Photo by Laury Kelly

Holiday Homes in North Bennington

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Find holiday rentals that suit your style

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Apartments
Apartments
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Cabins
Cabins

Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for North Bennington holiday homes

A wooden bear statue with a 'WELCOME' sign in front of a garden with various plants and a stone pathway.

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, (120 reviews)
"enjoyed our week at this property"
United States
cory p.
The price is NZ$663
includes taxes & fees
15 Nov - 16 Nov
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
A room with a sliding glass door leading to an outdoor deck with a red railing and a wicker chair.

2. Red Country Escape with Mountain Views

Red Country Escape with Mountain Views
Eagle Bridge
9.6 out of 10, Exceptional, (9 reviews)
"The house is a very cute cottage with a large back yard suitable for kids and pets. The house itself is clean and well stocked. Very pet-friendly, host is easy to reach, and the kitchen is well supplied. Had a very nice time there."
United States
Susan M.
The price is NZ$603
includes taxes & fees
15 Nov - 16 Nov
Red Country Escape with Mountain Views
A covered porch with wooden beams, a pool, and chairs.

3. West Barn Suite at Hubbell Homestead - Mountain Views & Jetted Tub

West Barn Suite at Hubbell Homestead - Mountain Views & Jetted Tub
Bennington
The price is NZ$471
includes taxes & fees
26 Nov - 27 Nov
West Barn Suite at Hubbell Homestead - Mountain Views & Jetted Tub
A two-story house with a porch, surrounded by trees and snow.

4. 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 NZ$514
includes taxes & fees
15 Nov - 16 Nov
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
A covered porch with wooden beams, a pool, and chairs.

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

East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub
Bennington
The price is NZ$471
includes taxes & fees
26 Nov - 27 Nov
East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub
A modern living room with a flat-screen TV, wooden flooring, a gray sofa, and a kitchen in the background.

6. 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 NZ$943
includes taxes & fees
16 Nov - 17 Nov
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
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 NZ$649
includes taxes & fees
15 Nov - 16 Nov
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

8. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (15 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 NZ$350
includes taxes & fees
24 Nov - 25 Nov
Cozy Home in Pownal VT
Dome exterior

9. Amanita Dome. Inclusive Brunch & Dinner Experience

Amanita Dome. Inclusive Brunch & Dinner Experience
Cambridge
The price is NZ$1,060
includes taxes & fees
23 Nov - 24 Nov
Amanita Dome. Inclusive Brunch & Dinner Experience
A rustic cabin with a dirt path leading to it, surrounded by trees.

10. Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown

Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown
Pownal
10.0 out of 10, Exceptional, (41 reviews)
"We enjoyed our stay! The home was clean, well-stocked, and very comfortable. I loved the serenity of the location. We took walks on trails through the forest and enjoyed the peace and quiet."
United States
Claudette R.
The price is NZ$1,129
includes taxes & fees
9 Dec - 10 Dec
Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown
A residential house with a blue exterior, a black fence, and a large tree in the background.

11. 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 NZ$977
includes taxes & fees
29 Nov - 30 Nov
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

12. 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 NZ$471
includes taxes & fees
16 Nov - 17 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.

13. 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 NZ$1,117
includes taxes & fees
19 Nov - 20 Nov
Modern Mount Snow Gnarvana - Steps to Carinthia
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

14. Home on Hudson4 bedroom

Home on Hudson4 bedroom
Stillwater
10.0 out of 10, Exceptional, (1 review)
"Great space, wonderful kitchen, bonus of large fenced yard for the dog and an amazing river view! Owners were very communicative and a pleasure to work with!"
United States
Dina F.
The price is NZ$803
includes taxes & fees
16 Nov - 17 Nov
Home on Hudson4 bedroom
A wooden swing set with two cushioned swings in a natural setting with trees and a cabin in the background.

15. 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 NZ$831
includes taxes & fees
15 Dec - 16 Dec
Greylock Cabin
A kitchen with white cabinets, a wooden dining table, and pendant lights.

16. 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 NZ$872
includes taxes & fees
14 Dec - 15 Dec
A roomy remodeled retreat close to MassMoCA
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

17. 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 NZ$933
includes taxes & fees
16 Nov - 17 Nov
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.

18. 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 NZ$1,017
includes taxes & fees
15 Nov - 16 Nov
Cozy 3 Bedroom Condo in the Heart of Manchester VT
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 NZ$1,843
includes taxes & fees
17 Nov - 18 Nov
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
A large house with a driveway, surrounded by lush green trees and a mountain in the background.

20. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is NZ$1,295
includes taxes & fees
1 Dec - 2 Dec
1812 House, 2 Stays, 1 home
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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Learn more about North Bennington

Explore the historic Park-McCullough House with its Victorian architecture and sprawling gardens that transport you to another era. Grab a coffee at Powers Market before wandering the trails of Mile-Around Woods where locals enjoy peaceful morning walks.

See all hotels in North Bennington
A red covered bridge over a river, surrounded by greenery and trees.
Photo by Laury Kelly
Open Photo by Laury Kelly

Top reviews in North Bennington

A bedroom with a fireplace, two beds, a chair, and a nightstand.
The Manchester View

The Manchester View

The Manchester View
Manchester Center

10/10 Excellent

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Australia
Sharon
Reviewed October 15, 2023
The Manchester View