Family-friendly vacation rentals in Chesterfield

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Chesterfield

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

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Top guest favorite

The exterior of a wooden house is displayed, featuring a sloping entrance with a wooden walkway leading to the main entry. Large windows provide views of the lake and surrounding greenery, while colorful flower beds enhance the peaceful setting.

Home in Port Kent

4.93 out of 5 average rating, 377 reviews

18 Lake Stunning View of Champlain in Adirondacks

Welcome to 18 Lake. Situated in beautiful, quiet, Port Kent, NY, this gem is the perfect place to relax and get away. People come from all across the country to tour this charming area on bicycles in summer, and from all over the world during the winter for Lake Placid's winter sports. In fall, the colors are vibrant and breathtaking. Fresh maple products are on tap in Spring. Enjoy area attractions such as Ausable Chasm, High Falls Gorge, Port Kent Beach, golf, orchards, hiking and biking.

FamilyIndoor spacesQuiet

Top guest favorite

A modern wooden exterior features a combination of large windows and a welcoming front door. The building includes two spacious garage doors, all set against a backdrop of colorful autumn foliage. A manicured pathway leads to the entrance.

Loft in Keeseville

5 out of 5 average rating, 230 reviews

Adirondack Gem in the Champlain Valley/VT Views

Our country home is nestled in a peaceful wooded area overlooking Lake Champlain and the VT Green Mtns . The 900 sq ft Loft is private and welcoming, with many thoughtful details for your comfort and total relaxation. Cuddle up with comfy chairs, cozy throws and an abundance of books and magazines. It is so quiet, and the beds so comfortable, that a restful night's sleep is almost a guarantee. Kayaking, canoeing, and fishing opportunities abound with water access close-by. Very kid-friendly.

Indoor spacesKitchenGrill

Top guest favorite

A cottage is seen perched on a grassy bank, overlooking a river. Tall trees frame the scene, providing a natural backdrop. The water's surface reflects the surroundings, while a hint of light is visible from the cottage window, suggesting warmth inside.

Home in Willsboro

4.97 out of 5 average rating, 118 reviews

"Beau Overlook" Enjoy 2 states from 1 great spot!

Come enjoy LOGISTICS to the Green Mountains of VT & the heart of the DACKS in one sweet spot. "Beau Overlook Cottage" perched high on the banks of the BOQUET RIVER, with sweet sounds of water tumbling over river rocks below. This home is situated 2 miles north of the Lake Champlain ~ Boquet River Delta. The beautiful LAKE scene at the sandbar of the delta must be seen to be appreciated. This relaxing sanctuary will provide an upscale and sophisticated home, whose logistics cannot be beat!

KitchenIndoor spacesSkiing

Superhost

A grassy area features two lounge chairs positioned to overlook the Au Sable River, with a small red table nearby. Lush green trees border the riverbanks, and stacked firewood is visible to the left, creating a serene outdoor setting.

Apartment in Au Sable Forks

4.82 out of 5 average rating, 216 reviews

Gateway to the Adirondacks on the River “The East”

Situated directly on the Au Sable River, where the West and East branch meet, you'll find this comfortable duplex, located in Au Sable Forks, the "Gateway to the Adirondacks". The "East" offers a fully equipped kitchen, two bedrooms, full bath and comfortably furnished living room and Wi-Fi. Conveniently located within walking distance to grocery stores, pub, eateries and entertainment. Enjoy fishing, biking, hiking, Whiteface Mountain and Lake Placid. Come stay and enjoy the Adirondacks.

KitchenIndoor spacesHeating

Top guest favorite

Place to stay in Peru

4.93 out of 5 average rating, 189 reviews

The Brookside Cabin

Our Cabin is nestled in the woods of the Adirondack Mountains. The Cabin is behind our family home. We are on a country road close to two towns. Our area offers many amenities such as fishing, hiking, boating, golf, hunting , wine tasting, leaf peeping. The cabin is heated by a wood stove and is the only heat source. “Wood Stove will injure a small child. Fast moving water in brook. Children 7 and up is ok with pre approval. The outside shower is heated, hot water available mid April -Nov.

FamilyKitchenWifi

Top guest favorite

Sunlight filters through tall trees, casting elongated shadows on a grassy area by the lake. The serene water reflects the sky, creating a peaceful atmosphere. A few chairs are positioned on the grass, inviting relaxation and enjoyment of the picturesque surroundings.

Home in Willsboro

4.95 out of 5 average rating, 117 reviews

Quiet 3 Bedroom Cottage on Lake Champlain

You'll have a relaxing visit at this cozy, comfortable family camp. Enjoy swimming, kayaking and hiking. Explore gorgeous Lake Champlain or enjoy the view from the porch. The sunrises are spectacular! Lake Champlain is known for great year-round fishing. Tip: Bring your water shoes for maximum swimming comfort. Hop on the Essex Ferry to Vermont to experience shopping, art, restaurants and museums. The Shelburne Museum and ECHO, Leahy Center for Lake Champlain are perfect for families.

FamilyIndoor spacesSleep quality

Top guest favorite

A charming treehouse is nestled among lush green trees, featuring large windows that glow warmly at dusk. A connecting bridge is illuminated with string lights, creating a welcoming pathway. Ferns and forest foliage add to the natural surroundings, enhancing the serene woodland atmosphere.

Treehouse in Moretown

4.97 out of 5 average rating, 191 reviews

Treehouse at Bliss Ridge Farm - Best Views in VT!

This treehouse, the Birds Nest, is open May-Oct. Our “4-Season Treehouse @ Bliss Ridge,” is open year-round: https://www.airbnb.com/h/bigtreehouseatblissridgefarm — NEW SAUNA on property! Dr. Seuss-inspired tree home perched @top of 88-acre, organic hill farm, surrounded by 1000s acres of wilderness. Designed by B'fer Roth, DIY network host of The Treehouse Guys - built WITHIN living trees, not stilts! Private hiking & panoramic views of Worcester range, MR valley! No pets or animals please.

Indoor spacesKitchenBiking

Guest favorite

A unique treehouse is seen perched among tall trees, with a blend of rustic wood siding and large windows that reflect the surrounding greenery. The structure stands elevated from the ground, supported by slender pillars, blending harmoniously with the natural forest environment.

Treehouse in Hancock

4.98 out of 5 average rating, 176 reviews

Weasley's Enchanted Treehouse @ Vermont ReTREEt

Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling for any admirer of a beloved wizarding world, or anyone who appreciates isolation in a fun space. As you cross the elevated walkways, you'll feel like you're entering a wizards treehome in the forest. The 1,100 sqft treehouse is nestled in and among trees, providing a magical and secluded escape from life. Have a question or hesitations? reach out check out our other listings for glamping style treehouses

Indoor spacesKitchenGetting around

Top guest favorite

White Adirondack chairs are positioned near the river, offering a view of the flowing water and colorful autumn foliage. Trees displaying shades of orange and green line the riverbanks, creating a serene natural environment. The landscape is framed by a gently rolling background.

Apartment in Clintonville

4.96 out of 5 average rating, 188 reviews

Cozy Rustic Apartment

We are located on the famous Ausable River within a 30 minute drive to many of the High Peak trails, the beautiful Ausable Chasm, and Whiteface mountain. We are 5 miles from Interstate 87. The apartment can be a cozy retreat after spending a day exploring in the Adirondacks. Spend time strolling down to the river to enjoy the scenic views or enjoy quality downtime with family. The apartment has a unique style of its own that will provide you a comfortable and reasonable price place to stay.

KitchenIndoor spacesCleanliness

Guest favorite

A charming off-grid cabin sits amidst lush greenery, featuring wooden walls and large windows. A small porch extends from the cabin, providing an inviting space. Trees surround the area, while soft sunlight filters through the branches, creating a serene atmosphere.

Cabin in Keeseville

4.95 out of 5 average rating, 108 reviews

Lovely Cabin on Farm with Sauna, Porch, Mtn Views

This tiny, off-grid cabin is situated on a peaceful, beautiful spot at a small, working livestock farm in the eastern Adirondacks. Your view looks west to Whiteface mountain etc. Enjoy the hum of nature from the porch that overlooks our pastures, and indulge in the small, traditional sauna and hot/cold outdoor shower that accompany your cabin. AuSable Brewery is just across the road, and Lake Champlain is just 1 mile away. Excellent local cycling, paddling, hiking, & boating abound.

KitchenIndoor spacesCheck-in

Guest favorite

A welcoming interior of the tiny house features natural wood beams and a cozy sleeping area elevated on a wooden platform. A patterned area rug adds texture, while large windows allow daylight to illuminate the space. Decorative elements include framed butterfly art and greenery.

Tiny home in Burlington

4.89 out of 5 average rating, 200 reviews

Tiny House & Sauna in Burlington

Adorable one room tiny house 5 minutes from Downtown and beaches on Lake Champlain. Located in the New North End of Burlington, this urban get away in a quiet residential neighborhood features the Burlington Bike Path down the street, a vegan cafe across the road and use of spacious backyard sauna. Guests have access to a private bathroom through a separate entry in the main house, about 20 steps away. Breakfast nook includes coffee, tea, microwave, mini fridge & sink.

FamilyIndoor spacesWalkability

Top guest favorite

An outdoor courtyard features a salt-water hot tub and natural wooden seating. Lush greenery envelops the space, creating an intimate feel. A rustic barrel-shaped structure adds a unique element to the design. The ground is covered in smooth gravel, enhancing the serene atmosphere.

Guest suite in Burlington

4.98 out of 5 average rating, 272 reviews

Sauna, Cold Plunge, Hot Tub, Paddle Boards, Bikes

*Burlington’s 1st Spa + Stay. Recently renovated and upgraded! We added a sauna, a cold plunge, upgraded bicycles, enlarged the courtyard, added an exercise/yoga room, robes and sandals, an espresso machine… the list goes on! New photos were just added! We still have a king bed, a queen bed, and the two twins that make up the Dream Sofa in the living room. Pets are still welcome! We have new stuff for kids too! We’re right near the beach and bike path!

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