Family-friendly holiday 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 favourite
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

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.

FamilyKitchenAccuracy

4.93 out of 5 average rating, 383 reviews
Top guest favourite
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

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.

FamilyIndoor spacesGetting around

5.0 out of 5 average rating, 235 reviews
Guest favourite
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

"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!

FamilyIndoor spacesCheck-in

4.97 out of 5 average rating, 118 reviews
Top guest favourite
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

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

*New art! It hasn’t been photographed but it’s on the walls! Burlington’s 1st Spa + Stay. Recently renovated and upgraded! A sauna, cold plunge, 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!

KitchenFamilyAccuracy

4.98 out of 5 average rating, 279 reviews
Top guest favourite
Place to stay in Peru

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

4.93 out of 5 average rating, 199 reviews
Top guest favourite
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

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.

Indoor spacesKitchenDecor

4.95 out of 5 average rating, 122 reviews
Top guest favourite
Home in Au Sable Forks

Adirondack Vacation Destination Lodge on Fern Lake

This mountain retreat is designed for relaxation, comfort and fun! Located in the pristine Adirondack Park and located adjacent to Palmer Brook Sportsman Club that provides over 5000+ acres of recreational trails for xc skiing (no lifts/ tow rope), snowshoe, snowmobile, atv, mountain bike trails all starting from your doorstep. Arrangements can be made for access Jan-Aug months simply include this request in your stay and enjoy the great outdoors all day and relax by the fireplace at night.

FamilyIndoor spacesTV

4.83 out of 5 average rating, 236 reviews
Top guest favourite
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

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.

FamilyIndoor spacesDecor

4.97 out of 5 average rating, 208 reviews
Top guest favourite
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.
Flat in Clintonville

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.

Indoor spacesFamilyHospitality

4.96 out of 5 average rating, 196 reviews
Top guest favourite
The front of the cabin is framed by lush greenery and features a welcoming red door. Around a cozy patio area, four classic Adirondack chairs are arranged, complemented by blooming flower pots offering vibrant colors.
Cabin in Keeseville

Adirondack Cabin Retreat – Hot Tub + Lake

Plan a peaceful stay for up to 5 people in this cozy, well-appointed cabin with lake access that marries rustic charm with modern amenities. This is a vintage Adirondack retreat with access to a quiet and private lake perfect for swimming, paddling and fishing. We have loons and a resident bald eagle. A local winery and brewery are so close by too! Ausable Chasm is fun family-friendly attraction just down the road. Lastly for security, we have a camera focused on driveway entrance.

FamilyKitchenAccess

4.93 out of 5 average rating, 161 reviews
Guest favourite
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

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.

Indoor spacesKitchenHeating

4.96 out of 5 average rating, 112 reviews
Top guest favourite
Cabin in Upper Jay

Log Cabin • 10 Min to Whiteface • Hot Tub • Sauna

Perfect for couples & large groups! Cozy cabin + outbuildings. 10 minutes to the ski resort, on-site swimming hole & fishing access, cedar hot tub & sauna, foosball, hiking, walkable restaurants, level 2 EV charger, boutique furnishings. The Log Cabin at Warner’s Camp is a piece of art. This property consists of a bespoke 3 bed, 2 bath log cabin, a studio cabin with additional bed and bath, plus an extra sleeper cabin (a charming enclosed lean-to, overlooking a stream).

FamilyIndoor spacesHot tub

4.99 out of 5 average rating, 136 reviews

Popular amenities for Chesterfield family-friendly rentals

Family-friendly home rentals with a pool

Top guest favourite
A vibrant garden surrounds a pool area, featuring blooming tulips and a variety of colorful flowers. A patio umbrella provides shade over seating near the pool, with scenic views of rolling hills and distant mountains visible in the background.
Flat in Monkton

Spacious Private Apartment w/ Green Mountain Views

KitchenIndoor spacesView

4.99 out of 5 average rating, 136 reviews
Top guest favourite
A bright and spacious loft area is highlighted by tall windows allowing natural light to illuminate the room. A well-equipped kitchenette is visible, along with a cozy seating arrangement featuring a small table and two chairs, next to a large bed dressed in soft linens.
Guest suite in Starksboro

Private Suite in the Green Mountains

FamilyKitchenComfort

4.95 out of 5 average rating, 156 reviews
Guest favourite
Flat in Burlington

Private Beach, Bikepath Lake Cabin Hot Tub ~ UVM

FamilyIndoor spacesNearby

4.89 out of 5 average rating, 776 reviews
Guest favourite
A cozy living area features a built-in conversation pit surrounding a modern fireplace. Natural light streams in from large windows, illuminating comfortable seating adorned with colorful cushions. Wooden bookshelves filled with books create a warm and inviting backdrop.
Townhouse in Stowe

Ski In Ski Out, Chic, Fun, Cozy, Grt Location!

FamilyKitchenDecor

4.94 out of 5 average rating, 158 reviews
Top guest favourite
The exterior of a large lodge features a blend of stone and timber construction, characterized by multiple expansive windows. A covered entrance area showcases wooden beams and a decorative chandelier. Surrounding landscaping includes green grass, shrubs, and flowering plants, enhancing the lodge's natural setting.
Serviced apartment in Lake Placid

The Whiteface Lodge Luxury Resort & Spa - Jr Suite

KitchenFamilyBathroom

4.95 out of 5 average rating, 129 reviews
Guest favourite
A cozy yurt is partially obscured by lush greenery, suggesting a tranquil, natural setting. A wooden structure supports a canvas cover nearby, with a table and chairs visible, inviting outdoor dining. Sunlight filters through the trees, enhancing the peaceful atmosphere.
Yurt in Randolph

Upper Yurt Stay on VT Homestead

Indoor spacesKitchenParking

4.93 out of 5 average rating, 497 reviews
Top guest favourite
A spacious two-story home is set among lush greenery, with a large front deck featuring white railings. The exterior showcases a mix of light-colored siding and dark shutters, while tall trees provide a natural backdrop, creating a peaceful atmosphere.
Home in Stowe

EPIC Stowe Getaway - Great For Families & Friends

Indoor spacesFamilyLayout

4.98 out of 5 average rating, 313 reviews
Top guest favourite
A spacious living room features a large brown leather sofa with decorative pillows, accompanied by two armchairs. A wooden coffee table sits on an oriental-style rug, and a couple of framed artworks adorn the walls. Floor-to-ceiling windows provide an airy atmosphere.
Townhouse in Stowe

Gorgeous panoramic views - 4 miles to the mountain

Indoor spacesKitchenBiking

4.89 out of 5 average rating, 252 reviews