
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.
FamilyKitchenCondition

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 spacesFamilyRiver

"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 spacesTV

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.
FamilyKitchenLong stay

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 spacesKitchenValue

The Rustic Retreat at Twin Ponds
Take it easy and make yourself right at home in our woodsy cabin tucked away in the Cold Hollow Mountains. As you head down the drive, let your worries fade away. You’re now on cabin time. Relax in the clawfoot tub after a day of travel or prepare a home-cooked meal in the well equipped kitchen. Wake up to coffee on the deck or take a stroll around the pond. And you won’t regret kicking back in the evenings - star gazing is simply magical! We are certain that you‘ll have a hard time leaving!
KitchenIndoor spacesSkiing

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 spacesKitchenSkiing

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 spacesLaundry

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.
Indoor spacesKitchenSleep quality

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 spacesKitchenLayout

The Roost - Recharge & Relax
Enjoy being immersed in nature when you stay in this unique treehouse to unwind while experiencing some of the best sights and nature in Vermont. This cabin up on stilts and bordering one of Vermont's beautiful state parks. Views of the walkable Waterbury reservoir can be seen from its perch in the trees. "The Roost" aims for a balance of rustic meets elegance. With a tiled shower and heated flooring through out- one can truly reconnect and recharge in this unique experience.
Indoor spacesFamilyBeach

The Berghüttli: Glowing Swiss Hut in the Forest
The Berghüttli ("little mountain hut") is a Swiss-inspired hut and farm stay surrounded by National Forest in Goshen, VT (pop. 168). A completely private escape—no other structures in sight, just woods and quiet. Inside, a wall of windows brings the forest right up to you, while glowing maple plywood fills the space with warm light. High-speed fiber internet runs a reliable 300 Mbps. Stay connected or switch off completely. Search "The Berghüttli" on YouTube for a video tour.
KitchenIndoor spacesTV
Popular amenities for Chesterfield family-friendly rentals
Family-friendly home rentals with a hot tub

Rustic Creek Cabin in ADK/Whiteface w Hot Tub
KitchenIndoor spacesHospitality

So. Burl. quiet setting 10 mins fr. everything
KitchenIndoor spacesSkiing

Lodge with AC & Hot Tub
FamilyKitchenRiver

A-Frame | Hot Tub | Dog Friendly | Fenced Yard
FamilyKitchenOutdoor spaces

Private 8.5-Acres | Lux Hot Tub & EV Charger
FamilyIndoor spacesCleanliness

The Log Cabin • Hot Tub • Sauna • Swimming Hole
FamilyIndoor spacesTV

Lewis Brook Lodge
FamilyKitchenHospitality

Woodstone Cottage an Adirondack Experience
KitchenFamilyTV
Family- and pet-friendly home rentals

Cozy VT Barn by Burlington-Firepit-BringUrDog-WiFi
FamilyKitchenView

Adirondack Riverfront Retreat
Indoor spacesKitchenRiver

Cady’s Falls Cabin
KitchenIndoor spacesHeating

The Cabin @ The Birches
KitchenIndoor spacesWalkability

Adirondack Timberwolf Cabin
FamilyIndoor spacesLayout

TheADKChalet w/ Hot Tub (Adirondacks)
Indoor spacesFamilyLayout

A-frame w/ sauna near Whiteface & Lake Placid, NY
FamilyIndoor spacesCheck-in

Adirondack Cozy Log Cabin
FamilyKitchenSleep quality
Family-friendly home rentals with a pool

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

Lower Yurt Stay on VT Homestead
KitchenIndoor spacesDecor

Spacious Private Apartment w/ Green Mountain Views
KitchenIndoor spacesBeach

Gorgeous panoramic views - 4 miles to the mountain
FamilyIndoor spacesTV

Private Suite in the Green Mountains
FamilyKitchenCondition

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

Château Chavis
Indoor spacesKitchenBackyard

Le Noyan - Luxurious 6-Bedroom Getaway
KitchenIndoor spacesAccess
Destinations to explore
- New York Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- Quebec City Vacation rentals
- Niagara Falls Vacation rentals
- Portland Vacation rentals
- Jersey City Vacation rentals
- Newark Vacation rentals
- Mont-Tremblant Vacation rentals
- Newport Vacation rentals
- Providence Vacation rentals
- Bar Harbor 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
- ECHO, Leahy Center for Lake Champlain
- Snow Farm Vineyard & Winery
- Shelburne Museum
- Warren Falls
- Shelburne Vineyard
- Cold Hollow Cider Mill
- Elmore State Park
- Waterfront Park
- Boyden Valley Winery & Spirits
- Lake Champlain Chocolates
- Green River Reservoir State Park
- Branbury State Park
- Ethan Allen Homestead Museum
- Titus Mountain Family Ski Center
- Little River State Park
- Alburg Dunes State Park





