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
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Bennington vacation homes

A wooden kitchen with a central island, bar stools, and a dining table with chairs.

1. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (13 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 ￥18,317
￥32,177 total
includes taxes & fees
Nov 1 - Nov 2
Cozy Home in Pownal VT
A two-story house with a red roof, a front porch with a railing, and a gravel driveway.

2. 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 ￥21,228
￥90,563 total
includes taxes & fees
Nov 9 - Nov 10
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
Exterior

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

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

4. Long Trail House 368 condo in Stratton Village, walk to the lifts

Long Trail House 368 condo in Stratton Village, walk to the lifts
Stratton
The price is ￥11,762
￥40,402 total
includes taxes & fees
Nov 4 - Nov 5
Long Trail House 368 condo in Stratton Village, walk to the lifts
A room with a large window, a wooden table, two chairs, and a woven basket on the table.

5. 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, (4 reviews)
"Beautiful accommodations. Great communication with host."
United States
Peggy S.
The price is ￥42,657
￥97,303 total
includes taxes & fees
Nov 1 - Nov 2
Cozy 3 Bedroom Condo in the Heart of Manchester VT
A spacious kitchen with a central island, stainless steel appliances, and pendant lighting.

6. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
1812 House, 2 Stays, 1 home
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 ￥31,179
￥116,890 total
includes taxes & fees
Nov 1 - Nov 2
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A street view at dusk with a restaurant and a shop with a mannequin in the window.

8. 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.
The price is ￥56,876
￥84,622 total
includes taxes & fees
Nov 1 - Nov 2
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

9. 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 ￥50,557
￥130,326 total
includes taxes & fees
Nov 9 - Nov 10
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A two-story white house with a front porch, a door with a wreath, and a chimney.

10. 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.
Cozy farmhouse in Manchester - short drive to multiple ski mountains!
A rustic interior with a wooden ceiling, a bar area with stools, a sofa, and a dining table.

11. Wonderful hilltop house with breathtaking views

Wonderful hilltop house with breathtaking views
Dorset
Wonderful hilltop house with breathtaking views
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)
"enjoyed our week at this property"
United States
cory p.
The price is ￥29,677
￥61,835 total
includes taxes & fees
Oct 30 - Oct 31
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

13. 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 ￥50,975
￥101,620 total
includes taxes & fees
Oct 31 - Nov 1
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A cabin with a sloped roof, large windows, and a balcony with outdoor seating.

14. 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, (27 reviews)
"Great cabin , so cozy with the wood burning stove "
United States
Susan f.
The price is ￥32,374
￥60,279 total
includes taxes & fees
Nov 8 - Nov 9
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
Eatery

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

Amanita Dome. All-inclusive food and drinks.
Cambridge
The price is ￥47,397
￥98,079 total
includes taxes & fees
Nov 1 - Nov 2
Amanita Dome. All-inclusive food and drinks.
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

16. 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 ￥30,923
￥90,274 total
includes taxes & fees
Nov 4 - Nov 5
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
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.

17. 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.
The price is ￥19,196
￥65,612 total
includes taxes & fees
Nov 1 - Nov 2
Modern Mount Snow Gnarvana - Steps to Carinthia
A deck with two wicker chairs and a string of lights against a backdrop of trees and a sunset.

18. 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 ￥24,297
￥31,021 total
includes taxes & fees
Nov 4 - Nov 5
The Eagles Wing at The CHM - Private Apartment
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 ￥36,129
￥75,955 total
includes taxes & fees
Oct 30 - Oct 31
A roomy remodeled retreat close to MassMoCA
A log cabin with a balcony, surrounded by snow-covered trees and a wind turbine in the background.

20. Greylock Cabin

Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"This is a beautiful cabin on an amazing property with a great view of Mt Greylock! Clean, comfortable, great location, communication with the owner was outstanding and questions were answered quickly. It all went smoothly and we highly recommend this property!"
United States
Margaret M.
The price is ￥45,359
￥74,068 total
includes taxes & fees
Nov 1 - Nov 2
Greylock Cabin
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

Hampton Inn Bennington

Hampton Inn Bennington

10/10 Excellent
"Breakfast had cooked oatmeal And had 3 main items for breakfast each day"
paul 2-night trip
Posted 4 days ago
Hampton Inn Bennington

Find out more about Bennington

Bennington Vacation Homes information

Number of reviews
360
Accommodation
257 Vacation Homes
Lowest Price
￥31,021
Highest Price
￥130,326