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

Holiday Rentals in Bennington County

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Top Cities in Bennington County

A calm river with rocky formations and dense green trees in the background.
Holiday RentalsHoliday Rentals

Dorset

Dorset

Our top choices for Bennington County holiday 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
10.0 out of 10, Exceptional, (35 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 €138
includes taxes & fees
30 Sept - 1 Oct
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, (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 €175
includes taxes & fees
27 Sept - 28 Sept
Cozy Home in Pownal VT
A room with wooden walls, a window with a view of the sky and greenery, a hanging macrame wall decoration, and a vase with flowers on the windowsill.

3. Peaceful getaway at birds of a feather

Peaceful getaway at birds of a feather
Shaftsbury
9.8 out of 10, Exceptional, (38 reviews)
"Laurie was an amazing host, with an amazing property! What an adorable home with an adorable view."
United States
Michaela J.
Peaceful getaway at birds of a feather
A red house with a porch, surrounded by a grassy yard and trees.

4. 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 €361
includes taxes & fees
29 Sept - 30 Sept
Two Brooks Lodge
A two-story house with a porch, surrounded by trees and snow.

5. 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 €306
includes taxes & fees
29 Sept - 30 Sept
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
A playground with slides and climbing structures surrounded by trees.

6. Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (20 reviews)
"Nice place "
United States
Janja L.
The price is €342
includes taxes & fees
30 Sept - 1 Oct
Cozy Bromley Retreat
A two-story house with a red roof, a front porch with a railing, and a gravel driveway.

7. 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 €400
includes taxes & fees
28 Sept - 29 Sept
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
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 €633
includes taxes & fees
25 Oct - 26 Oct
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9. Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (65 reviews)
"Excellent place, fantastic hosts, highly recommend."
United States
Mike K.
The price is €251
includes taxes & fees
25 Oct - 26 Oct
Spacious apartment in beautiful, historic Arlington VT
A dining room with a wooden table, four chairs, a vase with flowers, and a view of greenery outside.

10. 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 €406
includes taxes & fees
21 Oct - 22 Oct
Historic Home with Colonial Charm in Manchester
A modern kitchen with a central island, stainless steel appliances, pendant lighting, and a view to the dining area.

11. 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 €504
includes taxes & fees
21 Oct - 22 Oct
Modern Mountain Retreat w/ Chef’s Kitchen
A cabin with a triangular roof, a wooden deck, and a front porch.

12. The Vermont A-Frame Mountain Retreat

The Vermont A-Frame Mountain Retreat
Winhall
9.8 out of 10, Exceptional, (29 reviews)
"Great home, perfect weekend away at Stratton. Host was great and so was the property"
United States
Kevin M.
The Vermont A-Frame Mountain Retreat
A spacious kitchen with a large island, a stone fireplace, and wooden beams.

13. 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 €651
includes taxes & fees
1 Oct - 2 Oct
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.

14. 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 €734
includes taxes & fees
29 Sept - 30 Sept
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
An outdoor dining area with tables and umbrellas, a wooden fence, and a building with large windows and lights.

15. 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 €451
includes taxes & fees
7 Oct - 8 Oct
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
A room with a large window, a wooden table, two chairs, and a woven basket on the table.

16. 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, (1 review)
"Beautiful place Very spacious and super organized we love our stay "
United States
Rafael
The price is €487
includes taxes & fees
20 Oct - 21 Oct
Cozy 3 Bedroom Condo in the Heart of Manchester VT

17. 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 €639
includes taxes & fees
21 Oct - 22 Oct
The Birchwood Cabin - Stunning Mountain Views

18. 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 €508
includes taxes & fees
19 Oct - 20 Oct
Mountain Retreat with Outdoor Living Space and Ping Pong Table in Vermont
A large indoor swimming pool with wooden beams and a central decorative structure.

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

Equinox Getaway | Queen Guest Room w/ Sauna & Spa
Manchester Village Historic District
The price is €320
includes taxes & fees
25 Oct - 26 Oct
Equinox Getaway | Queen Guest Room w/ Sauna & Spa
A spacious kitchen with a central island, stainless steel appliances, and pendant lighting.

20. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is €664
includes taxes & fees
21 Oct - 22 Oct
1812 House, 2 Stays, 1 home
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

Brittany Motel

Brittany Motel

10/10 Excellent
"Place was nice we stayed in room next to amenities room it was noise all times at night doors slamming and dogs barking"
Scott 1-night trip
Posted 2 hours ago
Brittany Motel

Find out more about Bennington County

Holiday Homes in Bennington County

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