Bennington Rentals
From $198 per night (USD)VRBO
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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 $198 per night (USD)VRBO
From $328 per night (USD)Expedia
Bennington Cabin w\/ Deck & Views of 3 States!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience true beauty at this 100-acre ‘Big Sky’ vacation rental. This secluded cabin is immersed in nature, making it ...
From $328 per night (USD)Expedia
From $219 per night (USD)VRBO
Bennington Guest Farm
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 9
Large Gracious Victorian Farmhouse lovingly restored to accommodate nine guests in a quaint relaxed atmosphere. Conveni ...
From $219 per night (USD)VRBO
From $158 per night (USD)VRBO
1920's Bennington Vermont Guest Barn
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Very comfortable accommodations with just about everything brand new down to quality mattresses and bedding. New kitchen ...
From $158 per night (USD)VRBO
From $199 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 $199 per night (USD)VRBO
From $187 per night (USD)VRBO
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 $187 per night (USD)VRBO
From $260 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 $260 per night (USD)VRBO
From $288 per night (USD)Expedia
Victorian Home in Bennington, Vermont
- Bedrooms:
- 3
- Bathrooms:
- 3
- 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 $288 per night (USD)Expedia
From $139 per night (USD)VRBO
Traveler Dream Space in the Center of Downtown Bennington Steps From Everything!
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 3
Whether you're coming to Bennington for the fall colors, winter sports, spring graduations, summer street festivals and ...
From $139 per night (USD)VRBO
From $113 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 $113 per night (USD)Expedia
From $245 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 $245 per night (USD)VRBO
From $110 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 $110 per night (USD)Expedia
From $299 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 $299 per night (USD)VRBO
From $129 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 $129 per night (USD)VRBO
From $149 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 $149 per night (USD)VRBO
From $149 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 $149 per night (USD)Expedia
From $149 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 $149 per night (USD)VRBO
From $149 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 $149 per night (USD)Expedia
From $149 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 $149 per night (USD)VRBO
From $191 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 soo ...
From $191 per night (USD)Expedia
Click For PricingVRBO
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 $199 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 $199 per night (USD)VRBO
From $249 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 $249 per night (USD)VRBO
From $240 per night (USD)VRBO
Ultimate Getaway- Renovated Barn- a unique one of a kind cozy experiece
- 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 $240 per night (USD)VRBO
From $400 per night (USD)VRBO
Historic Inn w\/Bar Room, Hot Tub, 6 Bedrooms
- 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 $400 per night (USD)VRBO
Click For PricingExpedia
Beautiful Farmhouse in Southern Vermont
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled in the foothills of the Green Mountains in Southern Vermont, the Mile Around Farmhouse is the ideal country retr ...
Click For PricingExpedia
Click For PricingExpedia
Short walk to Four Corners and Medical Center. 40 minute drive to Stratton.
- 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 ...
Click For PricingExpedia
From $165 per night (USD)Expedia
3 bedroom duplex, private setting close to town
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Quiet residential area with a patio, garden and running river. You will always hear the water and birds, very peaceful, ...
From $165 per night (USD)Expedia
From $225 per night (USD)VRBO
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 $225 per night (USD)VRBO
From $123 per night (USD)Expedia
Escape to Serenity: Cozy 3 bedroom apartment
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the Cozy Getaway, a newly renovated 3-bedroom condo on Branch Street in beautiful Bennington, Vermont. This c ...
From $123 per night (USD)Expedia
From $487 per night (USD)VRBO
King Beds, Mountain Views, Chef's Kitchen
- 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 $487 per night (USD)VRBO
From $344 per night (USD)Expedia
Bennington Home w\/ Deck ~ 5 Mi to Bald Mountain!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Just 2 miles from the Downtown Bennington Historic District, this 3-bed, 2-bath vacation rental in Vermont’s first town ...
From $344 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 ...
Click For PricingVRBO