Bennington County holiday homes

We found 1,846 holiday rentals — enter your dates for availability

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April 2025

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Select from 343 houses, 50 flats and other holiday rentals to find the perfect place for your stay in Bennington County. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include air conditioning and a pool. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Popular Bennington County destinations on Bookabach

Holiday rentals with weekly discounts - Bennington County

Showing deals for:18 Jul - 25 Jul

Beautiful 4-season ski chalet on Okemo less than a mile to ski base

Exceptional

(125 reviews)

Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!

Ludlow, VT

14% off

NZ$563 per night

includes taxes & fees

Exceptional

(20 reviews)

Authentic Vermont Log Cabin Between Mount Snow and Stratton - No monthly rentals

Wardsboro, VT

8% off

NZ$548 per night

includes taxes & fees

Exceptional

(6 reviews)

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

West Dover, VT

8% off

NZ$2,260 per night

includes taxes & fees

Exceptional

(13 reviews)

Hidden Pond Farm 300 Acre Paradise directly on Famed Batten Kill River

Arlington, VT

8% off

NZ$1,721 per night

includes taxes & fees

Front of cottage. Easy 2 parking spaces just outside in front

Exceptional

(10 reviews)

Charming, Sweet Cottage Danby Manchester, Stratton, Bromley, Dorset, Okemo

Danby, VT

8% off

NZ$502 per night

includes taxes & fees

Welcome to our home near Mount Snow with a hot tub!

Exceptional

(31 reviews)

Mount Snow Area Home with a Hot Tub, Fire Pit, Set Back in the Woods!

Wardsboro, VT

8% off

NZ$1,780 per night

includes taxes & fees

Stacked-stone fireplace and french doors.

Exceptional

(133 reviews)

Luxury home in the heart of Manchester. Walk to shops; minutes to mountains.

Manchester, VT

8% off

NZ$1,945 per night

includes taxes & fees

The 30' lap pool is right outside your door.

Exceptional

(80 reviews)

FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

Pownal, VT

8% off

NZ$371 per night

includes taxes & fees

Superior views of Mount Snow, as seen here from the main living room.

Exceptional

(14 reviews)

Two minutes to Mount Snow! Spacious, beautiful home.

West Dover, VT

8% off

NZ$2,412 per night

includes taxes & fees

Find spaces that suit your style

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Find the best place to stay - Bennington County

1828 Vermont Cottage Feet From The Famous Battenkill River

Sleeps 5 · 3 bedrooms · 1+ bathroom

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Bennington County getaway

Learn about the unique charm of Bennington County with a stay in a holiday home rental. This city has something for everyone. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Bennington County

Are you searching for attractions to visit in the area? Venture out of your holiday home and check out everything that makes Bennington County a fun place to get away to. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

Prospect Mountain Nordic Ski Center (6 mi / 9.6 km)
Prospect Mountain Cross-Country Ski Center (6.4 mi / 10.2 km)
Sugar Shack (14.5 mi / 23.4 km)
Mount Snow (15.1 mi / 24.3 km)
The Hermitage Club (15.1 mi / 24.3 km)
Waubeeka Golf Links (15.4 mi / 24.9 km)

Exploring the natural features in Bennington County

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Bennington County is a great place to spend some time outside. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city centre:

Lake Shaftsbury State Park (9.8 mi / 15.8 km)
Windsor Lake Park (14.4 mi / 23.1 km)
Grafton Lakes State Park (14.6 mi / 23.5 km)
Taconic Lake (14.7 mi / 23.7 km)
Harriman Reservoir (15.6 mi / 25.1 km)
Mount Greylock State Reservation (16.3 mi / 26.3 km)

Frequently asked questions

What is the best area to stay in Bennington County when booking a holiday home?

If you’re thinking about a stop in Bennington County, Bennington is among the more sought-after areas to book a holiday property. While you’re here, keep busy by discovering leading sights like Bromley Mountain Ski Resort and Equinox Preservation Trust.

What is the most popular type of holiday home accommodation in Bennington County?

Houses are the most popular type of holiday home in Bennington County, according to our data. Even if you’ve got something a little different in mind, Bookabach has holiday homes in all sizes and shapes. Look through our options to find your perfect match.

How much does it cost to rent a holiday home in Bennington County?

Season, property type and length of stay are among the factors that can influence the price of a holiday home. Simply click on your dates of travel to find your ideal escape. From cosy country cottages to expansive luxury villas, all Bookabach holiday homes offer amazing value.

How much does it cost to rent a beach house in Bennington County?

The average price for a holiday home near the beach in Bennington County will depend on when you’ll be there and the size and style of property you want. You can find prices easily and quickly on Bookabach by entering your travel dates and destination. Then use the handy filters to select the number of bedrooms and amenities that you require, like air conditioning, WiFi and a hot tub.

Are there large group holiday homes in Bennington County?

You’ll discover 158 holiday homes in Bennington County that can accommodate a group of 10 or more people. Whether you’re planning a trip with extended family or a special event like a birthday party, there’s plenty of space to get your favourite people together under the same roof.

What are the top attractions for families in Bennington County?

You’ll find loads of amazing things to see and do with the family in Bennington County, such as:

Prospect Mountain Cross-Country Ski Centre
Vermont Summer Festival
Bromley Mountain Ski Resort

Can I find two-bedroom holiday homes in Bennington County?

Take your pick of 40 two-bedroom homes in Bennington County. Put the kids in the second room or fill it with a couple of your nearest and dearest friends. There’s space for whoever’s fortunate enough to be coming along.

Are there holiday homes with WiFi in Bennington County?

You’ll find 175 holiday homes with WiFi in Bennington County. If you’d like to disconnect from the world on your break, but still need to be connected to the internet, these properties have just what you need. Narrow your search by applying the WiFi filter on Bookabach.

How old do you have to be to rent a holiday home in Bennington County?

The minimum age requirements can differ across properties on Bookabach, so look at the rules of the holiday home in Bennington County you’re interested in. But usually, it’s 16, 18 or 21.

How long can I rent a holiday home in Bennington County for?

How long you can rent a holiday home in Bennington County varies according to the property. Just enter your preferred dates to see a list of options offering extended stays. With plenty of features like washing machines and kitchens, as well as some offering discounted weekly or monthly prices, you’re sure to find someplace just right to call your home away from home in Bennington County.