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

Bennington Vacation Rentals

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Our top choices for Bennington vacation homes

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 CA $164
CA $408 total
includes taxes & fees
Nov 15 - Nov 16
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

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 CA $172
CA $747 total
includes taxes & fees
Nov 17 - Nov 18
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

3. 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 CA $166
CA $277 total
includes taxes & fees
Nov 15 - Nov 16
Cozy Home in Pownal VT

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

West Barn Suite at Hubbell Homestead - Mountain Views & Jetted Tub
Bennington
The price is CA $321
CA $391 total
includes taxes & fees
Nov 14 - Nov 15
West Barn Suite at Hubbell Homestead - Mountain Views & Jetted Tub

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 CA $449
CA $839 total
includes taxes & fees
Nov 15 - Nov 16
Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown

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 CA $120
CA $377 total
includes taxes & fees
Nov 16 - Nov 17
Long Trail House 368 condo in Stratton Village, walk to the lifts

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 CA $385
CA $821 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $514
CA $729 total
includes taxes & fees
Nov 15 - Nov 16
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 CA $642
CA $757 total
includes taxes & fees
Nov 29 - Nov 30
Wonderful hilltop house with breathtaking views

10. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is CA $426
CA $1,046 total
includes taxes & fees
Dec 1 - Dec 2
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 CA $408
CA $1,061 total
includes taxes & fees
Nov 17 - Nov 18
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 CA $308
CA $1,028 total
includes taxes & fees
Nov 15 - Nov 16
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 CA $539
CA $1,004 total
includes taxes & fees
Nov 20 - Nov 21
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 CA $321
CA $391 total
includes taxes & fees
Nov 14 - Nov 15
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, (119 reviews)
"enjoyed our week at this property"
United States
cory p.
The price is CA $268
CA $538 total
includes taxes & fees
Nov 14 - Nov 15
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

16. 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 CA $385
CA $779 total
includes taxes & fees
Nov 29 - Nov 30
Walk to Williams * Steam Sauna * Ritz-Carlton Bed

17. 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 CA $143
CA $167 total
includes taxes & fees
Nov 24 - Nov 25
The Eagles Wing at The CHM - Private Apartment

18. Amanita Dome. Inclusive Brunch & Dinner Experience

Amanita Dome. Inclusive Brunch & Dinner Experience
Cambridge
The price is CA $428
CA $851 total
includes taxes & fees
Nov 30 - Dec 1
Amanita Dome. Inclusive Brunch & Dinner Experience

19. 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 CA $292
CA $526 total
includes taxes & fees
Nov 14 - Nov 15
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views

20. 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 CA $280
CA $736 total
includes taxes & fees
Nov 16 - Nov 17
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
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 Vacation Homes information

Number of reviews
223
Accommodation
244 Vacation Homes
Lowest Price
CA $167
Highest Price
CA $1,061

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