
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.

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.
KitchenIndoor spacesOutdoor spaces
4.93 out of 5 average rating, 383 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.
KitchenIndoor spacesOutdoor spaces
5.0 out of 5 average rating, 235 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!
FamilyKitchenAccuracy
4.97 out of 5 average rating, 118 reviews
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!
KitchenFamilyHot tub
4.98 out of 5 average rating, 280 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.
FamilyKitchenSleep quality
4.94 out of 5 average rating, 200 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 spacesWifi
4.95 out of 5 average rating, 122 reviews
Ascent House | Keene
A unique retreat meticulously crafted for resting and recharging after exploring in our beautiful Adirondack Wilderness. Flooded with natural light, every room offers calming frames of nature. Watch the sun peak through the forest and rise over the mountains through expansive windows. Ascend the levels of the house, each revealing more landscape. Experience a designer woodfired traditional Finnish sauna & totally recharge while embracing our harsh Adirondack weather. We hope you love it here.
KitchenFamilyBiking
4.98 out of 5 average rating, 250 reviews
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.
KitchenFamilyCheckout
4.83 out of 5 average rating, 236 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.
KitchenFamilyCondition
4.97 out of 5 average rating, 208 reviews
Adirondack Mountain Yurt at Blue Pepper Farm
Escape to our 30’ yurt atop a 25-acre pasture with breathtaking views of Whiteface mountain. Accommodating 2 to 6 guests, it’s perfect for family outings or adventures with friends. A winter camping experience: the yurt features basic insulation and is heated by a wood stove, with firewood for purchase on-site. Bring sleeping bags and slippers for warmth in colder temps. Embrace nature’s beauty—plan accordingly, read our reviews, and feel free to ask any questions. Your adventure awaits!
Indoor spacesFamilyHospitality
4.9 out of 5 average rating, 510 reviews
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.
KitchenIndoor spacesCleanliness
4.93 out of 5 average rating, 161 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.
Indoor spacesKitchenHospitality
4.96 out of 5 average rating, 112 reviewsPopular amenities for Chesterfield family-friendly rentals
Family-friendly home rentals with a hot tub

ADK Lux A-Frame Cabin w Hot Tub
FamilyIndoor spacesBathroom
4.94 out of 5 average rating, 165 reviews
Lewis Brook Lodge
Indoor spacesKitchenView
4.99 out of 5 average rating, 173 reviews
Cozy Lodge with Hottub/Sauna/Games near Whiteface
Indoor spacesFamilyAir conditioning
4.88 out of 5 average rating, 182 reviews
The ADK Hideout: Hot Tub, Firepit & Pure Nature
FamilyIndoor spacesGrill
4.93 out of 5 average rating, 166 reviews
Adirondack Autumn: Unique Chalet with Hot Tub!
KitchenIndoor spacesNearby
4.97 out of 5 average rating, 198 reviews
Fully Loaded - Bikes & Hot Tub - Groups Welcome!
KitchenFamilyOutdoor spaces
4.99 out of 5 average rating, 181 reviews
Private 8.5-Acres | Lux Hot Tub & EV Charger
FamilyIndoor spacesView
5.0 out of 5 average rating, 141 reviews
Modern Hot Tub Sauna A-Frame near Whiteface
KitchenIndoor spacesBiking
4.98 out of 5 average rating, 186 reviewsFamily- and pet-friendly home rentals

Adirondack Mountainside A-Frame
Indoor spacesKitchenValue
4.96 out of 5 average rating, 830 reviews
Adirondack Timberwolf Cabin
KitchenIndoor spacesHeating
4.95 out of 5 average rating, 286 reviews
Secluded ADKcabin | family fun & Fall Foliage hike
KitchenIndoor spacesAmenities
4.82 out of 5 average rating, 297 reviews
The Trailhead
Indoor spacesKitchenSleep quality
4.91 out of 5 average rating, 139 reviews
The Cabin @ The Birches
Indoor spacesKitchenOutdoor spaces
4.98 out of 5 average rating, 127 reviews
Amazing Lake Champlain View at Valcour Cottage
KitchenIndoor spacesDecor
4.94 out of 5 average rating, 112 reviews
Cozy Rustic Two Story Apartment
KitchenFamilyCheckout
4.88 out of 5 average rating, 276 reviews
Secluded Village Gem: Cozy Studio Overlooks River!
KitchenIndoor spacesOutdoor spaces
4.92 out of 5 average rating, 520 reviewsFamily-friendly home rentals with a pool

Spacious Private Apartment w/ Green Mountain Views
Indoor spacesKitchenAccuracy
4.99 out of 5 average rating, 136 reviews
Private Suite in the Green Mountains
FamilyIndoor spacesGetting around
4.95 out of 5 average rating, 156 reviews
The Brookside @ Wilmington, NY
FamilyKitchenSkiing
4.96 out of 5 average rating, 255 reviews
Private Beach, Bikepath Lake Cabin Hot Tub ~ UVM
KitchenIndoor spacesLong stay
4.89 out of 5 average rating, 776 reviews
The Whiteface Lodge Luxury Resort & Spa - Jr Suite
KitchenIndoor spacesHiking
4.95 out of 5 average rating, 129 reviews
Ski In Ski Out, Chic, Fun, Cozy, Grt Location!
KitchenFamilyCondition
4.94 out of 5 average rating, 158 reviews
Upper Yurt Stay on VT Homestead
Indoor spacesFamilyRiver
4.93 out of 5 average rating, 497 reviews
EPIC Stowe Getaway - Great For Families & Friends
KitchenFamilyWalkability
4.98 out of 5 average rating, 313 reviewsDestinations to explore
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- Sugarbush Resort
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- Fort Ticonderoga
- University of Vermont
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- Lake Flower
- Lake Placid Olympic Jumping Complex K-120 Meter Jump Tower
- Snow Farm Vineyard & Winery
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- Lake Champlain Chocolates
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