
Family-friendly holiday 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.

The Gallery Cabin at Camp Arden
Step under a pair of moose antlers and enter a serene world without cellphone reception. Swing in a hanging log chair and have a BBQ on a screened-in porch with views of a pond. Borrow a canoe and go paddling on nearby lakes and rivers. At Camp Arden, we follow Airbnb’s and the CDC's recommended enhanced cleaning protocols. The cabin is in the Loon Lake area. It's a 20-minute drive to Saranac Lake and 35 minutes to Lake Placid. It's recommended to have your own vehicle or rental to best enjoy the Adirondacks. Because of its size taxis are expensive and an Uber may take some time to reach you. If you're flying in, the nearest airport, SLK, is 15 minutes away.

Aunt Shy's Hide-Away
Aunt Shy's hide-away is nestled on a dead end road in the Spruce Mill Brook Valley bounded by Saddle Hill and Hood Mountain (both on the 250-acre property). Situated in the Adirondack Park midway between the High Peaks and Lake Champlain (Exit 32 on I-87), this property is in an ideal base for enjoying the Adirondack Mountains and Lake Champlain Valley. Looking to get away from the daily grind, hike, bike, fish, ski, or just relax by the fire. Five minutes to the Meadowmount School of Music.

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.

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.

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. When morning comes, enjoy your coffee while cozied up in front of the fireplace. Or simply stay in bed and admire the view. With plenty of land to explore, a hike is always welcome. The choice is yours!

"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!

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.

Bright new cottage in exquisite Vermont setting
Relax in "Findaway" cottage. Centrally located between Burlington and Montpelier and directly adjacent to Sleepy Hollow cross country ski and bike area, Birds of Vermont museum and the Vermont Audubon Center. Settle in and relax, hike right out the door, or sip a drink on the deck overlooking a beaver pond where you may see beaver, otters, deer, birds or even a moose! Surrounded by gardens and not far from downhill skiing and hiking options, swimming, sailing, dining and Lake Champlain.

A-frame w/ sauna near Whiteface & Lake Placid, NY
This chalet-style cabin sits quietly in the woods with stunning, natural views and a new, private sauna. The home is in the Adirondack Park near Whiteface Mountain Ski Resort, Lake Placid, and Keene Valley, with endless opportunities for outdoor exploration & adventure year-round. Guests have access to hiking and x-country ski trails, river swimming and fishing points, and tennis courts. Enjoy the sauna, shuffleboard, record players, karaoke machine, wood stove, and fire pit at the cabin.

The Book Barn: Newly Renovated Guesthouse
Enjoy all Vermont has to offer in this bright, airy space minutes away from Burlington and the mountains. On 14 acres with a brook, it’s a short walk down a dirt road to a historic covered bridge and town common. Fall colors are breathtaking when taken in from the barn deck, while Spring and Summer visitors enjoy free concerts on the town green on Sundays. Spectacular sunsets and hot air balloons are familiar sights. It doesn’t get much more Vermonty. *Note: No Cleaning Fee!

Adirondack Cozy Log Cabin
We are a pet friendly cozy cabin set in the Jay Range. This hand-crafted log cabin was built from the trees right on the property. Featuring authentic rustic charm along with all the modern conveniences, a new cook’s kitchen, dishwasher, gas range and a wood burning stove. Relax in the deep soaking tub, perfect for after a long hike in the high peaks district. If privacy, comfort and tranquility are what you are after, the Cabin is the right place for you.

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.
Popular amenities for Chesterfield family-friendly rentals
Family-friendly home rentals with a hot tub

Woodpecker Cottage on the Lake

Convenient Cape | Explore Burlington & Stowe

Hilltop Haven

Moon Ridge Cabin *Hottub*

VanHoevenberg Ridge upper level apartment.

Cozy Cabin -Top of Hill with Views

Adirondack Winter: Unique Chalet with Hot Tub!

Guest Suite w/hot tub & fireplace
Family- and pet-friendly home rentals

Secluded ADK cabin | family fun & winter adventure

Cady’s Falls Cabin

Hydrangea House on the Hill

Water's Edge at Beaver Pond

Unique Rustic Adirondack Space

Middlebury Village Retreat | Fast Fiber WiFi

The Brookside Cabin

Adirondack Timberwolf Cabin
Family-friendly home rentals with a pool

Luxury Alpine Studio Ski in Ski out mountainside

TWO BEDROOM RENOVATED MOUNTAIN VIEW CONDO

Lower Yurt Stay on VT Homestead

Cozy two-bedroom cabin near Smugglers Notch

Spacious Private Apartment w/ Green Mountain Views

Cute two bedroom condo close to Stowe Mountain

Private Suite in the Green Mountains

Château Chavis
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Boston Holiday rentals
- Greater Toronto Area Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Pocono Mountains Holiday rentals
- Québec City Holiday rentals
- The Hamptons Holiday rentals
- Rentals with a washing machine and dryer Chesterfield
- Waterfront rentals Chesterfield
- Rentals with a firepit Chesterfield
- Rentals with lake access Chesterfield
- Rentals with beach access Chesterfield
- House rentals Chesterfield
- Rentals with a fireplace Chesterfield
- Rentals with a kayak Chesterfield
- Rentals with outdoor seating Chesterfield
- Rentals with a patio 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
- Whiteface Mountain Ski Resort
- Fort Ticonderoga
- Lake Flower
- Stowe Mountain Resort
- University of Vermont
- ECHO, Leahy Center for Lake Champlain
- Lake Placid Olympic Jumping Complex K-120 Meter Jump Tower
- Adirondak Loj
- Shelburne Museum
- Boyden Valley Winery & Spirits
- Middlebury College
- Shelburne Vineyard
- Warren Falls
- Waterfront Park
- Snow Farm Vineyard & Winery
- Lake Champlain Chocolates
- Elmore State Park
- Cold Hollow Cider Mill




