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
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Bennington vacation homes

Exterior

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 CA $164
CA $539 total
includes taxes & fees
Sep 2 - Sep 3
Two Brooks Lodge
Interior

2. Peaceful getaway at birds of a feather

Peaceful getaway at birds of a feather
Shaftsbury
9.8 out of 10, Exceptional, (38 reviews)
"Great place"
United States
Aidan K.
The price is CA $155
CA $364 total
includes taxes & fees
Sep 2 - Sep 3
Peaceful getaway at birds of a feather
Dining

3. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (7 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 $148
CA $267 total
includes taxes & fees
Sep 13 - Sep 14
Cozy Home in Pownal VT
Exterior

4. 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 $179
CA $438 total
includes taxes & fees
Sep 13 - Sep 14
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Interior

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 $103
CA $356 total
includes taxes & fees
Sep 9 - Sep 10
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Outdoor spa tub

6. 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, (40 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 $273
CA $919 total
includes taxes & fees
Sep 2 - Sep 3
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Exterior detail

7. Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Jamaica
9.6 out of 10, Exceptional, (30 reviews)
"House was perfect for a guys trip for skiing. Just as expected. Would stay again. "
United States
Michael A.
The price is CA $273
CA $1,220 total
includes taxes & fees
Sep 2 - Sep 3
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
TV, fireplace, books, music library

8. 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, (14 reviews)
"Clean, lots of room, easy access to Stratton, responsive host."
United States
Mark H.
The price is CA $416
CA $1,118 total
includes taxes & fees
Sep 15 - Sep 16
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Outdoor dining

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 $499
CA $748 total
includes taxes & fees
Sep 2 - Sep 3
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
Private kitchen

10. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is CA $424
CA $1,086 total
includes taxes & fees
Sep 13 - Sep 14
1812 House, 2 Stays, 1 home
Exterior

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 $524
CA $1,035 total
includes taxes & fees
Sep 8 - Sep 9
Cozy farmhouse in Manchester - short drive to multiple ski mountains!
Exterior

12. Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.

Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.
Stratton
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful stay! The location was extremely convenient to the mountain, and the house was clean, comfortable and spacious. We loved all of the seating in the living room, the large fireplace, and cozy hot tub."
United States
Steve M.
The price is CA $656
CA $1,875 total
includes taxes & fees
Sep 2 - Sep 3
Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.
Coffee/tea maker, fridge, microwave, oven

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, (113 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 $261
CA $545 total
includes taxes & fees
Sep 8 - Sep 9
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Exterior

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, (2 reviews)
"Phenomenal site, with stunning views. Highly recommend!"
United States
Jess M.
The price is CA $168
CA $198 total
includes taxes & fees
Sep 2 - Sep 3
Runamuk Farm Camp Tiny House near Cambridge, New York
Dining

15. 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, (19 reviews)
"Great place!"
United States
Jack & Heather G.
The price is CA $272
CA $790 total
includes taxes & fees
Sep 15 - Sep 16
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Property grounds

16. Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views

Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views
Stamford
9.8 out of 10, Exceptional, (7 reviews)
"Beautiful area and views of mountains, very gracious host "
United States
Donna E.
The price is CA $262
CA $470 total
includes taxes & fees
Sep 9 - Sep 10
Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views
Exterior

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, (23 reviews)
"Great cabin , so cozy with the wood burning stove "
United States
Susan f.
The price is CA $248
CA $489 total
includes taxes & fees
Sep 2 - Sep 3
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
Dining

18. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (58 reviews)
"Lovely home with everything we needed. The beds were very comfortable!"
United States
Jennifer O.
The price is CA $317
CA $667 total
includes taxes & fees
Sep 9 - Sep 10
A roomy remodeled retreat close to MassMoCA
In-room safe, iron/ironing board, WiFi, bed sheets

19. MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is CA $317
CA $961 total
includes taxes & fees
Sep 2 - Sep 3
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Exterior

20. North Getaway Cottage

North Getaway Cottage
Williamstown
8.8 out of 10, Excellent, (27 reviews)
"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"
United States
Carole S.
The price is CA $312
CA $661 total
includes taxes & fees
Sep 17 - Sep 18
North Getaway Cottage
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

8/10 Good
"Clean and convenient."
Terence 1-night trip
Posted 1 day ago
Knotty Pine

Find out more about Bennington

Bennington Vacation Homes information

Number of reviews
334
Accommodation
255 Vacation Homes
Lowest Price
CA $198
Highest Price
CA $1,875

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