
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.

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.

"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!

Historic Icehouse in 980 Acres Private Wilderness
The Icehouse is a historic house situated in the High Peaks. The building is surrounded by a stunning private wilderness, with trails, brooks, and fields that no one but guests have access to. As the Park gets more crowded, enjoy undisturbed hiking, back-country skiing, biking, or simply going for picnics to take in some of the best views in the East! The house is very well equipped and has a great kitchen, comfy beds with high-end mattresses and linen, as well as unique furniture and artwork.

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.

4-Season Treehouse @ Bliss Ridge; Best Views in VT
Insulated, thermostat control! LUXURY! 1-of-a-kind, 5⭐️Interior bathroom, @Bliss Ridge - 88acre, OG farm, private estate surrounded by 1000s acre of wilderness. NEW SAUNA& cold plunge!!! Our 2 architectural wonders = real treehouses, built withIN the living trees, not stilted cabins. Fabulous “Jotul” fireplace, indoor hot shower / plumbing, fresh mtn spring water, stable access ramp. Our original treehouse, "The Bird’s Nest" is open May-Oct. WiFi avail at the barn! Cell svc works! No pets.

Adirondack Mountain Yurt at Blue Pepper Farm
Escape to our 30’ yurt atop a 25-acre pasture with breathtaking views of Whiteface mountain. Accommodating 2 to 6 guests, it’s perfect for family outings or adventures with friends. A winter camping experience: the yurt features basic insulation and is heated by a wood stove, with firewood for purchase on-site. Bring sleeping bags and slippers for warmth in colder temps. Embrace nature’s beauty—plan accordingly, read our reviews, and feel free to ask any questions. Your adventure awaits!

Adirondack Timberwolf Cabin
Cozy Mountain Chalet in Jay, NY on beautiful Glen Road. Only .7 miles to the Jay Covered Bridge, 3 miles to the Jay Mountain summit trail head, 7 miles to Whiteface Mountain, and 16 miles to Lake Placid. Keene and Keene Valley trail heads are only minutes away. The cabin has 3 acres of wooded property with a front driveway as well as a back access drivweway which is nice to walk. There is Satellite TV and wifi. There is good cell coverage. World Class Fishing, Ausable Rivers are close

THE VIEW! THE VIEW! THE VIEW!
A 1900 farmhouse that has been in the family for generations. Recently renovated to accommodate up to 5 guests, it is clean with simple furnishings and a SPECTACULAR VIEW! Located RIGHT ON NYS RTE 86 (close to the road) with easy access to nearby attractions. The house is split in 2 and is designed for 2 families. I rent out "The View" using airbnb exclusively. My wife and I reside in the back portion of the house with a separate entrance and separate parking.

Sunrise Lake House! Comfort-Hot Tub-Beach
Relax and recharge with family and friends at the lake! It’s the perfect place to stay year round. We aim to provide a place of comfort and relaxation with essential and fun amenities. Enjoy private lakefront access, a screened porch to relax on, kayaks and paddle boards provided in the summer. Enjoy the NEW 4 person Hot Tub with Lake views! Minutes to downtown St. Albans, offering delicious eateries and shopping at local boutiques. Burlington is 35 minutes away.

Lake Front Home in Plattsburgh - 4BR Sleeps 11!
Escape to our Lake Champlain haven! Unwind on your private rocky beach, soak in stunning lake and mountain views, and relax in our spacious, sun-filled home. Perfect for family and friends, our prime location offers easy access to local gems. Enjoy nearby City beach and Point au Roche beach. Just 10 minutes from Champlain Centre Mall for shopping. Experience lakeside living with modern comforts. Book now for an unforgettable getaway on Lake Champlain's shores!

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

Rustic Creek Cabin in ADK/Whiteface w Hot Tub

Mountain Valley Retreat

Convenient Cape | Explore Burlington & Stowe

Moon Ridge Cabin *Hottub*

TheADKChalet w/ Hot Tub (Adirondacks)

VanHoevenberg Ridge upper level apartment.

Cozy Cabin -Top of Hill with Views

Sauna, Cold Plunge, Hot Tub, Paddle Boards, Bikes
Family- and pet-friendly home rentals

Aunt Shy's Hide-Away

The Beech Retreat w/ Infrared Sauna

Adirondack Riverfront Retreat

Downtown Burlington, Renovated, 1 bedroom+

Hideaway studio: breweries, skiing, dogs welcome

Sauna, Dock & 180° Views – Lakefront Retreat

Tiny on the Hill - Sauna + Burlington + Stowe

The Brookside Cabin
Family-friendly home rentals with a pool

Slopeside Bolton Valley Studio

3rd Floor Studio @ The Lodge at Spruce Peak

Lower Yurt Stay on VT Homestead

Spacious Private Apartment w/ Green Mountain Views

Cute Cottage - Poolside - Minutes To Activities

Lux Alpine Studio Spruce Peak | 1234

Private Suite in the Green Mountains

The Whiteface Lodge Luxury Resort & Spa - Jr Suite
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
- Greater Toronto Area Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Pocono Mountains Holiday rentals
- Québec City Holiday rentals
- The Hamptons Holiday rentals
- Rentals with lake access Chesterfield
- Waterfront rentals Chesterfield
- House rentals Chesterfield
- Rentals with a fireplace Chesterfield
- Rentals with a kayak Chesterfield
- Rentals with a firepit Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Pet-friendly rentals Chesterfield
- Rentals with beach access Chesterfield
- Rentals with a patio Chesterfield
- Rentals with outdoor seating 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
- University of Vermont
- Stowe Mountain Resort
- ECHO, Leahy Center for Lake Champlain
- Adirondak Loj
- Lake Placid Olympic Jumping Complex K-120 Meter Jump Tower
- Middlebury College
- Shelburne Museum
- Boyden Valley Winery & Spirits
- Shelburne Vineyard
- Warren Falls
- Waterfront Park
- Snow Farm Vineyard & Winery
- Lake Champlain Chocolates
- Elmore State Park
- Cold Hollow Cider Mill




