Bennington County Holiday Rentals

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Top cities in Bennington County

Check prices for these dates

Our top choices for Bennington County holiday rentals

1. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (15 reviews)
"Absolutely wonderful place to stay. Quiet, clean, comfortable and close to a lot of things while feeling secluded. Owner communicated quickly and entry was easy. Loved every minute of our stay."
United States
Jeri R.
The price is HK$911
HK$1,538 total
includes taxes & fees
23 Nov - 24 Nov
Cozy Home in Pownal VT

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 HK$902
HK$2,237 total
includes taxes & fees
15 Nov - 16 Nov
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

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 HK$1,001
HK$4,179 total
includes taxes & fees
16 Nov - 17 Nov
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

4. West Barn Suite at Hubbell Homestead - Mountain Views & Jetted Tub

West Barn Suite at Hubbell Homestead - Mountain Views & Jetted Tub
Bennington
The price is HK$1,765
HK$2,135 total
includes taxes & fees
13 Nov - 14 Nov
West Barn Suite at Hubbell Homestead - Mountain Views & Jetted Tub

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

ADA King Room w/ Roll-In Shower & Views
Manchester Village Historic District
The price is HK$1,789
HK$2,128 total
includes taxes & fees
23 Nov - 24 Nov
ADA King Room w/ Roll-In Shower & Views

6. 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 HK$1,518
HK$2,025 total
includes taxes & fees
17 Nov - 18 Nov
Spacious apartment in beautiful, historic Arlington VT

7. Historic Home with Colonial Charm in Manchester

Historic Home with Colonial Charm in Manchester
Manchester
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful old historic house, a pleasure and treasure to get to stay there!"
United States
Mary Ann E.
The price is HK$864
HK$2,979 total
includes taxes & fees
1 Dec - 2 Dec
Historic Home with Colonial Charm in Manchester

8. Cozy Bromley Retreat — Ski-In, Ski-Out

Cozy Bromley Retreat — Ski-In, Ski-Out
Bromley Mountain
9.4 out of 10, Exceptional, (21 reviews)
"The place was clean and had all the essentials. Right across from pool and great stay."
United States
Andrew P.
The price is HK$1,128
HK$3,395 total
includes taxes & fees
16 Nov - 17 Nov
Cozy Bromley Retreat — Ski-In, Ski-Out

9. Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown

Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown
Pownal
10.0 out of 10, Exceptional, (41 reviews)
"We enjoyed our stay! The home was clean, well-stocked, and very comfortable. I loved the serenity of the location. We took walks on trails through the forest and enjoyed the peace and quiet."
United States
Claudette R.
The price is HK$2,471
HK$4,639 total
includes taxes & fees
19 Nov - 20 Nov
Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown

10. 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, (4 reviews)
"Beautiful accommodations. Great communication with host."
United States
Peggy S.
The price is HK$2,118
HK$4,566 total
includes taxes & fees
17 Nov - 18 Nov
Cozy 3 Bedroom Condo in the Heart of Manchester VT

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 HK$1,231
HK$3,430 total
includes taxes & fees
1 Dec - 2 Dec
Modern Mountain Retreat w/ Chef’s Kitchen

12. Tranquil Cabin Hideaway with Firepit and Riverfront Views on the Green River in Vermont

Tranquil Cabin Hideaway with Firepit and Riverfront Views on the Green River in Vermont
Sandgate
The price is HK$3,040
HK$3,725 total
includes taxes & fees
15 Nov - 16 Nov
Tranquil Cabin Hideaway with Firepit and Riverfront Views on the Green River in Vermont

13. The Birchwood Cabin - Stunning Mountain Views

The Birchwood Cabin - Stunning Mountain Views
Sunderland
10.0 out of 10, Exceptional, (6 reviews)
"Excellent host very responsive. Beautiful cozy cabin with all the amenities you need. Highly recommend! "
United States
Robert V.
The price is HK$2,082
HK$4,994 total
includes taxes & fees
8 Dec - 9 Dec
The Birchwood Cabin - Stunning Mountain Views

14. Two bedroom Condo With Mountain View And Fireplace

Two bedroom Condo With Mountain View And Fireplace
Stratton
9.2 out of 10, Wonderful, (5 reviews)
"Very comfortable stay for four adults. The kitchen is well appointed, great beds and showers. Easy, prompt communication with owner. "
United States
Marie B.
The price is HK$1,913
HK$5,467 total
includes taxes & fees
15 Nov - 16 Nov
Two bedroom Condo With Mountain View And Fireplace

15. Wonderful hilltop house with breathtaking views

Wonderful hilltop house with breathtaking views
Dorset
The price is HK$3,530
HK$4,165 total
includes taxes & fees
29 Nov - 30 Nov
Wonderful hilltop house with breathtaking views

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

Equinox Getaway | Queen Guest Room w/ Sauna & Spa
Manchester Village Historic District
The price is HK$1,648
HK$1,963 total
includes taxes & fees
23 Nov - 24 Nov
Equinox Getaway | Queen Guest Room w/ Sauna & Spa

17. Cupola Suite w/ Mountain View + Spa Access

Cupola Suite w/ Mountain View + Spa Access
Manchester Village Historic District
The price is HK$2,711
HK$3,221 total
includes taxes & fees
18 Nov - 19 Nov
Cupola Suite w/ Mountain View + Spa Access

18. East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub

East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub
Bennington
The price is HK$1,765
HK$2,135 total
includes taxes & fees
13 Nov - 14 Nov
East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub

19. Mountain Chalet, sleeps 8, with hot tub

Mountain Chalet, sleeps 8, with hot tub
Peru
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful place. Comfortable and well furnished. "
United States
Michael B.
The price is HK$2,084
HK$5,396 total
includes taxes & fees
2 Dec - 3 Dec
Mountain Chalet, sleeps 8, with hot tub

20. 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 HK$2,581
HK$4,086 total
includes taxes & fees
1 Dec - 2 Dec
New! Vermont Getaway! Stratton - close to skiing!
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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