A house on a grassy hill surrounded by autumn-colored trees.

Vacation Rentals in Bennington County

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Our top choices for Bennington County vacation rentals

A two-story blue house with a porch, surrounded by a garden with orange flowers.

1. Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
9.8 out of 10, Exceptional, (36 reviews)
"Perfect for our weekend getaway. Close to the activities we wanted in North Adams, Mass, but just across the state line in a lovely rural setting. A very nice apartment... just as described. So happy to have chosen this for our stay!"
United States
Bill
The price is ￥12,093
￥24,169 total
includes taxes & fees
Oct 19 - Oct 20
Getaway Near Mass MoCA, Great Hiking, Scenic Views
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

2. 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 ￥18,353
￥32,417 total
includes taxes & fees
Oct 29 - Oct 30
Cozy Home in Pownal VT
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
10.0 out of 10, Exceptional, (1 review)
"Enjoyed our stay! Very clean and comfortable."
United States
Dana W.
The price is ￥23,222
￥66,366 total
includes taxes & fees
Oct 19 - Oct 20
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A two-story house with a porch, surrounded by trees and snow.

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 ￥24,664
￥56,050 total
includes taxes & fees
Oct 20 - Oct 21
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
A white building with green shutters, a covered porch, and a landscaped garden with flowers.

5. ADA King Room w/ Roll-In Shower & Views

ADA King Room w/ Roll-In Shower & Views
Manchester Village Historic District
The price is ￥32,561
￥39,390 total
includes taxes & fees
Nov 4 - Nov 5
ADA King Room w/ Roll-In Shower & Views
A dining room with a wooden table, four chairs, a vase with flowers, and a view of greenery outside.

6. Historic Home with Colonial Charm in Manchester

Historic Home with Colonial Charm in Manchester
Manchester
10.0 out of 10, Exceptional, (2 reviews)
"The accommodations were absolutely amazing. We had a wonderful time. The home is beautiful. The host is very communicative."
United States
Victor G.
The price is ￥17,750
￥62,935 total
includes taxes & fees
Nov 3 - Nov 4
Historic Home with Colonial Charm in Manchester
A playground with slides and climbing structures surrounded by trees.

7. Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (21 reviews)
"Nice place "
United States
Janja L.
The price is ￥20,353
￥59,471 total
includes taxes & fees
Nov 2 - Nov 3
Cozy Bromley Retreat
A modern kitchen with a central island, stainless steel appliances, pendant lighting, and a view to the dining area.

8. Modern Mountain Retreat w/ Chef’s Kitchen

Modern Mountain Retreat w/ Chef’s Kitchen
Manchester
10.0 out of 10, Exceptional, (1 review)
"Communication with Caroline was top notch and speedy! Very clear instructions for accessing the property and check out. Even though this place is connected with two other rooms/units ( I think that is what it is) we never heard them and hopefully we didn't bother them either!The house was amazing inside and out. The location was exceptional!Thank you for a beautiful stay!"
United States
Eva G.
The price is ￥23,609
￥70,448 total
includes taxes & fees
Nov 3 - Nov 4
Modern Mountain Retreat w/ Chef’s Kitchen
Property grounds

9. Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (66 reviews)
"Excellent place, fantastic hosts, highly recommend."
United States
Mike K.
The price is ￥30,592
￥42,941 total
includes taxes & fees
Oct 19 - Oct 20
Spacious apartment in beautiful, historic Arlington VT
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

10. 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 ￥31,201
￥104,823 total
includes taxes & fees
Oct 19 - Oct 20
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A room with a large window, a wooden table, two chairs, and a woven basket on the table.

11. 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 ￥42,682
￥97,359 total
includes taxes & fees
Oct 20 - Oct 21
Cozy 3 Bedroom Condo in the Heart of Manchester VT
A large indoor swimming pool with wooden beams and a central decorative structure.

12. Equinox Getaway | Queen Guest Room w/ Sauna & Spa

Equinox Getaway | Queen Guest Room w/ Sauna & Spa
Manchester Village Historic District
The price is ￥30,123
￥37,601 total
includes taxes & fees
Nov 4 - Nov 5
Equinox Getaway | Queen Guest Room w/ Sauna & Spa
An outdoor dining area with a wooden deck, a table set with plates, glasses, and a vase of flowers.

13. Tranquil Brookside Retreat with Hot Tub & Firepit

Tranquil Brookside Retreat with Hot Tub & Firepit
Peru
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful place. Comfortable and well furnished. "
United States
Michael B.
The price is ￥38,513
￥110,014 total
includes taxes & fees
Nov 1 - Nov 2
Tranquil Brookside Retreat with Hot Tub & Firepit
Terrace/patio

14. The Birchwood Cabin - Stunning Mountain Views

The Birchwood Cabin - Stunning Mountain Views
Sunderland
10.0 out of 10, Exceptional, (4 reviews)
"Excellent host very responsive. Beautiful cozy cabin with all the amenities you need. Highly recommend! "
United States
Robert V.
The price is ￥38,589
￥103,247 total
includes taxes & fees
Oct 28 - Oct 29
The Birchwood Cabin - Stunning Mountain Views
A large indoor swimming pool with wooden beams and a central decorative structure.

15. Cupola Suite w/ Mountain View + Spa Access

Cupola Suite w/ Mountain View + Spa Access
Manchester Village Historic District
The price is ￥51,066
￥63,676 total
includes taxes & fees
Nov 11 - Nov 12
Cupola Suite w/ Mountain View + Spa Access
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

16. 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 ￥52,173
￥128,273 total
includes taxes & fees
Oct 19 - Oct 20
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A spacious kitchen with a central island, stainless steel appliances, and pendant lighting.

17. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is ￥44,283
￥118,456 total
includes taxes & fees
Nov 3 - Nov 4
1812 House, 2 Stays, 1 home
An outdoor dining area with tables and umbrellas, a wooden fence, and a building with large windows and lights.

18. 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 ￥56,909
￥84,671 total
includes taxes & fees
Oct 18 - Oct 19
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
A modern living room with a fireplace, a large sofa set, and a view through the glass doors.

19. New! Vermont Getaway! Stratton - close to skiing!

New! Vermont Getaway! Stratton - close to skiing!
Winhall
10.0 out of 10, Exceptional, (1 review)
"The place was perfect for us! Easy stay. Very clean and the wood burning fireplace was great. Would def recommend!"
United States
Carolyn K.
The price is ￥63,232
￥101,056 total
includes taxes & fees
Nov 1 - Nov 2
New! Vermont Getaway! Stratton - close to skiing!
A room with a wooden coffee table, two white chairs, and a carpeted floor.

20. Mountain Retreat with Outdoor Living Space and Ping Pong Table in Vermont

Mountain Retreat with Outdoor Living Space and Ping Pong Table in Vermont
Winhall
10.0 out of 10, Exceptional, (1 review)
"Sierra was great to work with upon check in. We really enjoyed our stay."
United States
Jonathan W. B.
The price is ￥70,111
￥90,481 total
includes taxes & fees
Oct 21 - Oct 22
Mountain Retreat with Outdoor Living Space and Ping Pong Table in Vermont
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 County Hotel Reviews

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Very nice hotel! Recommend"
Vladimir 1-night trip
Posted 14 hours ago
Hampton Inn and Suites Manchester

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Vacation Apartments in Bennington County

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