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. 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 $137
CA $340 total
includes taxes & fees
Aug 31 - Sep 1
Peaceful getaway at birds of a feather

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 $192
CA $568 total
includes taxes & fees
Sep 13 - Sep 14
Two Brooks Lodge

3. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (6 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 $160
CA $280 total
includes taxes & fees
Aug 31 - Sep 1
Cozy Home in Pownal VT

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, (35 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 $199
CA $466 total
includes taxes & fees
Sep 13 - Sep 14
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

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 $355 total
includes taxes & fees
Aug 23 - Aug 24
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

6. 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 $287
CA $1,242 total
includes taxes & fees
Aug 26 - Aug 27
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

7. 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)
"House was clean and pet-friendly! Great location between Bromley and Stratton!"
United States
Michael I.
The price is CA $273
CA $916 total
includes taxes & fees
Aug 27 - Aug 28
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

8. Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Jamaica
9.2 out of 10, Wonderful, (27 reviews)
"We enjoyed our stay at a great ski house that was in a good location to the mountain. Accommodations were comfortable for 6 adults and 4 kids and the shuffleboard, foosball and pool tables were a hit. "
United States
Jonathan H.
The price is CA $261
CA $1,190 total
includes taxes & fees
Aug 26 - Aug 27
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

9. 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, (13 reviews)
"Clean, lots of room, easy access to Stratton, responsive host."
United States
Mark H.
The price is CA $428
CA $1,133 total
includes taxes & fees
Aug 25 - Aug 26
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

10. 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 $497
CA $741 total
includes taxes & fees
Sep 2 - Sep 3
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.

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 $522
CA $1,031 total
includes taxes & fees
Aug 27 - Aug 28
Cozy farmhouse in Manchester - short drive to multiple ski mountains!

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 $732
CA $1,976 total
includes taxes & fees
Aug 26 - Aug 27
Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.

13. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is CA $427
CA $1,087 total
includes taxes & fees
Sep 13 - Sep 14
1812 House, 2 Stays, 1 home

14. 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, (111 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 $289
CA $582 total
includes taxes & fees
Sep 8 - Sep 9
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

15. 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 $167
CA $198 total
includes taxes & fees
Aug 24 - Aug 25
Runamuk Farm Camp Tiny House near Cambridge, New York

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 $224
CA $424 total
includes taxes & fees
Aug 31 - Sep 1
Charming 3-bedroom Vermont house with outdoor Sauna and 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, (23 reviews)
"Great cabin , so cozy with the wood burning stove "
United States
Susan f.
The price is CA $247
CA $488 total
includes taxes & fees
Aug 24 - Aug 25
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views

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 $316
CA $607 total
includes taxes & fees
Sep 9 - Sep 10
A roomy remodeled retreat close to MassMoCA

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, (19 reviews)
"Great place!"
United States
Jack & Heather G.
The price is CA $272
CA $792 total
includes taxes & fees
Sep 16 - Sep 17
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

20. Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Whitingham
10.0 out of 10, Exceptional, (15 reviews)
"Great 2 family group vacation spot. Very clean and right in between great ski mountains"
United States
Jonathan
The price is CA $287
CA $716 total
includes taxes & fees
Sep 2 - Sep 3
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
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
385
Accommodation
255 Vacation Homes
Lowest Price
CA $198
Highest Price
CA $1,976

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