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Family-friendly vacation rentals in Windham County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Windham 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, 122 reviews

Fall Foliage in Beautiful 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, 329 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!

Farm stay in Marlboro

4.89 out of 5 average rating, 599 reviews

Carriage Barn - Marlboro

Our place is within easy reach of Mt Snow, Carinthia, Marlboro Music Festival, and the super sweet town of Brattleboro. The 2-level apartment is entirely private and self-contained. Bonus offerings include an abundance of fresh country air and proximity to miles of woods trails. It's ideal for couples, solo travelers, and it's pet-friendly too. A short walk through the woods brings you to a spring-fed lake that is quiet and pristine. Winter, spring, summer, fall. Each season has its own magic.

Home in Putney

4.94 out of 5 average rating, 365 reviews

Vermont Botanical Studio Apartment

This room is one half of a floor in our studio building (35 sq m). It is the only occupied space in the building, which is separated from the main house by a yard. There is a queen-sized bed, full bath (no-curb shower), and an outdoor shower (not available in the winter) Small kitchen with a sink, fridge, 2-burner induction hob, microwave/convection oven, toaster, coffee pot, and cookware. Arched ceiling, with ceiling fan, large windows, deck, and Maggie's botanical art lining the walls.

Cabin in Jamaica

4.89 out of 5 average rating, 364 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).

Guesthouse in Brattleboro

5 out of 5 average rating, 212 reviews

Light Filled Loft in the Vermont Countryside

Our spacious, tranquil, light-filled Barn Loft is thoughtfully and creatively designed. Complete with a living area, sleeping alcove, flat-screen TV, full kitchen, dining area, and large bathroom with a deluxe shower. A private deck with seating that looks out into our lovely Vermont woods and verdant gardens is attached to the loft. Stay a night or a week, there is plenty to do in every season. We are a friendly, welcoming, worldly, family. We look forward to hosting you at our country home.

Chalet in Dover

4.93 out of 5 average rating, 281 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.

Guesthouse in Jamaica

4.95 out of 5 average rating, 147 reviews

The Chick Inn

This is a two-story, renovated barn adjacent to the chicken coop in rural Vermont with views of the forests. It has brand new floors, a new kitchenette, and fresh look. (Some renovation is still taking place.) The chicken coop is just next door but the birds are free-range and range they will. Enjoy a private, hot shower in the garden, just outside. This listing is only suitable for people comfortable with dogs, cats, and chickens which will undoubtedly greet you outside during your stay.

Guest suite in Wilmington

4.92 out of 5 average rating, 743 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!

Rental unit in Townshend

4.93 out of 5 average rating, 214 reviews

Private Apt. on Farm, fantastic views

Self-contained apt with fantastic views, outside deck & private entrance with keypad lock. Two queen bedrooms and queen sleeping loft, kitchen and open plan living room. Located on a historic 38-acre working farm. If you need more space we have an adjoining apartment that sleeps 5. Apartment is above garage and attached to the main farmhouse. Maximum six guests.

Cabin in Brattleboro

4.88 out of 5 average rating, 472 reviews

Cottage

The "Rustic" cottage is furnished with a queen bed, sofa and dining table. There is a small deck with patio furniture, fire ring with wood supplied, and a gas barbecue. It can accommodate 2 people comfortably. Private with parking. Host in separate house. Wi Fi from Xfinity, but please note that it can be patchy. Roku TV WI FI connected to router.

Loft in Wilmington

4.93 out of 5 average rating, 185 reviews

Walk to Village/Lake Whitingham

The garage apartment is comfortable, clean and pet-friendly. Great for weekend getaways; we are just a stroll away from the lake or the village and a short drive to Mount Snow. The Moover is a local free bus to Mount Snow ski resort, Brattleboro and Bennington and is easily accessible at the traffic light.

Vacation rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Windham 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

Home in Halifax

4.87 out of 5 average rating, 46 reviews

Rural VT Retreat—Complete Privacy on 140 Acres!

Chalet in Dover

4.97 out of 5 average rating, 106 reviews

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

Cabin in Londonderry

4.82 out of 5 average rating, 432 reviews

The Honeymoon Barn - hot tub/sauna #1 Airbb S. VT

Home in Newfane

4.98 out of 5 average rating, 127 reviews

Peaceful cabin close to skiing & Brattleboro

Chalet in Jamaica

4.97 out of 5 average rating, 59 reviews

Mountain Chalet with Hot Tub

Home in Peru

4.63 out of 5 average rating, 57 reviews

Norman Rockwell Spacious Contemporary + Hot Tub

Rental unit in Londonderry

4.97 out of 5 average rating, 564 reviews

Vermont Getaway Apartment

Family- and pet-friendly home rentals

Home in Dummerston

4.99 out of 5 average rating, 334 reviews

Pinecone Pond

Rental unit in Wilmington

4.93 out of 5 average rating, 177 reviews

Quaint cozy vermont apartment

Rental unit in Town of Rockingham

4.82 out of 5 average rating, 167 reviews

Apartment on Main Street

Home in Grafton

4.97 out of 5 average rating, 143 reviews

Ephriam Bruce House- ON RIVER IN VILLAGE CENTER

Tiny home in Jamaica

4.94 out of 5 average rating, 1,199 reviews

Apple Blossom Cottage: A Tiny House

Home in Wardsboro

4.95 out of 5 average rating, 147 reviews

Sawmill Road - between Stratton and Mount Snow

Home in Guilford

4.92 out of 5 average rating, 191 reviews

Peaceful Country Home

Cabin in Jamaica

4.87 out of 5 average rating, 284 reviews

Green Mountain Modern House: iconic modern getaway

Family-friendly home rentals with a pool

Townhouse in Dover

4.96 out of 5 average rating, 142 reviews

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

Chalet in Wilmington

4.95 out of 5 average rating, 91 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, 225 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, 75 reviews

Cozy Bear- 1 mile to Mt Snow Ski Home

Condo in Dover

4.84 out of 5 average rating, 51 reviews

Mountain Therapy at Mount Snow- for all seasons

Destinations to explore