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

Holiday Homes in North Bennington

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

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, (115 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 AU$560
includes taxes & fees
6 Oct - 7 Oct
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
A bedroom with a bed, bedside tables, a window, and a radiator.

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
The price is AU$592
includes taxes & fees
6 Oct - 7 Oct
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.

3. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (9 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 AU$296
includes taxes & fees
19 Oct - 20 Oct
Cozy Home in Pownal VT
A picnic table in a natural setting with a view of a hilly landscape.

4. 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 AU$215
includes taxes & fees
6 Oct - 7 Oct
Runamuk Farm Camp Tiny House near Cambridge, New York
A cabin with a sloped roof, large windows, and a balcony with outdoor seating.

5. 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, (24 reviews)
"Great cabin , so cozy with the wood burning stove "
United States
Susan f.
The price is AU$499
includes taxes & fees
12 Oct - 13 Oct
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
A snow-covered forest with a geodesic dome structure featuring a central fire.

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

Amanita Dome. All-inclusive food and drinks.
Cambridge
The price is AU$870
includes taxes & fees
21 Oct - 22 Oct
Amanita Dome. All-inclusive food and drinks.
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 AU$891
includes taxes & fees
7 Oct - 8 Oct
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A room with a large window, a wooden table, two chairs, and a woven basket on the table.

8. 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, (1 review)
"Beautiful place Very spacious and super organized we love our stay "
United States
Rafael
The price is AU$804
includes taxes & fees
20 Oct - 21 Oct
Cozy 3 Bedroom Condo in the Heart of Manchester VT
A room with a blue sofa, a wooden table, a chair, and a window with curtains.

9. Home on Hudson4 bedroom

Home on Hudson4 bedroom
Stillwater
The price is AU$681
includes taxes & fees
7 Oct - 8 Oct
Home on Hudson4 bedroom
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

10. 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 AU$368
includes taxes & fees
7 Oct - 8 Oct
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to 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 AU$793
includes taxes & fees
26 Oct - 27 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.

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 AU$669
includes taxes & fees
6 Oct - 7 Oct
Greylock Cabin
An outdoor dining area with tables and umbrellas, a wooden fence, and a building with large windows and lights.

13. 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 AU$722
includes taxes & fees
7 Oct - 8 Oct
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
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.

14. 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 AU$677
includes taxes & fees
6 Oct - 7 Oct
Modern Mount Snow Gnarvana - Steps to Carinthia
A kitchen with white cabinets, a wooden dining table, and pendant lights.

15. 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 AU$680
includes taxes & fees
13 Oct - 14 Oct
A roomy remodeled retreat close to MassMoCA
A wooden staircase leading to a cabin with a balcony, surrounded by trees.

16. New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly

New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly
Wilmington
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful house and a terrific central location for all things outdoors."
United States
Alex B.
The price is AU$1,111
includes taxes & fees
9 Oct - 10 Oct
New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly
A modern kitchen with a built-in fireplace, wine storage, and a dining area with wooden furniture.

17. 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, (13 reviews)
"great location easy access to the mountain and the pool was outstanding."
United States
jim f.
The price is AU$1,620
includes taxes & fees
6 Oct - 7 Oct
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

18. 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, (41 reviews)
"Our family had a wonderful vacation. The house and location were great. We will come back."
United States
Victoria L.
The price is AU$932
includes taxes & fees
20 Oct - 21 Oct
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A spacious kitchen with a central island, stainless steel appliances, and pendant lighting.

19. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is AU$1,156
includes taxes & fees
21 Oct - 22 Oct
1812 House, 2 Stays, 1 home
A large estate with a swimming pool, tennis court, and a spacious lawn.

20. The Privacy of a home & Perks of a Resort! Pool, Tennis, Views, Dogs, 6 baths!

The Privacy of a home & Perks of a Resort! Pool, Tennis, Views, Dogs, 6 baths!
Manchester
9.6 out of 10, Exceptional, (7 reviews)
"Great proximity to Bromley and Stratton, with easy access to plenty of restaurants in Manchester."
United States
Jessica G.
The price is AU$3,018
includes taxes & fees
21 Oct - 22 Oct
The Privacy of a home & Perks of a Resort! Pool, Tennis, Views, Dogs, 6 baths!
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 Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"Great place to stay"
Joseph 1-night trip
Posted 1 hour ago
The Black Bear Lodge at Stratton Mountain Resort

Find out more about North Bennington

North Bennington Holiday Homes information

Number of reviews
305
Accommodation
503 Holiday Homes
Lowest Price
AU$215
Highest Price
AU$3,018