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 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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, (10 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 $166
CA $294 total
includes taxes & fees
Oct 19 - Oct 20
Cozy Home in Pownal VT
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 CA $228
CA $510 total
includes taxes & fees
Oct 13 - Oct 14
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 CA $234
CA $633 total
includes taxes & fees
Oct 20 - Oct 21
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.

4. 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 $106
CA $368 total
includes taxes & fees
Oct 13 - Oct 14
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A room with a large window, a wooden table, two chairs, and a woven basket on the table.

5. 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, (2 reviews)
"Beautiful place Very spacious and super organized we love our stay "
United States
Rafael
The price is CA $308
CA $780 total
includes taxes & fees
Oct 14 - Oct 15
Cozy 3 Bedroom Condo in the Heart of Manchester VT
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

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, (43 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 $281
CA $945 total
includes taxes & fees
Oct 13 - Oct 14
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.

7. 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 $513
CA $773 total
includes taxes & fees
Oct 18 - Oct 19
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.

8. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is CA $423
CA $1,082 total
includes taxes & fees
Nov 3 - Nov 4
1812 House, 2 Stays, 1 home
A modern two-story house with a front porch, a staircase, and a driveway.

9. 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 $265
CA $1,220 total
includes taxes & fees
Oct 19 - Oct 20
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

10. 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 $485
CA $1,208 total
includes taxes & fees
Oct 28 - Oct 29
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
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 $539
CA $1,065 total
includes taxes & fees
Oct 19 - Oct 20
Cozy farmhouse in Manchester - short drive to multiple ski mountains!
A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.

12. 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, (116 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 $268
CA $567 total
includes taxes & fees
Oct 20 - Oct 21
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Property grounds

13. 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 $179
CA $210 total
includes taxes & fees
Oct 13 - Oct 14
Runamuk Farm Camp Tiny House near Cambridge, New York
A cabin with a sloped roof, large windows, and a balcony with outdoor seating.

14. 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 $255
CA $500 total
includes taxes & fees
Oct 13 - Oct 14
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

15. 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 $433
CA $882 total
includes taxes & fees
Oct 13 - Oct 14
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
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 CA $171
CA $226 total
includes taxes & fees
Oct 15 - Oct 16
The Eagles Wing at The CHM - Private Apartment
A snow-covered forest with a geodesic dome structure featuring a central fire.

17. Amanita Dome. All-inclusive food and drinks.

Amanita Dome. All-inclusive food and drinks.
Cambridge
The price is CA $428
CA $893 total
includes taxes & fees
Oct 26 - Oct 27
Amanita Dome. All-inclusive food and drinks.
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

18. 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 $279
CA $809 total
includes taxes & fees
Oct 13 - Oct 14
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

19. Greylock Cabin

Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"This is a beautiful cabin on an amazing property with a great view of Mt Greylock! Clean, comfortable, great location, communication with the owner was outstanding and questions were answered quickly. It all went smoothly and we highly recommend this property!"
United States
Margaret M.
The price is CA $397
CA $657 total
includes taxes & fees
Nov 8 - Nov 9
Greylock Cabin
A spacious living room with wooden floors, a high ceiling with exposed beams, a dining area with a table and chairs, and large windows offering a view of the outdoors.

20. Killington Retreat | Deck-Fire Pit-Mountain Views!

Killington Retreat | Deck-Fire Pit-Mountain Views!
Clarendon
9.2 out of 10, Wonderful, (5 reviews)
"Beautiful house! It had everything we needed for a fun and relaxing week. "
United States
Joshua
The price is CA $179
CA $569 total
includes taxes & fees
Oct 24 - Oct 25
Killington Retreat | Deck-Fire Pit-Mountain Views!
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

8/10 Good
"This hotel was in a great location right next to a grocery store and a Chili's restaurant. Also only 10 minutes from the historic downtown. The woman at the front desk was so kind and sweet, she made me feel very welcome! The only issue I had with the room is that there was no microwave, which surprised me. But all in all, it was a great stay!"
Sherri 1-night trip
Posted 6 hours ago
Hampton Inn Bennington

Find out more about Bennington

Bennington Vacation Homes information

Number of reviews
253
Accommodation
244 Vacation Homes
Lowest Price
CA $210
Highest Price
CA $1,208

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