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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Check prices for these dates

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

Our top choices for Bennington vacation homes

A wooden kitchen with a central island, bar stools, and a dining table with chairs.

1. 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 CA $164
CA $290 total
includes taxes & fees
Oct 8 - Oct 9
Cozy Home in Pownal VT
A red house with a porch, surrounded by a grassy yard and trees.

2. 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 CA $160
CA $543 total
includes taxes & fees
Sep 29 - Sep 30
Two Brooks Lodge
A two-story house with a porch, surrounded by trees and snow.

3. 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 $170
CA $435 total
includes taxes & fees
Sep 29 - Sep 30
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
A bedroom with a bed, bedside tables, a window, and a radiator.

4. 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 CA $220
CA $612 total
includes taxes & fees
Sep 29 - Sep 30
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
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 CA $105
CA $364 total
includes taxes & fees
Oct 1 - Oct 2
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 CA $379
CA $978 total
includes taxes & fees
Oct 1 - Oct 2
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 CA $467
CA $1,181 total
includes taxes & fees
Sep 29 - Sep 30
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

8. 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 CA $279
CA $938 total
includes taxes & fees
Oct 19 - Oct 20
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.

9. 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 CA $477
CA $726 total
includes taxes & fees
Sep 29 - Sep 30
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
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 CA $410
CA $1,077 total
includes taxes & fees
Sep 29 - Sep 30
1812 House, 2 Stays, 1 home
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 CA $535
CA $1,056 total
includes taxes & fees
Oct 4 - Oct 5
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 CA $1,909
CA $3,064 total
includes taxes & fees
Oct 21 - Oct 22
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 CA $266
CA $562 total
includes taxes & fees
Sep 29 - Sep 30
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
A small cabin with a wooden deck, a front door, and large windows.

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 CA $177
CA $209 total
includes taxes & fees
Sep 29 - Sep 30
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 CA $253
CA $499 total
includes taxes & fees
Sep 29 - Sep 30
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
A deck with two wicker chairs and a string of lights against a backdrop of trees and a sunset.

16. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.6 out of 10, Exceptional, (4 reviews)
"Open modern clean space in a lovely quiet location. The hosts were very responsive and helpful. We would be happy to visit again."
United States
Matthew C.
The price is CA $147
CA $198 total
includes taxes & fees
Sep 29 - Sep 30
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 CA $191
CA $609 total
includes taxes & fees
Sep 30 - Oct 1
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 CA $430
CA $875 total
includes taxes & fees
Sep 29 - Sep 30
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, (20 reviews)
"Great place!"
United States
Jack & Heather G.
The price is CA $277
CA $806 total
includes taxes & fees
Oct 6 - Oct 7
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

Hampton Inn Bennington

Hampton Inn Bennington

10/10 Excellent
"Mighty fine"
Jerry 1-night trip
Posted 1 day ago
Hampton Inn Bennington

Find out more about Bennington

Bennington Vacation Homes information

Number of reviews
290
Accommodation
255 Vacation Homes
Lowest Price
CA $209
Highest Price
CA $3,064

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