Holiday Rentals in Bennington County

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Top cities in Bennington County

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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, (14 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 €179
includes taxes & fees
15 Nov - 16 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.
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 €467
includes taxes & fees
10 Nov - 11 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 €250
includes taxes & fees
22 Nov - 23 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 €253
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 €238
includes taxes & fees
10 Nov - 11 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 €344
includes taxes & fees
10 Nov - 11 Nov
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 €398
includes taxes & fees
10 Nov - 11 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 €538
includes taxes & fees
11 Nov - 12 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 €527
includes taxes & fees
10 Nov - 11 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 €372
includes taxes & fees
10 Nov - 11 Nov
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 €432
includes taxes & fees
10 Nov - 11 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, (4 reviews)
"Excellent host very responsive. Beautiful cozy cabin with all the amenities you need. Highly recommend! "
United States
Robert V.
The price is €567
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.
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 €472
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 €229
includes taxes & fees
6 Dec - 7 Dec
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 €353
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 €250
includes taxes & fees
22 Nov - 23 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.
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 €471
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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Everything you need to know about Bennington County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Bennington County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Bennington County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Bennington County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Bennington County. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Bennington County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Bennington County holiday rentals we have selected for you start as low as €178 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Bennington County rentals

At Expedia, we put the best Bennington County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Bennington County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Bennington County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Bennington County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.