
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.

Adirondack Mountain Escape
Cozy up in this Adirondack escape. Upon your arrival you'll be greeted by a spacious living room, two bedrooms, a full bathroom and kitchen! Enjoy the front porch with the mountain river sounds in the background while you make dinner on the Blackstone or roast marshmallows in the fire pit. The home is minutes away from hiking trails, world class skiing, Olympic Venues, and all the Adirondack's have to offer. 45 minutes to lake Champlain, plenty of room for a boat or snowmobile trailer on site.

"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!

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.

Moon Ridge Cabin *Hottub*
Our cabin is a studio with a hot tub & all the amenities. A queen bed, linens, towels, small refrigerator/freezer, microwave, single burner cook plate, dishes, utensils, glassware, pots & pans, toaster & coffee maker. Roku Tv & dvd player with movies. The cabin's bathroom is simular to a cruise ship, you step up into your shower. There is also an private outdoor shower. There is a fire pit with an attached grill & hibachi. We have a garden area & privacy fence between our home & the cabin.

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.

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!

Riverside Tent Camping Site
Get back to nature! This is a quite riverside primitive campsite. NO BATHROOMS so everything is natural. Come let the tranquil noise of our river lul you to sleep in the fresh Adirondack mountain air. Lots of hiking, boating, rock climbing and mountain biking near by. Only 25 minutes to Lake Placid ( home of two winter Olympics) for some of the Adirondacks best restaurants and tourist destination. There are NO trash facilities on site, so if you pack it in, pack it out!

Autumn retreat w/ hot tub perfect for couples
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.

Hikers Cabin
Seasonal Cabin. Whether you are hiking, biking, climbing or paddling, Hiker's Cabin is an economical and comfortable place to stay. Private, not secluded. 1 Double bed, Outdoor shower. Screened in kitchen. Electric heater for cool nights. Charcoal grill / fire pit. No smoking indoors. No cats. Dogs allowed but must be well behaved and stay off of the furniture and bedding. Check-in @ 3 PM and beyond. Checkout at 11 AM.

Modern Tiny House
Charming oasis in the quaint Village of AuSable Forks centrally located 30 mins either to Lake Placid or Plattsburgh NY. Located 20 mins from Whiteface Mountain/15 mins to AuSable Chasm. Walking distance to town including deli, pizza place, grocery store, local pub and of course fishing on the AuSable River. Short drive to tons of hiking, boating, mountain biking and skiing and all that the Adirondacks has to offer.
Popular amenities for Chesterfield family-friendly rentals
Family-friendly home rentals with a hot tub

NEW Couples Ski Getaway Near Whiteface

Charming Private Apt in South End w/ Hot Tub

TheADKChalet w/ Hot Tub (Adirondacks)

Cozy Cabin -Top of Hill with Views

Adirondack Autumn: Unique Chalet with Hot Tub!

Lewis Brook Lodge

Woodstone Cottage an Adirondack Experience

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

Aunt Shy's Hide-Away

Secluded ADK cabin | Hike @ heart of Fall Foliage

Porcupine Farm Barn

Off-Grid ADK cabin Retreat | Unplug & Reconnect

VT Hideaway studio: breweries,hiking, dogs welcome

Bell Crest Cabin, 1 bedroom

Secluded Village Gem: Cozy Studio Overlooks River!

Beautiful lake-front cottage, Lake Champlain
Family-friendly home rentals with a pool

Upper Yurt Stay on VT Homestead

Epic Views of the Green Mountains

Luxury Alpine Studio. Ski In Ski Out. Spruce Peak

Apartment, comfy and cozy with kitchen/gas fire

Sunset Cottage on the Richelieu River CITQ#302701

Spacious Private Apartment w/ Green Mountain Views

Private Suite in the Green Mountains

Large Cozy Lodge Near Whiteface w/ Hottub & Sauna
Quick stats about holiday rentals that are family-friendly in Chesterfield
Total rentals
60 properties
Nightly prices starting at
£60 before taxes and fees
Total number of reviews
2.9K reviews
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
60 properties include access to wifi
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Mount Pocono Holiday rentals
- Quebec City Holiday rentals
- The Hamptons Holiday rentals
- Capital District, New York Holiday rentals
- Rentals with a fireplace Chesterfield
- Rentals with a kayak Chesterfield
- Pet-friendly rentals Chesterfield
- Rentals with a patio Chesterfield
- Rentals with a firepit Chesterfield
- Rentals with lake access Chesterfield
- Rentals with beach access Chesterfield
- Rentals with outdoor seating Chesterfield
- House rentals Chesterfield
- Waterfront rentals Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Family-friendly rentals Essex County
- Family-friendly rentals New York
- Family-friendly rentals United States
- Sugarbush Resort
- Parc Safari
- Bolton Valley Resort
- Whiteface Mountain Ski Resort
- Fort Ticonderoga
- Cochran's Ski Area
- Autumn Mountain Winery
- Ethan Allen Homestead Museum
- Leahy Center for Lake Champlain
- Burlington Country Club
- Country Club of Vermont
- Vermont National Country Club
- Lincoln Peak Vineyard
- Shelburne Vineyard
- Boyden Valley Winery & Spirits
- Snow Farm Vineyard & Winery
- Titus Mountain Family Ski Center
- North Branch Vineyards