
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.

Country Colonial Home with rolling fields & stream
This wonderful colonial home offers wide open space on 21 acres of rolling fields with paths leading to the Green River. In the summer build your own dam or in the winter cross country ski along the edges of the stream and get a full view of the West Arlington valley. Swearing Hill is located within a mile of an old country store for all types of immediate supplies. The town of Arlington is 5 miles away, and Manchester, Vt. Is 14 miles, offering golfing, shopping, and wonderful restaurants.
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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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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 Vermont Farmhouse|Hiking|Dog Trails|Village
Experience the magic of this restored 1860s Vermont farmhouse, where historic charm meets modern luxury. This 1,700 sq ft retreat offers 2 cozy bedrooms, 2.5 baths, and sun-drenched living spaces. Relax in Adirondack rockers on the expansive deck, explore 280 acres of woodland trails right outside your door, or take a short stroll into the village. Later, gather at the fire pit for s’mores under the stars. Welcome to your quintessential New England escape at The Vermont Farmhouse.
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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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The House of Pi
WE now pay your 15.5% Guest Service fee!!! Welcome to The House of Pi π aka Lakefront Loft. One of a kind custom built 34 foot high raised container home overlooking a beautiful southern VT lake with direct lakefront property with your own private dock and Kayaks. Our spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views. Hot Tub and Custom Cedar Sauna!
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Modern 3-bedroom A-frame in Londonderry w/ Pond
This 1970s A-Frame has been newly renovated and is ready to host guests. This home is located on a 2.6 acre property complete with a swimmable pond , outdoor firepit (snow dependent) and dining al fresco. It's located only a few minutes away from amenities such as Londonderry Market, Pingree Park, Lowell Lake and several restaurants. For skiing, this home is in proximity to Magic (8min), Bromley (9min), Okemo (25 min) and Stratton (20 min).
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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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Cozy Modern Sugar House with spectacular views.
This beautiful Vermont home sits on 25 acres with spectacular views. We moved this sugar house structure to this land and had an architect adapt it to its surroundings. It has three walls of windows that display the amazing views. The house is surrounded by Mount Anthony hiking trails and a gorgeous pond. The location is a 5 minute drive to town or a lovely 20 minute walk.
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Popular amenities for Bennington County family-friendly rentals
Family-friendly home rentals with a hot tub

Mountain view chalet with hot tub & fire pit!
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Schoolhouse Spa Retreat on a Vermont Farm
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HYGGE HOUSE Luxe HotTub, Sauna, Fall Leaves, Ski
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Mt Snow Chalet: Peaceful Escape w/Hot Tub
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A frame cabin with Hot tub near Stratton, VT
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Brook House: Hot Tub, Fire Pit, Ping Pong, Mt Snow
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MOUNTAIN NEST, views, Manchester, hot tub,
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Vermont Dream Cabin~70 Acres w/Hot Tub & Fireplace
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Family- and pet-friendly home rentals

The Rafters Lodge
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White Doe Farm •Lovingly restored antique farmhome
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Log Cabin King Beds AC Near Hike Bike Swim Golf!
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Ski and Play in Manchester Center!
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The Farm Cottage- Quiet 1BR on Hobby Farm
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Cabin-Swim-Views-Firepit-7 min to Stratton-Dogs OK
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Quaint One-Story Vermont House with Mountain View
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5BR Rustic Mountain Sanctuary Dome Home
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Family-friendly home rentals with a pool

Modern Cottage between Stratton and Mount Snow VT
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Cozy 4BR Cabin | Pools & Hot Tub | Near Mt Snow
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Walk to Mt. Snow-Spa-Summer Pool
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Slopeside Condo @ Seasons on Mt Snow (Ski-In/Out)
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Premier Stratton Village Location - Pool & Hot Tub
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Beautiful Bromley/Manchester VT Retreat w/hot tub
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Cozy condo within walking distance to the slopes.
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~10% OFF~Walk To Mountain~Amenities
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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
- Magic Mountain Ski Resort
- June Farms
- Pico 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
- National Museum of Racing and Hall of Fame
- Trout Lake
- Crossgates Mall





