A wooden gazebo with a roof, surrounded by trees and a wooden walkway.

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Check prices for these dates

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

Our top choices for North Bennington holiday homes

A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.

1. 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 £294
includes taxes & fees
29 Oct - 30 Oct
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
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 £430
includes taxes & fees
16 Nov - 17 Nov
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
The price is £317
includes taxes & fees
29 Oct - 30 Oct
East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

4. 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 £158
includes taxes & fees
29 Oct - 30 Oct
Cozy Home in Pownal VT
Eatery

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

Amanita Dome. All-inclusive food and drinks.
Cambridge
The price is £471
includes taxes & fees
1 Nov - 2 Nov
Amanita Dome. All-inclusive food and drinks.
A cabin with a sloped roof, large windows, and a balcony with outdoor seating.

6. 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 £265
includes taxes & fees
1 Nov - 2 Nov
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.

7. 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 £420
includes taxes & fees
29 Oct - 30 Oct
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

8. 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 £199
includes taxes & fees
4 Nov - 5 Nov
Long Trail House 368 condo in Stratton Village, walk to the lifts
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.

9. 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 £299
includes taxes & fees
29 Oct - 30 Oct
Modern Mount Snow Gnarvana - Steps to Carinthia
A kitchen with white cabinets, a wooden dining table, and pendant lights.

10. 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 £353
includes taxes & fees
30 Oct - 31 Oct
A roomy remodeled retreat close to MassMoCA
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

11. 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 £431
includes taxes & fees
29 Oct - 30 Oct
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A room with a large window, a wooden table, two chairs, and a woven basket on the table.

12. 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 £466
includes taxes & fees
1 Nov - 2 Nov
Cozy 3 Bedroom Condo in the Heart of Manchester VT
A log cabin with a balcony, surrounded by snow-covered trees and a wind turbine in the background.

13. 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 £357
includes taxes & fees
1 Nov - 2 Nov
Greylock Cabin
A spacious kitchen with a central island, stainless steel appliances, and pendant lighting.

14. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is £567
includes taxes & fees
3 Nov - 4 Nov
1812 House, 2 Stays, 1 home
A spacious living room with a fireplace, a dining area, and a kitchen with wooden cabinets and a microwave.

15. Experience Vermont’s Fall Magic at here at the Lemondrop

Experience Vermont’s Fall Magic at here at the Lemondrop
Dover
10.0 out of 10, Exceptional, (46 reviews)
"Lovely house - perfect for a ski trip!"
United States
Alexander H.
The price is £437
includes taxes & fees
29 Oct - 30 Oct
Experience Vermont’s Fall Magic at here at the Lemondrop
A modern kitchen with a built-in fireplace, wine storage, and a dining area with wooden furniture.

16. Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Dover
10.0 out of 10, Exceptional, (14 reviews)
"great location easy access to the mountain and the pool was outstanding."
United States
jim f.
The price is £878
includes taxes & fees
29 Oct - 30 Oct
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
A spacious kitchen with a large island, wooden ceiling beams, and a view to the outside.

17. 5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton

5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton
Stratton
10.0 out of 10, Exceptional, (20 reviews)
"Great spot for a large group. "
United States
Brian G.
The price is £769
includes taxes & fees
9 Nov - 10 Nov
5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton
A street view at dusk with a restaurant and a shop with a mannequin in the window.

18. 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 £408
includes taxes & fees
29 Oct - 30 Oct
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

19. 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 £547
includes taxes & fees
1 Nov - 2 Nov
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A spacious living room with a fireplace, leather furniture, wooden beams, and a cityscape painting.

20. Walk To Town, Hottub, Firepit, Games, Mt Snow

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (65 reviews)
"Beautiful house, amazing location, helpful and responsive hosts."
United States
Jeremy P.
The price is £593
includes taxes & fees
29 Oct - 30 Oct
Walk To Town, Hottub, Firepit, Games, Mt Snow
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 North Bennington Hotel Reviews

The Williams Inn

The Williams Inn

10/10 Excellent
"It's always a joy to return to Williamstown and to the Williams Inn. It's a lovely, peaceful place. Rooms are spacious and beautifully designed and decorated."
David 1-night trip
Posted 12 hours ago
The Williams Inn

Find out more about North Bennington

North Bennington Holiday Homes information

Number of reviews
467
Accommodation
503 Holiday Homes
Lowest Price
£158
Highest Price
£878