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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Our top choices for Bennington holiday homes

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

West Barn Suite at Hubbell Homestead - Mountain Views & Jetted Tub
Bennington
The price is AU$397
includes taxes & fees
15 Nov - 16 Nov
West Barn Suite at Hubbell Homestead - Mountain Views & Jetted Tub

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$414
includes taxes & fees
15 Nov - 16 Nov
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

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
10.0 out of 10, Exceptional, (1 review)
"Enjoyed our stay! Very clean and comfortable."
United States
Dana W.
The price is AU$760
includes taxes & fees
16 Nov - 17 Nov
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

4. 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 AU$292
includes taxes & fees
23 Nov - 24 Nov
Cozy Home in Pownal VT

5. 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 AU$384
includes taxes & fees
16 Nov - 17 Nov
Long Trail House 368 condo in Stratton Village, walk to the lifts

6. 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 AU$839
includes taxes & fees
20 Nov - 21 Nov
Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown

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 AU$855
includes taxes & fees
15 Nov - 16 Nov
Cozy 3 Bedroom Condo in the Heart of Manchester VT

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)
"Very clean and convenient to the town and very helpful host!"
United States
Corry B.
The price is AU$742
includes taxes & fees
15 Nov - 16 Nov
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.

9. Wonderful hilltop house with breathtaking views

Wonderful hilltop house with breathtaking views
Dorset
The price is AU$771
includes taxes & fees
29 Nov - 30 Nov
Wonderful hilltop house with breathtaking views

10. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is AU$1,055
includes taxes & fees
1 Dec - 2 Dec
1812 House, 2 Stays, 1 home

11. 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$1,068
includes taxes & fees
16 Nov - 17 Nov
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

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, (45 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$1,067
includes taxes & fees
15 Nov - 16 Nov
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

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 AU$1,025
includes taxes & fees
23 Nov - 24 Nov
Cozy farmhouse in Manchester - short drive to multiple ski mountains!

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

East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub
Bennington
The price is AU$397
includes taxes & fees
15 Nov - 16 Nov
East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub

15. 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 AU$544
includes taxes & fees
15 Nov - 16 Nov
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

16. 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 AU$489
includes taxes & fees
15 Nov - 16 Nov
Red Country Escape with Mountain Views

17. 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 AU$517
includes taxes & fees
20 Nov - 21 Nov
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views

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$786
includes taxes & fees
29 Nov - 30 Nov
Walk to Williams * Steam Sauna * Ritz-Carlton Bed

19. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.8 out of 10, Exceptional, (7 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is AU$188
includes taxes & fees
19 Nov - 20 Nov
The Eagles Wing at The CHM - Private Apartment

20. Amanita Dome. Inclusive Brunch & Dinner Experience

Amanita Dome. Inclusive Brunch & Dinner Experience
Cambridge
The price is AU$863
includes taxes & fees
24 Nov - 25 Nov
Amanita Dome. Inclusive Brunch & Dinner Experience
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

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Bennington Holiday Homes information

Number of reviews
211
Accommodation
253 Holiday Homes
Lowest Price
AU$188
Highest Price
AU$1,068