski Chalet

Green Mountain National Forest Ski Chalet

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3.0
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Winhall Vermont Private vacation home From $500 per night (USD)

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