Bennington Rentals
From $265 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 $265 per night (USD)VRBO
From $415 per night (USD)Expedia
Stylish Rustic Retreat w\/ Breathtaking Mtn Views!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Experience true beauty at this Bennington cabin immersed in 100 acres of peaceful seclusion. Only 15 minutes from town, ...
From $415 per night (USD)Expedia
From $271 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 $271 per night (USD)VRBO
From $215 per night (USD)VRBO
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 $215 per night (USD)VRBO
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
Historic Home in Old Bennington, Vermont
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
This lovely family home was built in 1828. The home is furnished with fine antiques. Located on over two acres of gard ...
From $291 per night (USD)VRBO
From $360 per night (USD)Expedia
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 $360 per night (USD)Expedia
From $198 per night (USD)VRBO
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 $198 per night (USD)VRBO
From $145 per night (USD)Expedia
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 $145 per night (USD)Expedia
From $263 per night (USD)VRBO
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 $263 per night (USD)VRBO
From $140 per night (USD)Expedia
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 $140 per night (USD)Expedia
From $377 per night (USD)VRBO
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)VRBO
From $182 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 $182 per night (USD)VRBO
From $190 per night (USD)VRBO
Best Western Bennington - Deluxe King Bed #5
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
AMENITIES: FREE Daily Breakfast, Individual Climate Control, Cable/Satellite TV, Seating Area, Functional Work Desk, Hai ...
From $190 per night (USD)VRBO
From $190 per night (USD)Expedia
Best Western Bennington - Deluxe King Bed #3
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
AMENITIES: FREE Daily Breakfast, Individual Climate Control, Cable/Satellite TV, Seating Area, Functional Work Desk, Hai ...
From $190 per night (USD)Expedia
From $190 per night (USD)VRBO
Best Western Bennington - Deluxe King Bed #2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
AMENITIES: FREE Daily Breakfast, Individual Climate Control, Cable/Satellite TV, Seating Area, Functional Work Desk, Hai ...
From $190 per night (USD)VRBO
From $190 per night (USD)Expedia
Best Western Bennington - Deluxe King Bed #4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
AMENITIES: FREE Daily Breakfast, Individual Climate Control, Cable/Satellite TV, Seating Area, Functional Work Desk, Hai ...
From $190 per night (USD)Expedia
From $190 per night (USD)VRBO
Best Western Bennington - Deluxe King Bed #1
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
AMENITIES: FREE Daily Breakfast, Individual Climate Control, Cable/Satellite TV, Seating Area, Functional Work Desk, Hai ...
From $190 per night (USD)VRBO
From $185 per night (USD)Expedia
Two Brooks Lodge, 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 $185 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 ...
Click For PricingVRBO
From $244 per night (USD)VRBO
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)VRBO
From $310 per night (USD)VRBO
Bright 3-Bedroom Historical Cottage w\/ pool table
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Charming & bright 3-bedroom cottage located across from the authentic covered Henry Bridge! Newly renovated this past s ...
From $310 per night (USD)VRBO
From $315 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 $315 per night (USD)VRBO
From $702 per night (USD)VRBO
Perfect for Leaf Peeping w\/Bar Room, Hot Tub
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 22
Exceptional home with 6 bedrooms, 5 full bathrooms, 2 half bathrooms. Bar room perfect for entertaining guests. Game roo ...
From $702 per night (USD)VRBO
From $240 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 $240 per night (USD)Expedia
From $693 per night (USD)VRBO
New Fire Pit & Game Room, Mtn Views, Fully Loaded
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Newly Renovated Cape with Function, Comfort, & Style This amazing 5 bedroom 4 bath Cape Cod has been completely renovat ...
From $693 per night (USD)VRBO
From $251 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 $251 per night (USD)Expedia
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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 ...
Click For PricingVRBO
From $262 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 $262 per night (USD)Expedia
From $219 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 $219 per night (USD)VRBO
From $204 per night (USD)VRBO
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 $204 per night (USD)VRBO
From $299 per night (USD)VRBO
The Vermont Farmhouse. Gorgeous Countryside. Hiking Trails. Skiing. Dog Friendly
- 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 $299 per night (USD)VRBO