Family-friendly vacation rentals in Bennington

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Bennington

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Queensbury

4.99 out of 5 average rating, 159 reviews

Sunset Bay: Amazing waterfront w/ dock on 5 acres!

SUMMER 2025 left 4-nights: Sun, Aug 17-Thurs, Aug 21st 7-nights: Thurs, Aug 21st-Thurs, Aug 28 4-nights: Thurs, Aug 28-Mon, Sept 1 Amazing waterfront property on 5 acres with west-facing sunsets overlooking the water & mountains. Two-tiered deck, stone patio, & hot tub, open floor plan living/dining/kitchen. Private dock to swim off of and/or dock your own boat (May-Sept). Includes attached apartment with bedroom, kitchen, bathroom, and living room. Be close to everything yet away from it all.

Guest favorite

Home in Ludlow

4.89 out of 5 average rating, 132 reviews

1st floor, Okemo contemporary country 3 BR 2 BA

Family-friendly, pet-friendly, clean, comfortable, contemporary country ski cabin on Okema shuttle buss route in Ludlow, VT, a few minutes from mountain. Very easy access to outdoor activities: skiing, hiking, lakes, boating, hunting, snowmobiling, fly-fishing. Updated, comfortable, light filled ambiance. Great location, 10 minute walk to downtown (2 minute drive). Great for groups, couples, families. Recently renovated. New butcher block counter-tops and island, all new kitchen, new bathrooms.

Guest favorite

Home in Pittsfield

4.97 out of 5 average rating, 106 reviews

Berkshire Pontoosuc Lake- Modern and Updated

Lakefront Home for Rent. This home has been 100% remodelled! With a beautiful spot directly on Pontoosuc, the new kitchen, bathrooms, fireplace, and glass enclosed family room all benefit from the idyllic scenery. The home has 5 bedrooms and a convertible playroom with a futon for even more space. 2 bedrooms have bunk beds plus a full size bed in them. 2 bedrooms have king size beds and 1 has a queen. The master suite has an en-suite bathroom and a balcony overlooking the lake. Many upgrades!

Guest favorite

Cabin in Lake George

4.87 out of 5 average rating, 178 reviews

Cozy cabin with private beach, near village

Cabin with private beach, lake views, enclosed porch, deck with grill, and patio with fire pit and firewood. Fully equipped kitchen. Easy lake access to our quiet and private association beach and also Hearthstone State beach, both just short walk/drive. Included beach towels, chairs, umbrella, and cooler. Nearby boat/kayak rentals, hiking, biking, entertainment, and restaurants in Bolton and LG Village. SuperHost for 8 years. Sat - Sat weekly rental. Great monthly / seasonal discounts!

Guest favorite

Chalet in Athol

4.97 out of 5 average rating, 123 reviews

The Adirondack Retreat - Gore Skiing & Lake George

Stay in this charming chalet only 11 miles from Lake George and 19 miles to Gore Mountain! Sleeps up to twelve guests with 5 bedrooms and 2 bathrooms. No extra fees for more than two guests Walk into a home that says "Welcome to the Adirondacks!" with local antiques and hand carved cedar logs Main Floor: fully stocked kitchen, bath, bedroom with full bed, bedroom with twin/twin bunkbed Loft: master bedroom, bathroom, loft den Lower Level: game room, 2 bedrooms each with a twin/full bunkbed

Superhost

Cottage in Chester

4.9 out of 5 average rating, 156 reviews

Green Mountain Country Cottage

Four bedroom cottage centrally located within less than 35 min. of 4 ski resorts, and next to the former Tater Hill golf club. Access to snowmobile trail on site, X-country skiing, hiking, fishing, shopping, restaurants, state parks nearby. In summer and fall mushroom foraging is very productive. For history buffs there is a revolutionary war era cemetery next to the property. Sleeps 10 to 12. The cottage is only available to family groups or responsible adults over 25. NO PARTYING ALLOWED.

Guest favorite

Home in Weston

4.86 out of 5 average rating, 108 reviews

4 Bedroom Family Ski House w/ WiFi, cable!

This family heirloom sits tucked away in the trees just off of Chester Mountain Road. Short trips to Bromley, Okemo, Stratton and Magic Mountains. Sleeps 8 comfortably with room for up to 10 on pull out couches. You will fall in love with the retro feel of this house, it's straight out of the 1980's, and has kept that charm over the years. We have consistently updated it with all of the amenities needed to relax, including Air Conditioning, High Speed wifi, Cable, big screen TV and sound bar.

Superhost

Condo in Ludlow

4.8 out of 5 average rating, 163 reviews

Winter Paradise —Ski-ON/Ski-OFF Okemo Getaway

Perched on Okemo mountain, step to the trails and start your day with no need to ski to the base. You will be on the best ski/on-ski/off location directly to Sunburst 6 Bubble, Sachem or South Ridge Quads & boarding park lifts; while having everything you might need for a cosy and convenient family stay. That includes a fully-equipped kitchen and a living room with games for your entertainment, a private balcony, laundry facilities and shared resort-style amenities at Winterplace with pool.

Superhost

Cottage in Queensbury

4.84 out of 5 average rating, 195 reviews

Stonewall Cottage on Sandy Bay: Fireplace & Views

Known by locals as the charming Stonewall Cottage on Cleverdale Point with views of Sandy Bay. Perfect for couples & families who want to get away from it all on the east side of the Lake George. Private fenced in backyard with picnic table, Adirondack chairs and new Weber grill. Walk to Sans Souci restaurant, Cleverdale Country Store & Boats by George for paddle boarding and boating. Enjoy fast wireless internet (100Mbps). Close to hiking, strolls in neighborhood and restaurants.

Guest favorite

Home in Salem

4.98 out of 5 average rating, 185 reviews

Magical Farm Getaway - a must visit!

Beautifully restored 18th century farmhouse situated on 4.6 private acres within a 180 acre working farm. Five bedrooms, wood stoves, ample living space, and a cheery sun room with gorgeous views make this house one of a kind. Our backyard features an in-ground, heated, salt water swimming pool (open May to mid-Oct), fire pit (open year-round), large outdoor dining table, gas grill, and a deck with lounge seating and jacuzzi (open year-round). Parties and events are not allowed.

Guest favorite

Rental unit in Earlton

4.93 out of 5 average rating, 290 reviews

Sweet Farm Stay

Come stay in a fully-outfitted barn apartment with views that look out over the pony paddock and the sheep pasture! For an extra fee we also offer… ** FARM CAMP** perfect for kids & families. 2 hours of farm chores, pony-riding, crafts every morning that you are here. ** CRAFT RETREATS** All-inclusive weekend with up to 7 guests. Wool / wood / kitchen craft. Work on the farm, MAKE stuff, and enjoy the outdoors. DM for more info. Find us on ig — honeyhollowfarmstay!

Guest favorite

Rental unit in Chester

4.89 out of 5 average rating, 491 reviews

Beautiful 2 Bedrooms in Mountains w/ full kitchen

Ready for a Vermont getaway? In heart of ski area w/ A+restaurants & charming villages are two cozy bedrooms on 2nd fl of larger apt complex. Each bedroom has separate toilet/sink room, shared shower room for your and your guests alone. Hallway living room at one end with 2 couches, desk and TV Other end is full compact kitchen with dishwasher, stove and over, full size refrigerator, coffee maker and microwave.