
Family-friendly holiday rentals in Chesterfield
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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.

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.

Off Grid Vermont Cabin-Hike-Write
An off grid cabin in the hills of Vermont with a spectacular view of Camel's Hump. Not for everyone, (no running water, spotty cell service) but if you want quiet, beauty and solitude, this place is for you. A writer-hiker's dream. If it's chilly, the cabin's heated. There's also an ice pack (provided) fridge, propane stove, solar electricity for lights, composting toilet (no smell. Really), pots, cooking utensils, dishware etc We allow one dog (only ONE, please!) for a fee $25 per stay.

Cozy Rustic Two Story Apartment
Located on the famous Ausable River. 20 minutes to Whifeface Mountiain or Plattsburgh and the Plattsburgh Airport. 10 minutes from the AuSable Chasm. This can be your resting point after spending a fun filled day in the Adirondacks. At this location you have the opportunity to walk down to the river to fish, paint or just sit and relax in the beautiful surroundings. You’re welcome to have an evening fire in our outdoors fire pit that can be set up for beautiful scenic views of the river.

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

JUNIPER HILL cabin
Juniper Hill cabin is a new construction two bedroom/one bathroom home situated in Wilmington, NY. This cabin sits in the heart of the Adirondack mountains and is minutes to outdoor adventure of all kinds! Only five minutes to Whiteface Mountain and less than 15 minutes to downtown Lake Placid, the convenience of the location is key for both outdoor enthusiasts and those looking to just getaway and relax in nature. The Ausable River and Lake Everest are both within walking distance.

Charlotte Private Studio Apartment with a View
Welcome to our sweet inviting studio apartment. You will enjoy the quiet rural landscape, views of the Green Mountains and Mt. Philo from your bedroom. This east facing large studio offers plenty of light and open concept living. Wide pine floors and comfortable clean surrounds make this the perfect place for two adult guests or a family with children (two adults and one or two children). All are welcome. We look forward to you being our guest.

Beautiful lake-front cottage, Lake Champlain
Lakefront cottage located in Highgate Springs, Vermont, on the Canadian border. The 2-bedroom cottage sits adjacent to the owner-occupied main house, on a large one-acre lot, with 120 feet of Lake Champlain shoreline. Enjoy the stunning sunset views while sitting on the deck overlooking the water. Private dock included. Montreal and Burlington each 45 minutes away. Available level-2 car charger. Well-behaved pets allowed. Super-fast WIFI!

Aframe - Sauna, Near Lake Placid - Unique & Modern
Welcome to ADK Aframe - A luxury mid-century modern cabin! Located on a quiet road, this amazing space serves as a relaxing retreat for you to recharge after adventure filled days hiking, biking, paddling, fishing and skiing. Our pet-free home features all new furnishings and modern comforts, including a barrel sauna. The neighborhood includes private hiking/X-Country skiing trails, open space with a lake, and Ausable River access.

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

Sunrise Lake House! Comfort-Hot Tub-Beach

Moon Ridge Cabin *Hottub*

TheADKChalet w/ Hot Tub (Adirondacks)

VanHoevenberg Ridge upper level apartment.

The Log Cabin • Hot Tub • Sauna • Near Whiteface

Cozy Cabin -Top of Hill with Views

Adirondack Winter: Unique Chalet with Hot Tub!

Private ADK Tiny Home & Hot Tub for Two!
Family- and pet-friendly home rentals

Secluded ADK cabin | family fun & winter adventure

Cozy, safe, conveniently located, newly renovated.

Organic Farm Hideaway Home and Pond

The Brookside Cabin

Champlain Cottage

Secluded Village Gem: Cozy Studio Overlooks River!

The Barn in Shelburne

The Shepherd's Crook at Blue Pepper Farm
Family-friendly home rentals with a pool

Stowe, Newly Renovated Topnotch Resort Townhouse

Lower Yurt Stay on VT Homestead

Cozy two-bedroom cabin near Smugglers Notch

Spacious Private Apartment w/ Green Mountain Views

Stowe, Topnotch Resort-Best Mt & Luxury in Vermont

Private Suite in the Green Mountains

The Whiteface Lodge Luxury Resort & Spa - Jr Suite

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 fire pit Chesterfield
- House rentals Chesterfield
- Rentals with beach access Chesterfield
- Rentals with outdoor seating Chesterfield
- Rentals with a patio Chesterfield
- Waterfront rentals Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Pet-friendly rentals Chesterfield
- Rentals with a fireplace Chesterfield
- Rentals with a kayak Chesterfield
- Rentals with lake access 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
- Lake Champlain Chocolates
- Snow Farm Vineyard & Winery
- Elmore State Park
- Cold Hollow Cider Mill




