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

Bennington County holiday rentals

We found 1,942 holiday rentals — enter your dates for availability

Select from 340 houses, 62 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 Stayz

A white building with red trim and a sign that reads "The Hidden Jewel."

Manchester

A red covered bridge over a river with greenery and yellow flowers around.

Bennington

A street lined with white buildings and yellow autumn trees.

Manchester Center

A restaurant named 'Dot's Restaurant' with a porch and flower boxes.

Wilmington

A forest with a moss-covered rock and a stream.

Peru

A red barn with a white steeple, surrounded by green grass and yellow flowers, with mountains in the background.

Dorset

Holiday rentals with weekly discounts – Bennington County

Showing deals for:11 Dec - 18 Dec

A beautiful brook that runs through our lot

Exceptional

(101 reviews)

New Lakefront Log Home

Wilmington

12% off

AU$5,789

for 7 nights, 1 chalet

AU$827 per night

includes taxes & fees

Exceptional

(82 reviews)

Beautiful Lakeview Log Cabin on 60-Acre Property

Peru

8% off

AU$30,595

for 7 nights, 1 home

AU$4,371 per night

includes taxes & fees

Exceptional

(16 reviews)

Chalet Mount Snow/Stratton Skiing/hiking

East Dover

7% off

AU$3,046

for 7 nights, 1 chalet

AU$435 per night

includes taxes & fees

Dining area, 10 Chairs are now black, Need a new picture!

Exceptional

(243 reviews)

Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews

Wilmington

8% off

AU$6,929

for 7 nights, 1 home

AU$990 per night

includes taxes & fees

Exceptional

(12 reviews)

Forest Lodge - Near 6 Ski Resorts

Jamaica

8% off

AU$12,278

for 7 nights, 1 home

AU$1,754 per night

includes taxes & fees

Exceptional

(8 reviews)

Views of Stratton, Minutes from the Slopes, EV Charging Level 2

Bondville

8% off

AU$15,406

for 7 nights, 1 home

AU$2,201 per night

includes taxes & fees

Exceptional

(40 reviews)

Wishing Well Cabin

Jamaica

8% off

AU$3,553

for 7 nights, 1 cabin

AU$508 per night

includes taxes & fees

A look at the main floor family room from above.

Welcome to our 9 bedroom luxury home in the heart of Southern Vermont!

Hot tub and firepit are great after a day of fun.

Exceptional

(22 reviews)

September & October available! Luxury 9BRs Stratton Estate. Pool, Mountain Views

Bondville

8% off

AU$25,910

for 7 nights, 1 home

AU$3,701 per night

includes taxes & fees

Build a cozy fire in our wood fireplace, watch the game or play pool!

Beautiful period woodwork and Victorian details

Gourmet kitchen has everything you need to prepare delicious meals

Exceptional

(157 reviews)

Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!

Williamstown

7% off

AU$8,167

for 7 nights, 1 home

AU$1,167 per night

includes taxes & fees

View of the Main house living room from the kitchen bar

Main house top floor river room with sounds of the river out the windows.

View of the main house from the creek on the property.

Exceptional

(38 reviews)

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Wardsboro

8% off

AU$21,752

for 7 nights, 1 home

AU$3,107 per night

includes taxes & fees

Exceptional

(255 reviews)

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Bondville

8% off

AU$2,444

for 7 nights, 1 cottage

AU$349 per night

includes taxes & fees

Exceptional

(45 reviews)

Bennington Guest Farmhouse

Bennington

8% off

AU$2,581

for 7 nights, 1 home

AU$369 per night

includes taxes & fees

Master bedroom is 12X20 and overlooks our beautiful river - private bathroom

One of a kind woodwork, beautiful handmade furniture and built ins.....

Inside, Outside - take your pick - it's always magical

Exceptional

(53 reviews)

One of a Kind Post and Beam Home on Private 100 acre Island

Jamaica

8% off

AU$9,030

for 7 nights, 1 home

AU$1,290 per night

includes taxes & fees

Large open-concept living and kitchen area

Exceptional

(18 reviews)

Leonard’s Log Cabin— Mt. Snow/Stratton Ski House

Wardsboro

8% off

AU$5,353

for 7 nights, 1 cabin

AU$765 per night

includes taxes & fees

Exceptional

(55 reviews)

Skylight Ski Lodge VT Rustic Chic Near Stratton

Bondville

8% off

AU$14,312

for 7 nights, 1 home

AU$2,045 per night

includes taxes & fees

Exceptional

(78 reviews)

Western Mountain Lodge on River and Close to Stratton

Jamaica

20% off

AU$9,971

for 7 nights, 1 home

AU$1,424 per night

includes taxes & fees

Exceptional

(27 reviews)

Bear Pass Bunkhouse

Manchester

8% off

AU$3,034

for 7 nights, 1 home

AU$433 per night

includes taxes & fees

Exceptional

(7 reviews)

Vermont Summer Escape - Sleeps 8 with FirePit, Hot Tub, and Pet Friendly!

Bondville

8% off

AU$23,821

for 7 nights, 1 home

AU$3,403 per night

includes taxes & fees

Bedroom #2 Queen bed with large windows & french doors

Open living room with french doors, huge windows & vaulted ceiling

Exceptional

(7 reviews)

Frank Lloyd Wright inspired Private, mountain views, wheelchairs accessible

Weston

8% off

AU$5,772

for 7 nights, 1 home

AU$825 per night

includes taxes & fees

Enjoy the family friendly open concept living area with soaring ceilings

Welcome to Bear Lair Lodge!

Photo by : @dirtandglass

Exceptional

(30 reviews)

Mount Snow Chalet-modern family home, chefs kitchen, gameroom, Clubhouse pool

Wilmington

8% off

AU$7,202

for 7 nights, 1 home

AU$1,029 per night

includes taxes & fees

Exceptional

(57 reviews)

Modern mountain home - Vermont Ski House close to Stratton

East Dorset

8% off

AU$9,953

for 7 nights, 1 home

AU$1,422 per night

includes taxes & fees

Kitchen and dining Area - seats 9 with bench / 2 at counter

Exceptional

(32 reviews)

Perfect Get-Away House - 6 Miles from Stratton & Mount Snow

West Wardsboro

5% off

AU$8,626

for 7 nights, 1 home

AU$1,232 per night

includes taxes & fees

Exceptional

(39 reviews)

Cozy Manchester Getaway with Amazing Views!!!

Bondville

7% off

AU$4,793

for 7 nights, 1 home

AU$685 per night

includes taxes & fees

Exceptional

(31 reviews)

Secluded large country home for big groups with giant open yard for outdoor fun.

Whitingham

20% off

AU$3,476

for 7 nights, 1 home

AU$497 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Cabin

Cottage

Villa

Chalet

Find the best place to stay - Bennington County

1828 Vermont Cottage Feet From The Famous Battenkill River

Sleeps 5 · 3 bedrooms · 1+ bathroom

Premier Host

Mountains, pond, old barn, hiking trails- quintessential Vermont

Sleeps 7 · 2 bedrooms · 1 bathroom

Premier Host

Historic 1769 Vermont Home Near Manchester

Sleeps 10 · 6 bedrooms · 5 bathrooms

1920's Bennington Vermont Guest Barn

Sleeps 7 · 3 bedrooms · 1 bathroom

Premier Host

Mountain Sanctuary Dome Rustic Solitude 5BR

Sleeps 12 · 5 bedrooms · 2 bathrooms

Premier Host

Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester

Sleeps 8 · 3 bedrooms · 1+ bathroom

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 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)
The Hermitage Golf Club (15.7 mi / 25.3 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)
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)
Mount Greylock (16.7 mi / 26.9 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, Stayz 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 Stayz 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 Stayz 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 Stayz.

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

The minimum age requirements can differ across properties on Stayz, 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.

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