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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Bennington holiday homes

A red house with a porch, surrounded by a grassy yard and trees.

1. Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3 reviews)
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
The price is AU$568
includes taxes & fees
1 Oct - 2 Oct
Two Brooks Lodge
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 AU$459
includes taxes & fees
1 Oct - 2 Oct
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
A bedroom with a bed, bedside tables, a window, and a radiator.

3. 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$641
includes taxes & fees
7 Oct - 8 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.

4. 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$295
includes taxes & fees
8 Oct - 9 Oct
Cozy Home in Pownal VT
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

5. 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$367
includes taxes & fees
1 Oct - 2 Oct
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A spacious kitchen with a large island, a stone fireplace, and wooden beams.

6. Views for Days | Hot Tub, Sauna, EV, A/C | 6 Min to Stratton, 15 to Bromley

Views for Days | Hot Tub, Sauna, EV, A/C | 6 Min to Stratton, 15 to Bromley
Winhall
10.0 out of 10, Exceptional, (13 reviews)
"House was great for our family ski trip! "
United States
Brooke S.
The price is AU$944
includes taxes & fees
1 Oct - 2 Oct
Views for Days | Hot Tub, Sauna, EV, A/C | 6 Min to Stratton, 15 to Bromley
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

7. 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 AU$1,328
includes taxes & fees
19 Oct - 20 Oct
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A spacious kitchen with a central island, stainless steel appliances, and pendant lighting.

8. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
1812 House, 2 Stays, 1 home
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

9. 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$928
includes taxes & fees
20 Oct - 21 Oct
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
An outdoor dining area with tables and umbrellas, a wooden fence, and a building with large windows and lights.

10. 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$719
includes taxes & fees
7 Oct - 8 Oct
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
A two-story white house with a front porch, a door with a wreath, and a chimney.

11. 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 AU$1,044
includes taxes & fees
8 Oct - 9 Oct
Cozy farmhouse in Manchester - short drive to multiple ski mountains!
A large estate with a swimming pool, tennis court, and a spacious lawn.

12. 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$2,987
includes taxes & fees
21 Oct - 22 Oct
The Privacy of a home & Perks of a Resort! Pool, Tennis, Views, Dogs, 6 baths!
A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.

13. 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$553
includes taxes & fees
1 Oct - 2 Oct
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
A picnic table in a natural setting with a view of a hilly landscape.

14. 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$214
includes taxes & fees
5 Oct - 6 Oct
Runamuk Farm Camp Tiny House near Cambridge, New York
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, (24 reviews)
"Great cabin , so cozy with the wood burning stove "
United States
Susan f.
The price is AU$488
includes taxes & fees
13 Oct - 14 Oct
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
A bedroom with a large bed, a window with blinds, a bookshelf, and a wall-mounted ship's wheel.

16. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.6 out of 10, Exceptional, (5 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is AU$212
includes taxes & fees
6 Oct - 7 Oct
The Eagles Wing at The CHM - Private Apartment
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.

17. 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$665
includes taxes & fees
1 Oct - 2 Oct
Modern Mount Snow Gnarvana - Steps to Carinthia
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

18. 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$887
includes taxes & fees
1 Oct - 2 Oct
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

19. 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$811
includes taxes & fees
6 Oct - 7 Oct
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.

20. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (60 reviews)
"Lovely home with everything we needed. The beds were very comfortable!"
United States
Jennifer O.
The price is AU$677
includes taxes & fees
13 Oct - 14 Oct
A roomy remodeled retreat close to MassMoCA
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

Knotty Pine

Knotty Pine

10/10 Excellent
"We had a nice stay at the Knotty Pine Motel. The room was clean, spacious, and comfortable, and check-in was quick and easy. Overall, everything was well kept and made for a pleasant stay. The only downside for me was that the bed was a bit harder than I prefer, but that’s a personal preference. Overall, a good place to stay, definitely would stay there again."
Scott 2-night trip
Posted 16 hours ago
Knotty Pine

Find out more about Bennington

Bennington Holiday Homes information

Number of reviews
351
Accommodation
253 Holiday Homes
Lowest Price
AU$214
Highest Price
AU$2,987