
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.
FamilyKitchenGrill

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 spacesFamilyCondition

"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!
FamilyKitchenGetting around

Cozy VT Barn by Burlington-Firepit-BringUrDog-WiFi
Cozy barn, gas fireplace, fast WiFI in a peaceful wooded forest. Whether sipping coffee by the fire, spinning vinyl records or stargazing by the fire pit(wood provided), this is your space to disconnect or work remotely in comfort. Explore on-site hiking trails, snowshoe and spot wildlife. A short drive from breweries, restaurants, scenic hikes & towns. A perfect mix of seclusion & convenience, 35 mins to Burlington. Perfect for couples/solo travelers/anyone looking for a private nature escape.
KitchenIndoor spacesCondition

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.
FamilyKitchenHiking

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.
KitchenFamilyLayout

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.
KitchenFamilyHiking

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
FamilyIndoor spacesCheckout

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.
FamilyKitchenView

Private 8.5-Acres | Lux Hot Tub & EV Charger
Escape to High Peaks Hideout, a secluded 9 acre property, 10 minutes from Whiteface Mountain. This lovingly restored cabin offers a careful blend of modern comfort and rustic charm. It accommodates 4 comfortably, featuring a lofted king bed and 2 twin beds downstairs. Your mountain retreat awaits! - Luxury hot tub for 4, covered - New custom kitchen with soapstone countertops - Luxury linens - OLED TV with Sonos sound bar and Apple TV - Giant lounge sectional - Custom dimmable lighting
KitchenIndoor spacesAmenities

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 spacesLayout

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!
FamilyKitchenCheck-in
Popular amenities for Chesterfield family-friendly rentals
Family-friendly home rentals with a hot tub

Rustic Creek Cabin in ADK/Whiteface w Hot Tub
Indoor spacesKitchenCheckout

Charming getaway tucked away in the Green Mtns
KitchenFamilyGrill

Convenient Cape | Explore Burlington & Stowe
FamilyIndoor spacesBackyard

Moon Ridge Cabin *Hottub*
Indoor spacesKitchenParking

TheADKChalet w/ Hot Tub (Adirondacks)
Indoor spacesKitchenShared spaces

The Log Cabin • Hot Tub • Sauna • Swimming Hole
Indoor spacesKitchenWifi

Cozy Cabin -Top of Hill with Views
Indoor spacesKitchenWifi

Lewis Brook Lodge
Indoor spacesKitchenBiking
Family- and pet-friendly home rentals

Treehut - Secluded Treehouse in the Forest
KitchenIndoor spacesComfort

Adirondack Riverfront Retreat
Indoor spacesKitchenRiver

The Cabin @ The Birches
KitchenFamilySleep quality

The Trailhead
Indoor spacesKitchenAccess

Organic Farm Hideaway Home and Pond
KitchenFamilyHospitality

The Rustic Retreat at Twin Ponds
KitchenIndoor spacesLayout

The Carriage Barn in Historical Williston Village
Indoor spacesKitchenLocation

Ascent House | Keene
Indoor spacesFamilyLocation
Family-friendly home rentals with a pool

Cabin in the Woods VT - Discount Jay Peak Lift Tix
Indoor spacesKitchenGetting around

Luxury Alpine Studio. Ski In Ski Out. Spruce Peak
KitchenFamilyBathroom

Lower Yurt Stay on VT Homestead
KitchenIndoor spacesLong stay

Spacious Private Apartment w/ Green Mountain Views
Indoor spacesKitchenLocation

Studio Cabin near Smugglers Notch
Indoor spacesFamilyBiking

Private Suite in the Green Mountains
FamilyIndoor spacesHospitality

Cozy Lodge with Hottub/Sauna/Games near Whiteface
Indoor spacesKitchenCondition

Ski in/out Condo @ The Lodge at Spruce Peak
Indoor spacesFamilyParking
Destinations to explore
- New York Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- Quebec City Vacation rentals
- Niagara Falls Vacation rentals
- Jersey City Vacation rentals
- Portland Vacation rentals
- Newark Vacation rentals
- Mont-Tremblant Vacation rentals
- Newport Vacation rentals
- Providence Vacation rentals
- Buffalo Vacation rentals
- Waterfront rentals Chesterfield
- Rentals with lake access Chesterfield
- Rentals with a kayak Chesterfield
- House rentals Chesterfield
- Rentals with beach access Chesterfield
- Pet-friendly rentals Chesterfield
- Family-friendly rentals Essex County
- Family-friendly rentals New York
- Family-friendly rentals United States
- Sugarbush Resort
- Bolton Valley Resort
- Stowe Mountain Resort
- Fort Ticonderoga
- University of Vermont
- Middlebury College
- Lake Flower
- Lake Placid Olympic Jumping Complex K-120 Meter Jump Tower
- Snow Farm Vineyard & Winery
- Shelburne Museum
- Warren Falls
- Shelburne Vineyard
- Cold Hollow Cider Mill
- Elmore State Park
- Waterfront Park
- Boyden Valley Winery & Spirits
- Green River Reservoir State Park
- Branbury State Park
- Little River State Park
- Titus Mountain Family Ski Center
- Alburg Dunes State Park
- Niquette Bay State Park
- Sand Bar State Park
- Parc Safari





