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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Bennington holiday 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 £270
includes taxes & fees
20 Oct - 21 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, (10 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is £159
includes taxes & fees
21 Oct - 22 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 £319
includes taxes & fees
19 Oct - 20 Oct
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

4. 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 £200
includes taxes & fees
19 Oct - 20 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.

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, (2 reviews)
"Beautiful place Very spacious and super organized we love our stay "
United States
Rafael
The price is £469
includes taxes & fees
22 Oct - 23 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.

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

Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Winhall
9.4 out of 10, Exceptional, (43 reviews)
"Our family had a wonderful vacation. The house and location were great. We will come back."
United States
Victoria L.
The price is £484
includes taxes & fees
19 Oct - 20 Oct
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A spacious kitchen with a central island, stainless steel appliances, and pendant lighting.

7. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is £553
includes taxes & fees
3 Nov - 4 Nov
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.

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 £418
includes taxes & fees
29 Oct - 30 Oct
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
A modern two-story house with a front porch, a staircase, and a driveway.

9. Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Jamaica
9.6 out of 10, Exceptional, (30 reviews)
"House was perfect for a guys trip for skiing. Just as expected. Would stay again. "
United States
Michael A.
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

10. 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 £636
includes taxes & fees
19 Oct - 20 Oct
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.

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 £558
includes taxes & fees
26 Oct - 27 Oct
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 £295
includes taxes & fees
20 Oct - 21 Oct
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Miscellaneous

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 £115
includes taxes & fees
18 Oct - 19 Oct
Runamuk Farm Camp Tiny House near Cambridge, New York
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, (25 reviews)
"Great cabin , so cozy with the wood burning stove "
United States
Susan f.
The price is £266
includes taxes & fees
19 Oct - 20 Oct
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

15. 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 £468
includes taxes & fees
18 Oct - 19 Oct
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
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 £474
includes taxes & fees
26 Oct - 27 Oct
Amanita Dome. All-inclusive food and drinks.
A bedroom with a large bed, a window with blinds, a bookshelf, and a wall-mounted ship's wheel.

17. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.6 out of 10, Exceptional, (5 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is £127
includes taxes & fees
19 Oct - 20 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 £440
includes taxes & fees
27 Oct - 28 Oct
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

19. 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 £332
includes taxes & fees
12 Nov - 13 Nov
Greylock Cabin
A kitchen with white cabinets, a wooden dining table, and pendant lights.

20. 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 £355
includes taxes & fees
20 Oct - 21 Oct
A roomy remodeled retreat close to MassMoCA
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
"Overnight stay Nice break from a long drive."
Randy 1-night trip
Posted 3 days ago
Hampton Inn Bennington

Find out more about Bennington

Bennington Holiday Homes information

Number of reviews
312
Accommodation
257 Holiday Homes
Lowest Price
£115
Highest Price
£636