Bennington Rentals
From $278 per night (USD)VRBO
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Spend the month, week or weekend in a beautiful rustic converted barn on 6.5 very private sunny country acres with south ...
From $278 per night (USD)VRBO
From $418 per night (USD)Expedia
Breathtaking Mtn Views: Stylish Rustic Retreat!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
2,000 Sq Ft | Pet Friendly w/ Fee | Fire Pit | Outdoor Shower (Open May-October) | Antique Oak Flooring | Gas Grill Exp ...
From $418 per night (USD)Expedia
From $274 per night (USD)VRBO
Bennington Guest Farm
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Large Gracious Victorian Farmhouse lovingly restored to accommodate nine guests in a quaint relaxed atmosphere. Conveni ...
From $274 per night (USD)VRBO
From $224 per night (USD)Expedia
1920's Bennington Vermont Guest Barn
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
Very comfortable accommodations with just about everything brand new down to quality mattresses and bedding. New kitchen ...
From $224 per night (USD)Expedia
From $244 per night (USD)VRBO
Downtown Victorian House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Fully furnished first floor apartment located in a recently renovated Victorian House. The large living room boasts a f ...
From $244 per night (USD)VRBO
From $284 per night (USD)Expedia
Luxury Living High Above the Center of Town.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Breathtaking views up & down Main Street. In the heart of downtown Bennington, steps from the four corners of US Rte 7 a ...
From $284 per night (USD)Expedia
From $291 per night (USD)VRBO
Victorian Home in Bennington, Vermont
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
This home was originally built in the mid-1800's. It has been completely remodeled to preserve the historic beauty of t ...
From $291 per night (USD)VRBO
From $178 per night (USD)Expedia
Traveler Dream Space in the Center of Downtown Bennington Steps From Everything!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Whether you're coming to Bennington for the fall colors, winter sports, spring graduations, summer street festivals and ...
From $178 per night (USD)Expedia
From $131 per night (USD)VRBO
Cozy 1 Bedroom farm stay cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This cozy 1 bedroom cottage unit is located on a casual farm. Get a little taste of Vermont Country Living . Chickens, t ...
From $131 per night (USD)VRBO
From $281 per night (USD)Expedia
Victorian mansion's Jim-Dandy Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
Situated on the first floor of the Carriage House, this elegant and spacious room was once the abode of the original own ...
From $281 per night (USD)Expedia
From $111 per night (USD)VRBO
Studio style farm stay
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This cozy one bedroom is located on a country farm setting. Once used as a Gardner’s quarters. Quarters are private but ...
From $111 per night (USD)VRBO
From $377 per night (USD)Expedia
The Henry House & Authentic Red Covered Bridge!
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 10
Built in 1769, the house of Lt. William Henry, Revolutionary War Hero and participant in the Battle of Bennington, is li ...
From $377 per night (USD)Expedia
From $417 per night (USD)VRBO
Cozy Ski retreat with new Pet 🦮 Yard and many upgrades! Close to 3 Ski areas!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Nestled on a private 5 acres lot on the border of NY and Vermont this home is in the country but close to all the amenit ...
From $417 per night (USD)VRBO
From $272 per night (USD)Expedia
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
This scenic home is located in the quaint, historic town of Bennington, Vermont. Sit in the hot tub and enjoy the soothi ...
From $272 per night (USD)Expedia
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A Real Farm Vacation
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
White Rock Farm is a 295-acre working farm in Bennington VT, a three hour drive from New York or Boston. it is part of t ...
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From $244 per night (USD)Expedia
Spacious 2nd floor apartment steps from popular corner market.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located in a charming 1890's colonial home, this 2nd floor apartment has a convenient in town location that is close to ...
From $244 per night (USD)Expedia
From $322 per night (USD)VRBO
Cozy one of a kind renovated Barn-ultimate getaway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Welcome to The Barn Retreat – where comfort, adventure, and relaxation seamlessly intertwine. Book your stay today and c ...
From $322 per night (USD)VRBO
From $1013 per night (USD)Expedia
Historic Downtown Home w\/Bar Room, Hot Tub
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 22
🏡Historic home with 6 bedrooms, 5.5 bathrooms 🍸Bar room perfect for entertaining guests. 🎮Game room, complete with an ...
From $1013 per night (USD)Expedia
From $286 per night (USD)VRBO
Short walk to Main St. and SVMC and under 1 hour to skiing.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
This house comes fully furnished with linens, dishes, washer/dryer, WiFi and 3 Roku TVs. It has 2 bedrooms, 2.5 baths a ...
From $286 per night (USD)VRBO
From $259 per night (USD)Expedia
Victorian mansions Coach Room with Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
The estate, formerly the private residence of Louis A. Graves, was the creation of architect William C. Bull who designe ...
From $259 per night (USD)Expedia
From $711 per night (USD)VRBO
Mtn Views, 3 King Beds, Game Room, Chef's Kitchen
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Tired of run-down houses? Bennington's Green Mountain Escape is the place for you! Bennington’s Green Mountain Escape ...
From $711 per night (USD)VRBO
From $224 per night (USD)Expedia
Bennington Home w\/ Deck ~ 5 Mi to Bald Mountain!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 7
Just 2 miles from the Downtown Bennington Historic District, this 3-bed, 2-bath vacation rental in Vermont’s first town ...
From $224 per night (USD)Expedia
Click For PricingVRBO
Perfect stylish VT cabin with fast & reliable wifi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
About this space Dreamy Vermont log home tucked away in the woods but close to the conveniences of town. Charming, and m ...
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From $280 per night (USD)Expedia
Mountain Sanctuary Dome Rustic Solitude 5BR
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Where simplicity meets solitude. Find connection in this scenic mountainous retreat. Enmeshed in the natural landscape, ...
From $280 per night (USD)Expedia
From $190 per night (USD)VRBO
Bennington Gem w\/ Smart TV Near Historic District!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Immerse yourself in a relaxing retreat at this 1-bedroom, 1-bathroom vacation rental nestled in the heart of Bennington, ...
From $190 per night (USD)VRBO
From $362 per night (USD)Expedia
Green Mountain Getaway
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to the serene Green Mountain Getaway, nestled in the picturesque town of Bennington. This charming Apartment offe ...
From $362 per night (USD)Expedia
From $400 per night (USD)VRBO
The Vermont Farmhouse + Stunning Views + Dog Friendly + Adjacent Nature Preserve
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to this lovingly restored 1860s Vermont farmhouse, where historic charm meets modern comfort. With 2 cozy bedroo ...
From $400 per night (USD)VRBO
From $155 per night (USD)Expedia
Charming 2-bedroom apartment in superb Bennington with WiFi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Unwind in Bennington at this delightful apartment. With 2 bedrooms including 1 queen bed, 1 twin bed, and 1 full bed, th ...
From $155 per night (USD)Expedia
From $319 per night (USD)VRBO
NEW!! Renovated historic 3 BR 2 full BA. Walkable to downtown. Restaurants\/Shops
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Step into a piece of Bennington history with this beautifully renovated historic home, nestled in the heart of downtown. ...
From $319 per night (USD)VRBO
From $217 per night (USD)Expedia
Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Shopkeeper's Oasis is a property on the state historic register right in the center of downtown Bennington. The for ...
From $217 per night (USD)Expedia
From $153 per night (USD)VRBO
Cozy Loft steps from VT Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This third floor loft apartment is walking distance from Historic Old Bennington and the downtown proper. Enjoy local sh ...
From $153 per night (USD)VRBO