A covered bridge with a sign reading "Silk Road Bridge" and a height restriction of 10 feet 6 inches.

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Bennington vacation homes

A two-story house with a porch, surrounded by trees and snow.

1. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Bennington
8.6 out of 10, Excellent, (36 reviews)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
The price is AED 650
AED 1,389 total
includes taxes & fees
23 Oct - 24 Oct
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

2. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (12 reviews)
"Absolutely wonderful place to stay. Quiet, clean, comfortable and close to a lot of things while feeling secluded. Owner communicated quickly and entry was easy. Loved every minute of our stay."
United States
Jeri R.
The price is AED 426
AED 753 total
includes taxes & fees
26 Oct - 27 Oct
Cozy Home in Pownal VT
A bedroom with a bed, bedside tables, a window, and a radiator.

3. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
Woodford
10.0 out of 10, Exceptional, (1 review)
"Enjoyed our stay! Very clean and comfortable."
United States
Dana W.
The price is AED 623
AED 1,657 total
includes taxes & fees
16 Nov - 17 Nov
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A bedroom with a bed, a nightstand, a lamp, a chair, and a window.

4. East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub

East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub
Bennington
The price is AED 1,194
AED 1,530 total
includes taxes & fees
26 Oct - 27 Oct
East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

5. Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Stratton
The price is AED 274
AED 941 total
includes taxes & fees
25 Oct - 26 Oct
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A room with a large window, a wooden table, two chairs, and a woven basket on the table.

6. Cozy 3 Bedroom Condo in the Heart of Manchester VT

Cozy 3 Bedroom Condo in the Heart of Manchester VT
Manchester
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful accommodations. Great communication with host."
United States
Peggy S.
The price is AED 992
AED 2,262 total
includes taxes & fees
25 Oct - 26 Oct
Cozy 3 Bedroom Condo in the Heart of Manchester VT
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

7. Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Winhall
9.2 out of 10, Wonderful, (44 reviews)
"Our family had a wonderful vacation. The house and location were great. We will come back."
United States
Victoria L.
The price is AED 725
AED 2,435 total
includes taxes & fees
26 Oct - 27 Oct
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

8. Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Winhall
10.0 out of 10, Exceptional, (15 reviews)
"Clean, lots of room, easy access to Stratton, responsive host."
United States
Mark H.
The price is AED 1,194
AED 3,084 total
includes taxes & fees
1 Nov - 2 Nov
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A spacious kitchen with a central island, stainless steel appliances, and pendant lighting.

9. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is AED 1,025
AED 2,748 total
includes taxes & fees
27 Oct - 28 Oct
1812 House, 2 Stays, 1 home
An outdoor dining area with tables and umbrellas, a wooden fence, and a building with large windows and lights.

10. Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.

Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
Manchester
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful cozy house with plenty of beds and space. We drove here in a snowstorm and were so thankful that the host had cleared the driveway and walkways for us. Overall a great stay."
United States
Greg W.
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
A two-story white house with a front porch, a door with a wreath, and a chimney.

11. Cozy farmhouse in Manchester - short drive to multiple ski mountains!

Cozy farmhouse in Manchester - short drive to multiple ski mountains!
Manchester
9.4 out of 10, Exceptional, (3 reviews)
"The hosts were very friendly and responsive during our stay. Loved that the house is close to the main town as well as close to the ski slopes (Bromley). "
United States
Marissa H.
The price is AED 1,543
AED 2,943 total
includes taxes & fees
21 Nov - 22 Nov
Cozy farmhouse in Manchester - short drive to multiple ski mountains!
A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.

12. Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Hoosick Falls
9.8 out of 10, Exceptional, (117 reviews)
"This is the third time we’ve stayed at this lovely home and it’s always a treat! Very clean, with a Well stocked kitchen, comfy beds and huge back yard plus a fenced in portion, your dog will love-close to Bennington and walking trails with lots to do. A home away from home! "
United States
Anita T.
The price is AED 691
AED 1,440 total
includes taxes & fees
22 Oct - 23 Oct
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Room

13. Runamuk Farm Camp Tiny House near Cambridge, New York

Runamuk Farm Camp Tiny House near Cambridge, New York
Cambridge
10.0 out of 10, Exceptional, (4 reviews)
"Phenomenal site, with stunning views. Highly recommend!"
United States
Jess M.
The price is AED 461
AED 542 total
includes taxes & fees
22 Oct - 23 Oct
Runamuk Farm Camp Tiny House near Cambridge, New York
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

14. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
The price is AED 1,116
AED 2,273 total
includes taxes & fees
26 Oct - 27 Oct
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A cabin with a sloped roof, large windows, and a balcony with outdoor seating.

15. Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views

Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
shushan
9.6 out of 10, Exceptional, (26 reviews)
"Great cabin , so cozy with the wood burning stove "
United States
Susan f.
The price is AED 658
AED 1,285 total
includes taxes & fees
22 Oct - 23 Oct
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
A snow-covered forest with a geodesic dome structure featuring a central fire.

16. Amanita Dome. All-inclusive food and drinks.

Amanita Dome. All-inclusive food and drinks.
Cambridge
The price is AED 1,102
AED 2,280 total
includes taxes & fees
26 Oct - 27 Oct
Amanita Dome. All-inclusive food and drinks.
A deck with two wicker chairs and a string of lights against a backdrop of trees and a sunset.

17. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.8 out of 10, Exceptional, (6 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is AED 544
AED 697 total
includes taxes & fees
23 Oct - 24 Oct
The Eagles Wing at The CHM - Private Apartment
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

18. VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Wilmington
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful home and property with quick access to a clubhouse with a gym, indoor and outdoor pools, and hot tub. Great for our family trip (including two kids) and lots of games/entertainment for the kids. The house had everything we needed (including kitchenware needed for cooking and preparing food)."
United States
Natalie
The price is AED 1,304
AED 2,828 total
includes taxes & fees
31 Oct - 1 Nov
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A kitchen with white cabinets, a wooden dining table, and pendant lights.

19. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (61 reviews)
"Cute and comfy home. We enjoyed the unique decor and lack of TVs everywhere. It was a great break from all the crazy. Lots of conversation and togetherness."
United States
Diane
The price is AED 841
AED 1,764 total
includes taxes & fees
30 Oct - 31 Oct
A roomy remodeled retreat close to MassMoCA
A spacious indoor area with multiple wooden tables and green chairs, large windows offering a view of a snowy mountain, and a stone fireplace with a fire.

20. Modern Mount Snow Gnarvana - Steps to Carinthia

Modern Mount Snow Gnarvana - Steps to Carinthia
Dover
10.0 out of 10, Exceptional, (26 reviews)
"Perfect for our getaway, convenient for getting to the slopes and a beautiful area to visit"
United States
Lynn B.
Modern Mount Snow Gnarvana - Steps to Carinthia
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Bennington Hotel Reviews

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

8/10 Good
"Nice place, good breakfast. No elevator was the biggest problem."
JANET 1-night trip
Posted 3 hours ago
Hotel Vervana, Trademark Collection by Wyndham

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