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Family-friendly vacation 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.

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Home in Readsboro

4.86 out of 5 average rating, 124 reviews

Relax in Peaceful Vermont! (Pet Friendly)

Beautiful Country Home, nestled in Vermont's Green mountains, panoramic views, with good access by the road. A babbling brook to lull you asleep from the master bedroom, and a clawfoot soaking tub, fully stocked house. Hiking, antiques, shops, lakes, picnics, covered bridges, cozy local inns, mountain views! Enjoy Vermont! Scenic roads, Mt. Snow, VAST trails, Mt.Greylock, Mass MOCA museum, nearby N.Adams, MA, Berkshires. Bennington Wilmington & Mt. Snow. PEACEFUL & PERFECT Vermont getaway! ☺

Cabin in Londonderry

4.94 out of 5 average rating, 334 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery & hiking right outside your front door. The Cabin has an open floor plan with a full bath, galley kitchen & dining/living area with pullout futon couch that converts into a 2nd bed. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Cabin in Jamaica

4.89 out of 5 average rating, 369 reviews

Forest Cabin-Swim-Views-Fire Pit-7 min to Stratton

Authentic post & beam cabin surrounded by forest. Private location off a quiet road, 3 miles to Stratton Sun Bowl (a 7-minute drive). Swimming hole at babbling brook on property, fire pit, hammock on porch, propane BBQ, picnic table, forest views. VCR & videos, turntable & records, games, Satellite Internet & WiFi 20-100 mbps, TV & Roku. Staircase to loft, gas heat, wood stove, pellet stove. Full kitchen. Easy to use, odorless composting toilet. Dog friendly (sorry, no cats due to allergies).

Rental unit in Dorset

4.99 out of 5 average rating, 185 reviews

Vermont barn apartment

The Barn Apartment at Sykes Hollow Farm is in the gorgeous Mettowee Valley with 5 friendly horses, entertaining chickens, mountain views and a host who cares about you. The farm is a quiet, private, peaceful place with 30 acres to roam, but still close to Dorset and Manchester. Fields, mountains and a pond are all here. Good for couples and solo travelers who want an amazingly beautiful setting. This listing is more than a rental... it's an entire farm. Powered by solar to help the planet!

Chalet in Dover

4.92 out of 5 average rating, 285 reviews

A charming VT chalet

Charming chalet nestled in the Mt Snow valley. Relax to the sound of a babbling brook in the back yard while you hang around a stone fire pit! Unwind in the quiet serenity of this country home complete with fully equipped kitchen with a newly installed gas fireplace , a comfy open living room with flat screen cable tv & DVD player Roko & High speed Internet . We have a lock box located on the post near the front entrance. combo provided upon arrival . Washer & dryer located on first level.

Cottage in Shaftsbury

4.98 out of 5 average rating, 636 reviews

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

This newly-renovated historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 350 acre property.

Cabin in Shaftsbury

4.9 out of 5 average rating, 399 reviews

The LoveNest -Charming private cabin on 65 acres

The Love Nest has returned! We’re high up on the hill yet close to art and culture, great views, restaurants and dining, family-friendly activities, skiing, Bennington, Manchester VT close by. Williamstown Mass not far. A huge yard. You’ll love my place because of the coziness, the light, the comfy bed, the well equipped kitchen, privacy and views, the extreme quiet and relaxation. Waterfalls! My place is good for couples, solo adventurers, and dog guests. 420 friendly!

Guest suite in Wilmington

4.92 out of 5 average rating, 748 reviews

Architectural GuestSuite

The Guest Suite is located on the first floor of an architectural studio in historic Wilmington, Vermont. Please enjoy the piano, drums, and art supplies! The Guest Suite is both UNIVERSALLY ACCESSIBLE, TOBACCO FREE, and ANIMAL FREE due to allergies in our family. LineSync Architecture staff will be working from 8:30am - 5ish upstairs, and once in a while on the weekends. When guests are in we try to be super sensitive and quiet, but footsteps will be heard!

Cabin in Woodford

4.84 out of 5 average rating, 360 reviews

400+ Airbnb Visits: Incredible Mountain Cabin

Our cabin is off the grid, NO running water (read this twice) or indoor bathroom, but it’s comfortable and has been enjoyed by 100’s of Airbnb travelers. There is electricity, but this cabin takes an adventurer in the winter months. Winter Stays take work! Don’t be surprised of shoveling and bringing in your gear! Our reviews speak for how great rental is for people, thank you for considering a stay at our cabin.

Home in Winhall

4.98 out of 5 average rating, 364 reviews

Stunning mid-century house on 2.5 private acres

Stay at our relaxing, mid-century retreat! The house was built in the 60s but has modern amenities. A 4-wheel-drive vehicle is recommended. Our house is conveniently located 7 miles from Stratton and 12 miles from the outlets/restaurants in Manchester. Floor to ceiling windows provide a stunning view of the property. Please note, the house has a non-working fireplace.

Rental unit in Bennington

4.93 out of 5 average rating, 612 reviews

The Octopus's Garden

Welcome to the Octopus' Garden, a warm and cozy oasis located in the heart of Bennington, VT. This relaxing one bedroom suite, infused with amenities and much love, comfortably accommodates 2 people. This peaceful space is only a 10 minute walk to art, shops and dining and is the perfect hub for a variety of activities in Southern Vermont and Western Massachusetts.

Rental unit in Wilmington

4.93 out of 5 average rating, 194 reviews

Studio Apartment Sleeps 4,

Nestled in downtown Wilmington, Vt. and within walking distance 5/10 mile to downtown restaurants, pubs, boutiques, liquor store, library, chamber of commerce, atm and banks, and grocery store. Moover free shuttle to and from Mount Snow 8 miles, 10 min drive. Kitchen and full bath. Internet access, Direct TV.

Vacation rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Bennington County family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Cabin in Whitingham

4.98 out of 5 average rating, 58 reviews

Vermont Log Cabin, Lake front. Close to Mount Snow

Guest suite in Manchester

4.89 out of 5 average rating, 95 reviews

Mountain Views Solar Spa Private Retreat Suite

Chalet in Dover

4.97 out of 5 average rating, 107 reviews

Grey Wolf's Den: 5 miles to Mount Snow w/HOT TUB

Barn in Pownal

4.71 out of 5 average rating, 194 reviews

Vintage BARN Apt-POOL-HotTub-FirePit-Farms-Foliage

Home in Sunderland

Sleeps 14,Manchester,ski, hot tub,BIG views

Home in Peru

4.63 out of 5 average rating, 57 reviews

Norman Rockwell Spacious Contemporary + Hot Tub

Home in Dover

4.93 out of 5 average rating, 107 reviews

Spacious Cottage 5 mins to Mount Snow

Home in Wilmington

4.79 out of 5 average rating, 52 reviews

Chimneyhill Chalet-Pool, Full Winter Season Rental

Family- and pet-friendly home rentals

Chalet in Readsboro

4.85 out of 5 average rating, 303 reviews

The King's Cottage

Townhouse in Dorset

4.86 out of 5 average rating, 44 reviews

Green Mountain Getaway

Rental unit in Wilmington

4.93 out of 5 average rating, 180 reviews

Quaint cozy vermont apartment

Home in Mt Tabor

4.92 out of 5 average rating, 179 reviews

Now thru Dec 15th 140.00

Cabin in Readsboro

4.85 out of 5 average rating, 203 reviews

Off grid comfort cabin

Cabin in Woodford

4.98 out of 5 average rating, 145 reviews

Stone's Camp on Stamford Stream

Home in Wardsboro

4.94 out of 5 average rating, 148 reviews

Sawmill Road - between Stratton and Mount Snow

Home in Jamaica

4.86 out of 5 average rating, 277 reviews

Yellow Sweetie at the Base of Stratton

Family-friendly home rentals with a pool

Townhouse in Dover

4.96 out of 5 average rating, 143 reviews

Bear's Den - Mt Snow Townhome w/ Ski Home Trail!

Chalet in Wilmington

4.95 out of 5 average rating, 92 reviews

Rustic Sunny Vermont Home near Mount Snow

Guesthouse in Wilmington

4.96 out of 5 average rating, 24 reviews

The Inn at Quail Run- Guest House

Condo in Dover

4.87 out of 5 average rating, 228 reviews

Mt Snow Ski In/Out at Seasons

Townhouse in West Dover

4.65 out of 5 average rating, 181 reviews

MOUNT SNOW CHALET/LOFT CONDO

Home in Dover

5 out of 5 average rating, 54 reviews

The Villa - Industrial Farmhouse with Hot Tub

Townhouse in Dover

4.93 out of 5 average rating, 76 reviews

Cozy Bear- 1 mile to Mt Snow Ski Home

Home in Manchester

4.85 out of 5 average rating, 34 reviews

Your VT Ski House: Fireplace, Indoor Pool, Dogs

Destinations to explore