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Family-friendly vacation rentals in Wilmington

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Wilmington

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! ☺

Guesthouse in Brattleboro

4.99 out of 5 average rating, 218 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.

Home in Wilmington

4.83 out of 5 average rating, 162 reviews

The Vermont Barn (Mount Snow)

Follow/Tag us on Instagram: thevermontbarn Perfect place to kick back after a long day of hiking, skiing or even just the hustle and bustle of everyday life any time of year! Enjoy our wood stove or soak in the hot tub outside. Our place is very accessible to: hiking, skiing, (Mt. Snow), kayaking, fishing, lake, biking, golfing and small town gems just down the road. Full access to Clubhouse (5 min walk): pools, hot tub, arcade and gym. Great for families, large groups, kid and pet friendly.

Rental unit in Shelburne Falls

4.97 out of 5 average rating, 523 reviews

In town, newly renovated studio with private deck

Come explore our unique area and stay in a renovated, light filled studio with private entrance, secluded deck , kitchenette and bath located in the quaint New England village of Shelburne Falls.We are within easy walking distance to numerous shops, candlepin bowling, Glacial potholes, tennis/basketball courts, Bridge of Flowers, eateries/restaurants, Pothole pictures, groceries, playgrounds, hiking & swimming areas, a natural food store and art galleries.Close to Berkshire East and Zoar!

Chalet in Dover

4.92 out of 5 average rating, 288 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.

Home in Wilmington

4.91 out of 5 average rating, 139 reviews

Martin Ski Barn - 4BR Ski House, 15 min to Mt Snow

15 min to Mount Snow, 35 to Stratton! Come enjoy our 4 bedroom, 2 bathroom home in the charming Chimney Hill area of Wilmington, VT. This home is a perfect getaway for those looking for easy living, rest, relaxation, and family fun. The house has 4 bedrooms and comfortably sleeps 8 adults. Master bedroom has a King bed, and there is one Queen room, one Full room with a twin trundle, and one room with two Twin beds. There is also a pack n’ play available for use.

Guest suite in Wilmington

4.92 out of 5 average rating, 751 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 Bennington

4.93 out of 5 average rating, 620 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.

Cabin in Wilmington

4.93 out of 5 average rating, 441 reviews

Picturesque Cabin near Mt Snow

Enjoy fall in Vermont! Our cabin is the perfect spot to experience cozy VT charm without missing out on modern amenities. The beautiful Green Mountains are right outside our door as well as nearby lakes and rivers. The cabin is well equipped with 3 bedrooms, 1 bath; and you'll love the screened-in porch out back. We’re also dog-friendly!

Rental unit in Wilmington

4.93 out of 5 average rating, 181 reviews

Quaint cozy vermont apartment

My place is close to parks, great views, restaurants and dining, art and culture. You’ll love my place because of privacy the sky lights, high ceiling, the comfy bed, the kitchen, the neighborhood, and the outdoors space. My place is good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets).

Rental unit in Wilmington

4.92 out of 5 average rating, 195 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.

Tiny home in Jamaica

4.94 out of 5 average rating, 1,213 reviews

Apple Blossom Cottage: A Tiny House

The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Popular amenities for Wilmington family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Home in Colrain

4.93 out of 5 average rating, 167 reviews

Secluded Farmhouse Retreat - stunning views

Home in Hancock

4.86 out of 5 average rating, 44 reviews

Jiminy Peak Peaceful Home in Berkshires

Cottage in Shaftsbury

4.98 out of 5 average rating, 641 reviews

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

Cabin in Londonderry

4.82 out of 5 average rating, 446 reviews

Stunning Rustic Apple Barn - hot tub & sauna

Condo in Dover

4.84 out of 5 average rating, 51 reviews

Mountain Therapy at Mount Snow- for all seasons

Home in Newfane

4.98 out of 5 average rating, 130 reviews

Peaceful cabin close to skiing & Brattleboro

Rental unit in Londonderry

4.96 out of 5 average rating, 568 reviews

Vermont Getaway Apartment

Rental unit in West Townshend

4.91 out of 5 average rating, 327 reviews

Private Apt on Farm, Hot Tub with views!

Family- and pet-friendly home rentals

Guesthouse in Stephentown

5 out of 5 average rating, 394 reviews

Dog Friendly Studio

Cabin in Shaftsbury

4.9 out of 5 average rating, 400 reviews

The LoveNest -Charming private cabin on 65 acres

Home in Dummerston

4.99 out of 5 average rating, 338 reviews

Pinecone Pond

Rental unit in Town of Rockingham

4.82 out of 5 average rating, 172 reviews

Apartment on Main Street

Home in Williamstown

4.82 out of 5 average rating, 187 reviews

Walking distance to downtown

Cabin in Readsboro

4.85 out of 5 average rating, 205 reviews

Off grid comfort cabin

Cabin in Pawlet

4.93 out of 5 average rating, 138 reviews

Hickory Ridge, Vermont Log Cabin, no cleaning fee

Home in Wardsboro

4.94 out of 5 average rating, 148 reviews

Sawmill Road - between Stratton and Mount Snow

Family-friendly home rentals with a pool

Home in Salem

4.98 out of 5 average rating, 185 reviews

Magical Farm Getaway - a must visit!

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

Quick stats about vacation rentals that are family-friendly in Wilmington

Total rentals
260 properties
Nightly prices starting at
$90 before taxes and fees
Total number of reviews
9.6K reviews
Pet-friendly rentals
110 properties allow pets
Rentals with a pool
60 properties have a pool
Rentals with dedicated workspaces
130 properties have a dedicated workspace

Destinations to explore