
Family-friendly holiday rentals in Bennington County
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Bennington County
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Edelweiss Cottage, Manchester VT
Welcome to Edelweiss, a beautiful guest cottage in Manchester Vermont. Our idyllic cottage is nestled into the hillside at the base of Mount Equinox. The two story cottage boasts a stunning stone fireplace and large windows overlooking the tiered landscape and Green Mountains in the distance. We are located minutes to Manchester viliage, shopping outlets, Equinox Resort, Hildene, and the Equinox Skyline drive. We are 20 minutes to Bromley and 35 minutes to Stratton and Magic Mountain.
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Warm Brook Farm | Farmhouse & Gardens | Hot Tub
Step into the timeless charm of Warm Brook Farm, a beautifully restored 18th-century farmhouse in Southern Vermont. Once a lively inn and stagecoach stop in the early 1800s, this elegant retreat combines historic character with modern luxury. Enjoy a genuine chef's kitchen, award-winning gardens, and upscale amenities throughout. We cover your Airbnb service fees — the price you see is what you pay. An inviting getaway to relax, explore, and create lasting memories with family and friends.
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Beautiful timber-frame treehouse
The timber frame treehouse is a perfect couples retreat. The home is custom built with hardwood maple trees cut down and milled right on the property. The deck has a barrel sauna, cold or hot cedar soaking tub, a propane fire pit, a wood burning chiminea fire pit, and a bar top for outdoor dinning. The inside has a stone fireplace, fully equipped kitchen, tile shower, projector with dvds, books, board games, chandelier, and dimmable lighting for any mood. This home is truly one of a kind.
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Southern Vermont Home
Beautiful home that offers privacy on over one acre of land. It is only a short drive to the conveniences of downtown shopping, restaurants, Bennington College, and much more. This house is 35 minutes from Manchester's famous outlets, 20 minutes from Williamstown, MA, and 45 minutes from Albany, NY. Bromley and Mount Snow ski areas are 40 minutes. The home has wonderful finishes and you will feel right at home upon arrival. Please come explore Vermont from our country escape!
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The Birchwood Cabin - Stunning Mountain Views
Welcome to the Birchwood Cabin - a beautiful log cabin with stunning mountain views! Relax in the hot tub overlooking the mountains or enjoy hot chocolate by the fire. Play a game of pool or shuffleboard downstairs. The Birchwood Cabin is in a peaceful, quiet location but is only a 10-minute drive to Manchester, if you'd like to go shopping or grab a bite to eat! Hit the slopes at Bromley Mountain or Stratton Mountain or in the warmer weather head to The Equinox for a round of golf!
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Cozy Cabin at Frog Pond Farm
Cozy 500sq ft passive solar cabin on our small farm, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/gardens or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.
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The Gate House--Experience Vermont!
The Gate House is a historic property located at the foothills of Mt Anthony. Built in 1865, the original structure of the house served as the gate house to the Colgate Estate, one of the most beautiful properties in Southwestern Vermont. Our home is just a few short miles to downtown where you can find local restaurants and breweries. We are not far from some of the best skiing/riding in the Northeast at Mt Snow, Bromley, Stratton and Prospect Mountains.
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Southern Vermont Cottage
Cozy but not small, this home is in a peaceful location with plenty of beds to house your family as you visit beautiful Vermont for skiing, hiking, swimming or shopping. Manchester Center, Dorset and Bennington are all within a 20 minute drive. Southern VT boasts many of the state's best restaurants and shopping, & the Southern Vermont Arts Center. Also nearby - Dorset Theater Playhouse, Dorset Quarry, Mt Equinox, Bromley Mountain, Mt. Snow and Stratton!
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Schoolhouse Spa Retreat on a Vermont Farm
Escape to our historic and lovingly-renovated schoolhouse on a 250-acre verified-regenerative farm, where Green Mountain views meet modern comfort. Unwind in your private hot tub and barrel sauna after exploring farm trails, then fall asleep to the gentle sounds of sheep grazing in the pastures below. This is Vermont at its most authentic—working farm life with all the luxury. Level 2 EV charger, in-unit washer/dryer, and ductless AC for summer comfort.
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Cozy, bright 3-bedroom Cottage with fireplace.
Cozy, spacious brook-side cottage with 3 bedrooms, 2 baths, fully-equipped kitchen, fireplace, and serene, 382-acre country setting. Colorful artwork, designer furnishings, and well-appointed kitchen and bathrooms will make you feel welcome and at home. Historic charm of Bennington ten minutes away. NYC (182 miles); Boston (118); Mt. Snow (32); Prospect Mountain (13). Close to MASS MoCA (22), Tanglewood (49) and Manchester outlets (32).
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The Vermont Farmhouse|Hiking|Dog Trails|Village
The Luxury of Slowing Down — Vermont Style. Leave the rush behind and feel rested, reconnected and renewed at our dog-friendly, beautifully restored 1860s farmhouse. Wide-plank floors, sun-filled rooms and modern comforts create a warm, impeccably clean retreat. Walk across the road into 280 acres of peaceful Mile Around Woods trails, or stroll into historic North Bennington for cafés and shops. It's all right at your doorstep.
Indoor spacesFamilyTV

White Rock Farm
White Rock Farm is a working sheep farm in Bennington VT, part of the scenic and historic Valley of Vermont and surrounded by the Green and Taconic Mountains. The farm is a place where successive generations have been stewards of its 295 acres. First established in 1828, today it remains a working farm that includes livestock, maple syrup, and timber production.
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Popular amenities for Bennington County family-friendly rentals
Family-friendly home rentals with a hot tub

The House of Pi
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Mountain view chalet with hot tub & fire pit!
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Chalet 1mi to Mount Snow with theater and hot tub
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A frame cabin with Hot tub near Stratton, VT
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Vermont Dream Cabin~70 Acres w/Hot Tub & Fireplace
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Mt Snow Chalet: Peaceful Escape w/Hot Tub
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In Town Manchester Studio w/ Loft Bedroom.
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Brook House: Hot Tub, Fire Pit, Ping Pong, Mt Snow
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Family- and pet-friendly home rentals

Quaint One-Story Vermont House with Mountain View
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Cabin-Swim-Fire Pit-Sauna-7min to Stratton-DogsOK
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5BR Rustic Mountain Sanctuary Dome Home
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Log Cabin King Beds AC Near Hike Bike Swim Golf!
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Designer Chalet w/ Mountain Views close to it all
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The Mountain A-Frame at Mount Snow
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The Rafters Lodge
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The Equinox Cottage
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Family-friendly home rentals with a pool

Family-friendly 4BR | Pools Hot Tub | Near Mt Snow
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Beautiful Bromley/Manchester VT Retreat w/hot tub
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Log Cabin Near Stratton/Mt Snow
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~10% OFF~Walk To Mountain~Amenities
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Leonard’s Log - Private Hot Tub, Fire Pit, A/C
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Slopeside Condo @ Seasons on Mt Snow (Ski-In/Out)
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Base of M.S. All Seasons Fun. Deck/HotT/Pool/Sauna
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Mt Snow Ski In/Out at Seasons
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- Family-friendly rentals Vermont
- Family-friendly rentals United States
- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- June Farms
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- West Mountain Ski Resort
- Bousquet Mountain Ski Area
- Hildene, The Lincoln Family Home
- Killington Resort
- Rensselaer Polytechnic Institute
- Bromley Mountain Ski Resort
- Emerald Lake State Park
- Saratoga Spa State Park
- MVP Arena
- New York State Museum
- Massachusetts Museum of Contemporary Art
- Trout Lake
- Mount Greylock
- Crossgates Mall





