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Our top choices for North Bennington holiday homes
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"
cory p.
The price is €340
includes taxes & fees
15 Nov - 16 Nov
2. Red Country Escape with Mountain Views
Red Country Escape with Mountain ViewsEagle 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."
Susan M.
The price is €303
includes taxes & fees
15 Nov - 16 Nov
3. West Barn Suite at Hubbell Homestead - Mountain Views & Jetted Tub
West Barn Suite at Hubbell Homestead - Mountain Views & Jetted TubBennington
The price is €251
includes taxes & fees
15 Dec - 16 Dec
4. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT RetreatBennington
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."
Malika R.
The price is €264
includes taxes & fees
16 Nov - 17 Nov
5. East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub
East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted TubBennington
The price is €251
includes taxes & fees
11 Dec - 12 Dec
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, VermontWoodford
10.0 out of 10, Exceptional, (1 review)
"Enjoyed our stay! Very clean and comfortable."
Dana W.
The price is €477
includes taxes & fees
16 Nov - 17 Nov
7. Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible viewsshushan
9.6 out of 10, Exceptional, (27 reviews)
"Great cabin , so cozy with the wood burning stove "
Susan f.
The price is €331
includes taxes & fees
15 Nov - 16 Nov
8. Cozy Home in Pownal VT
Cozy Home in Pownal VTPownal
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."
Jeri R.
The price is €181
includes taxes & fees
15 Nov - 16 Nov
9. Amanita Dome. Inclusive Brunch & Dinner Experience
Amanita Dome. Inclusive Brunch & Dinner ExperienceCambridge
The price is €535
includes taxes & fees
13 Dec - 14 Dec
10. Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown
Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to WilliamstownPownal
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."
Claudette R.
The price is €544
includes taxes & fees
19 Nov - 20 Nov
11. Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Walk to Williams * Steam Sauna * Ritz-Carlton BedWilliamstown
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. "
Michelle B.
The price is €495
includes taxes & fees
30 Nov - 1 Dec
12. Long Trail House 368 condo in Stratton Village, walk to the lifts
Long Trail House 368 condo in Stratton Village, walk to the liftsStratton
The price is €243
includes taxes & fees
21 Nov - 22 Nov
13. Modern Mount Snow Gnarvana - Steps to Carinthia
Modern Mount Snow Gnarvana - Steps to CarinthiaDover
10.0 out of 10, Exceptional, (26 reviews)
"Perfect for our getaway, convenient for getting to the slopes and a beautiful area to visit"
Lynn B.
The price is €584
includes taxes & fees
10 Dec - 11 Dec
14. Home on Hudson4 bedroom
Home on Hudson4 bedroomStillwater
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!"
Dina F.
The price is €411
includes taxes & fees
15 Nov - 16 Nov
15. Greylock Cabin
Greylock CabinFlorida
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!"
Margaret M.
The price is €427
includes taxes & fees
13 Dec - 14 Dec
16. A roomy remodeled retreat close to MassMoCA
A roomy remodeled retreat close to MassMoCANorth 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."
Diane
The price is €442
includes taxes & fees
4 Dec - 5 Dec
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)."
Natalie
The price is €470
includes taxes & fees
16 Nov - 17 Nov
18. Cozy 3 Bedroom Condo in the Heart of Manchester VT
Cozy 3 Bedroom Condo in the Heart of Manchester VTManchester
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful accommodations. Great communication with host."
Peggy S.
The price is €533
includes taxes & fees
15 Nov - 16 Nov
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."
jim f.
The price is €938
includes taxes & fees
15 Nov - 16 Nov
20. 1812 House, 2 Stays, 1 home
1812 House, 2 Stays, 1 homeManchester
The price is €669
includes taxes & fees
1 Dec - 2 Dec
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.
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.
Photo by Laury Kelly
Open Photo by Laury Kelly
Top reviews in North Bennington
New Englander Inn Bennington
New Englander Inn BenningtonBennington
10/10 Excellent
Excellent small hotel with swimming pool. Best option in town. Staff polite and friendly here. I made the mistake of asking help at nearby Knotty Pines hotel, where manager was not very helpful!
Frank
