
Family-friendly holiday rentals in Chesterfield
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Chesterfield
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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
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
"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
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
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
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
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
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
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
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
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
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 reviewsPopular amenities for Chesterfield family-friendly rentals
Family-friendly home rentals with a hot tub

Lodge with AC & Hot Tub
KitchenFamilyHot tub
4.96 out of 5 average rating, 171 reviews
Lewis Brook Lodge
Indoor spacesFamilyView
4.99 out of 5 average rating, 172 reviews
ADK Lux A-Frame Cabin w Hot Tub
FamilyIndoor spacesNearby
4.94 out of 5 average rating, 165 reviews
Secluded Chalet w/ Hottub & Stunning Mtn Views
Indoor spacesKitchenBeach
4.88 out of 5 average rating, 135 reviews
Modern Hot Tub Sauna A-Frame near Whiteface
Indoor spacesKitchenOutdoor spaces
4.98 out of 5 average rating, 185 reviews
Stylish modern lakehouse w/ Hot tub, Firepit & Gym
FamilyKitchenLocation
5.0 out of 5 average rating, 101 reviews
Huge 5 bdrm sleeps 14- Ski Hot tub Sauna fireplace
KitchenIndoor spacesOutdoor spaces
4.93 out of 5 average rating, 174 reviews
Private 8.5-Acres | Lux Hot Tub & EV Charger
Indoor spacesFamilyAccuracy
5.0 out of 5 average rating, 140 reviewsFamily- and pet-friendly home rentals

Secluded ADKcabin | family fun & Fall Foliage hike
Indoor spacesFamilyValue
4.82 out of 5 average rating, 297 reviews
Ascent House | Keene
KitchenFamilyComfort
4.98 out of 5 average rating, 250 reviews
Adirondack Timberwolf Cabin
Indoor spacesKitchenHeating
4.95 out of 5 average rating, 286 reviews
The Cabin @ The Birches
FamilyIndoor spacesValue
4.98 out of 5 average rating, 126 reviews
Amazing Lake Champlain View at Valcour Cottage
KitchenFamilyAccuracy
4.94 out of 5 average rating, 112 reviews
Adirondack Mountainside A-Frame
FamilyKitchenBiking
4.96 out of 5 average rating, 829 reviews
Secluded Village Gem: Cozy Studio Overlooks River!
Indoor spacesKitchenAccuracy
4.92 out of 5 average rating, 520 reviews
Lakefront w/ dock and sauna in the Adirondacks
FamilyKitchenView
4.93 out of 5 average rating, 123 reviewsFamily-friendly home rentals with a pool

Spacious Private Apartment w/ Green Mountain Views
KitchenIndoor spacesView
4.99 out of 5 average rating, 136 reviews
Private Suite in the Green Mountains
FamilyKitchenComfort
4.95 out of 5 average rating, 156 reviews
Private Beach, Bikepath Lake Cabin Hot Tub ~ UVM
FamilyIndoor spacesNearby
4.89 out of 5 average rating, 776 reviews
Ski In Ski Out, Chic, Fun, Cozy, Grt Location!
FamilyKitchenDecor
4.94 out of 5 average rating, 158 reviews
The Whiteface Lodge Luxury Resort & Spa - Jr Suite
KitchenFamilyBathroom
4.95 out of 5 average rating, 129 reviews
Upper Yurt Stay on VT Homestead
Indoor spacesKitchenParking
4.93 out of 5 average rating, 497 reviews
EPIC Stowe Getaway - Great For Families & Friends
Indoor spacesFamilyLayout
4.98 out of 5 average rating, 313 reviews
Gorgeous panoramic views - 4 miles to the mountain
Indoor spacesKitchenBiking
4.89 out of 5 average rating, 252 reviewsDestinations to explore
- 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
- Warren Falls
- Shelburne Vineyard
- Shelburne Museum
- Cold Hollow Cider Mill
- Elmore State Park
- Waterfront Park
- Boyden Valley Winery & Spirits
- Lake Champlain Chocolates
- Branbury State Park
- Green River Reservoir State Park
- Alburg Dunes State Park
- Little River State Park
- Titus Mountain Family Ski Center
- Ethan Allen Homestead Museum
- Parc Safari





