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)
"enjoyed our week at this property"
United States
cory p.
The price is £297
includes taxes & fees
10 Nov - 11 Nov
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
A two-story house with a porch, surrounded by trees and snow.

2. 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 £231
includes taxes & fees
1 Nov - 2 Nov
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
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 £318
includes taxes & fees
29 Oct - 30 Oct
East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub
A two-story house with a red roof, a front porch with a railing, and a gravel driveway.

4. 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 £440
includes taxes & fees
9 Nov - 10 Nov
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

5. 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

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

Amanita Dome. All-inclusive food and drinks.
Cambridge
The price is £469
includes taxes & fees
10 Nov - 11 Nov
Amanita Dome. All-inclusive food and drinks.
A cabin with a sloped roof, large windows, and a balcony with outdoor seating.

7. 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 £286
includes taxes & fees
29 Oct - 30 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.

8. 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 £421
includes taxes & fees
29 Oct - 30 Oct
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
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 £300
includes taxes & fees
29 Oct - 30 Oct
Modern Mount Snow Gnarvana - Steps to Carinthia
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

10. 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 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 £438
includes taxes & fees
10 Nov - 11 Nov
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A log cabin with a balcony, surrounded by snow-covered trees and a wind turbine in the background.

12. 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 kitchen with white cabinets, a wooden dining table, and pendant lights.

13. 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 £354
includes taxes & fees
29 Oct - 30 Oct
A roomy remodeled retreat close to MassMoCA
A room with a large window, a wooden table, two chairs, and a woven basket on the table.

14. 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 £467
includes taxes & fees
1 Nov - 2 Nov
Cozy 3 Bedroom Condo in the Heart of Manchester VT
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 £439
includes taxes & fees
29 Oct - 30 Oct
Experience Vermont’s Fall Magic at here at the Lemondrop
A spacious kitchen with a central island, stainless steel appliances, and pendant lighting.

16. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is £621
includes taxes & fees
10 Nov - 11 Nov
1812 House, 2 Stays, 1 home
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

17. 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 £548
includes taxes & fees
2 Nov - 3 Nov
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A spacious kitchen with a large island, wooden ceiling beams, and a view to the outside.

18. 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 modern kitchen with a built-in fireplace, wine storage, and a dining area with wooden furniture.

19. 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
3 Nov - 4 Nov
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
A street view at dusk with a restaurant and a shop with a mannequin in the window.

20. 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 £409
includes taxes & fees
29 Oct - 30 Oct
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
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

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good
"The room was clean and the staff was friendly and helpful. Lots of parking . The hot tub was nice after a day of biking."
Kathleen 2-night trip
Posted less than an hour ago
Hotel Downstreet, an Ascend Collection Hotel

Find out more about North Bennington

North Bennington Holiday Homes information

Number of reviews
438
Accommodation
503 Holiday Homes
Lowest Price
£158
Highest Price
£878