
Family-friendly holiday rentals in Chesterfield
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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.
Indoor spacesFamilyRiver

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.
KitchenFamilyCleanliness

"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!
KitchenFamilyAccess

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

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.
KitchenFamilyHiking

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.
Indoor spacesKitchenAir conditioning

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

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.
KitchenFamilyNearby

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.
KitchenFamilySleep 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.
KitchenIndoor spacesGetting around

Autumn Forest Retreat | Hot Tub + Massage Chair
⭐ TOP 1% STAY — 300+ 5★ Reviews Guests often say: “This was exactly what we needed.” Welcome to Place of Prana — a peaceful Adirondack escape designed for rest, healing, and true reset. Summer weekends are filling quickly ☀️ Book your Adirondack escape before the season is gone. Are your dates unavailable? Explore our sister stay, Place of Poiema — another peaceful Adirondack retreat designed for gathering, connection, and unforgettable time together for 10 guests.
Indoor spacesKitchenHiking

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!
Indoor spacesKitchenBeach
Popular amenities for Chesterfield family-friendly rentals
Family-friendly home rentals with a hot tub

Lodge with AC & Hot Tub
FamilyIndoor spacesBarbecue

Lewis Brook Lodge
Indoor spacesFamilySkiing

The Log Cabin • Hot Tub • Sauna • Swimming Hole
Indoor spacesKitchenHot tub

Private Beach, Bikepath Lake Cabin Hot Tub ~ UVM
Indoor spacesFamilyGetting around

Cozy Lodge with Hottub/Sauna/Games near Whiteface
KitchenFamilyQuiet

ADK Lux A-Frame Cabin w Hot Tub
Indoor spacesFamilyBathroom

Modern Hot Tub Sauna A-Frame near Whiteface
FamilyKitchenHeating

Fully Loaded - Bikes & Hot Tub - Groups Welcome!
Indoor spacesKitchenBackyard
Family- and pet-friendly home rentals

Ascent House | Keene
Indoor spacesKitchenAccess

The Cabin @ The Birches
Indoor spacesKitchenCheck-in

Adirondack Timberwolf Cabin
FamilyIndoor spacesDecor

Secluded ADK cabin | family fun & hiking adventure
FamilyKitchenSleep quality

A-frame w/ sauna near Whiteface & Lake Placid, NY
KitchenIndoor spacesGetting around

Downtown Burlington, Renovated, 1 bedroom+
FamilyKitchenGetting around

New Bridge House | 10 Minutes from Whiteface
FamilyIndoor spacesAccess

Peaceful Adirondack Cabin right on John's Brook
KitchenIndoor spacesAccess
Family-friendly home rentals with a pool

Spacious Private Apartment w/ Green Mountain Views
Indoor spacesKitchenTV

Private Suite in the Green Mountains
FamilyKitchenAccess

Le Noyan - Luxurious 6-Bedroom Getaway
KitchenFamilyLaundry

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

Stowe, Newly Renovated Topnotch Resort Townhouse
FamilyIndoor spacesWi-Fi

Cabin in the Woods VT - Discount Jay Peak Lift Tix
KitchenFamilyAccuracy

Lower Yurt Stay on VT Homestead
KitchenFamilyGetting around

Luxury Alpine Studio. Ski In Ski Out. Spruce Peak
FamilyKitchenCleanliness
Destinations to explore
- Rentals with lake access Chesterfield
- Waterfront rentals 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
- Warren Falls
- Shelburne Vineyard
- Shelburne Museum
- Cold Hollow Cider Mill
- Elmore State Park
- Waterfront Park
- Boyden Valley Winery & Spirits
- Lake Champlain Chocolates
- Green River Reservoir State Park
- Branbury State Park
- Titus Mountain Family Ski Center
- Ethan Allen Homestead Museum
- Little River State Park
- Alburg Dunes State Park
- Parc Safari





