A covered bridge with a sign reading "Silk Road Bridge" and a height restriction of 10 feet 6 inches.

Holiday Homes in Bennington

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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 Bennington holiday homes

A two-story house with a porch, surrounded by trees and snow.

1. 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 €260
includes taxes & fees
1 Nov - 2 Nov
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
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 €480
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.

3. 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 €189
includes taxes & fees
1 Nov - 2 Nov
Cozy Home in Pownal VT
Exterior

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

East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub
Bennington
East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub
A snow-covered landscape with a cabin surrounded by trees.

5. 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 €535
includes taxes & fees
2 Nov - 3 Nov
Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

6. 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 €236
includes taxes & fees
2 Nov - 3 Nov
Long Trail House 368 condo in Stratton Village, walk to the lifts
A room with a large window, a wooden table, two chairs, and a woven basket on the table.

7. 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 €557
includes taxes & fees
1 Nov - 2 Nov
Cozy 3 Bedroom Condo in the Heart of Manchester VT
An outdoor dining area with tables and umbrellas, a wooden fence, and a building with large windows and lights.

8. 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 €523
includes taxes & fees
13 Nov - 14 Nov
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

9. Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Winhall
10.0 out of 10, Exceptional, (15 reviews)
"Clean, lots of room, easy access to Stratton, responsive host."
United States
Mark H.
The price is €697
includes taxes & fees
1 Nov - 2 Nov
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A spacious kitchen with a central island, stainless steel appliances, and pendant lighting.

10. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is €634
includes taxes & fees
3 Nov - 4 Nov
1812 House, 2 Stays, 1 home
A rustic interior with a wooden ceiling, a bar area with stools, a sofa, and a dining table.

11. Wonderful hilltop house with breathtaking views

Wonderful hilltop house with breathtaking views
Dorset
The price is €696
includes taxes & fees
13 Nov - 14 Nov
Wonderful hilltop house with breathtaking views
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

12. 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 €645
includes taxes & fees
1 Nov - 2 Nov
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A two-story white house with a front porch, a door with a wreath, and a chimney.

13. Cozy farmhouse in Manchester - short drive to multiple ski mountains!

Cozy farmhouse in Manchester - short drive to multiple ski mountains!
Manchester
9.4 out of 10, Exceptional, (3 reviews)
"The hosts were very friendly and responsive during our stay. Loved that the house is close to the main town as well as close to the ski slopes (Bromley). "
United States
Marissa H.
The price is €664
includes taxes & fees
13 Nov - 14 Nov
Cozy farmhouse in Manchester - short drive to multiple ski mountains!
A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.

14. 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 €355
includes taxes & fees
13 Nov - 14 Nov
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
A cabin with a sloped roof, large windows, and a balcony with outdoor seating.

15. 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 €346
includes taxes & fees
13 Nov - 14 Nov
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.

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

Amanita Dome. All-inclusive food and drinks.
Cambridge
The price is €530
includes taxes & fees
1 Dec - 2 Dec
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.

17. 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 €542
includes taxes & fees
22 Nov - 23 Nov
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

18. 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 €486
includes taxes & fees
1 Nov - 2 Nov
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A kitchen with white cabinets, a wooden dining table, and pendant lights.

19. 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 €424
includes taxes & fees
1 Nov - 2 Nov
A roomy remodeled retreat close to MassMoCA
A log cabin with a balcony, surrounded by snow-covered trees and a wind turbine in the background.

20. 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 €405
includes taxes & fees
1 Nov - 2 Nov
Greylock Cabin
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 Bennington Hotel Reviews

Bennington Motor Inn

Bennington Motor Inn

8/10 Good
"I had reserved a room in this motel online and we arrived to see adults and children hanging out in front, indicating that it was home for them. Checking in was awkward, as the clerk had to call the owner or manager to check k that we had a reservation. We were wary about staying because of the noise level but were given a room in the back of the hotel and were delighted to find the room was quiet, immaculate, had all the amenities, and was very nicely decorated. The beds were very comfortable and we would stay there again in this part of the motel."
Hilary 1-night trip
Posted 4 hours ago
Bennington Motor Inn

Find out more about Bennington

Bennington Holiday Homes information

Number of reviews
405
Accommodation
257 Holiday Homes
Lowest Price
€189
Highest Price
€697