
Family-friendly vacation 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.

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.

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 View Retreat
30 minutes from Lake Placid, this unique mountain-view space features a comfortable, secluded 3-room guest suite opening out to a private covered terrace showcasing unmatched views of the Adirondack Peaks. A pet-friendly space ideal for outdoor enthusiasts, a couple's getaway, those working from home, or those just looking to have a peaceful retreat in the countryside - come enjoy our 25 acres of fields, forests, ponds and private riverbank. Also available: airbnb.com/h/adkretreat

The Shepherd's Crook at Blue Pepper Farm
Tucked in the woods on our working sheep farm, our off-grid tiny house is the perfect escape and stepping stone into the Adirondack mountains for hiking, skiing, and snowshoeing. Enjoy the coziness of the Crook between forays into our north country wilderness! What you will find: adventure, peace, quiet, woodstove, candles, down blanket, fire pit, privacy, composting outhouse, firewood for sale. **Please note there is NO electricity and NO running water. Akin to glamping!

"Gateway To The Adirondacks" on Main Street
Situated in the heart of the village on Main Street in Au Sable Forks, the "Gateway to the Adirondacks", you'll find this newly renovated second floor apartment. This spacious unit offers a fully equipped kitchen, two bedrooms, full bath and comfortably furnished living room with Smart TV and WiFi. Conveniently located within walking distance to grocery stores, pub, eateries, and entertainment. Enjoy fishing, biking, hiking, Whiteface Mountain and Lake Placid.

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.

The Paddle Inn
Our house is very open and spacious. It is designed to get around easily. There are multiple places to sit and eat or enjoy nature. The house has numerous windows and is well lit. There is a lot of deck space and a big back yard for games. We are always friendly and open, just down the road if anything is needed! We love meeting new people and do what we can to make your stay comfortable!
Popular amenities for Chesterfield family-friendly rentals
Family-friendly home rentals with a hot tub

NEW Couples Ski Getaway Near Whiteface

Backyard Bunker Retreat

The Caterpillar House: Tiny w/ Hot Tub & Fire Pit

Lower Yurt Stay on VT Homestead

Sauna, Cold Plunge, Hot Tub, Paddle Boards, Bikes

Adirondack Autumn: Unique Chalet with Hot Tub!

Cozy 3 Bedroom Getaway with Hot Tub

Adirondack getaway w/trails, hot tub and sauna
Family- and pet-friendly home rentals

Aunt Shy's Hide-Away

Secluded ADK cabin | family fun & winter adventure

Porcupine Farm Barn

The cutest little cabin in the Adirondacks!

Secluded Village Gem: Cozy Studio Overlooks River!

Quiet 3 Bedroom Cottage on Lake Champlain

Walk to the Lake. Quiet neighborhood. Comfy beds.

Riverside Tent Camping Site
Family-friendly home rentals with a pool

Epic Views of the Green Mountains

Apartment, comfy and cozy with kitchen/gas fire

Spacious Private Apartment w/ Green Mountain Views

Private Suite in the Green Mountains

Cozy Lodge with Hottub/Sauna/Games near Whiteface

The Whiteface Lodge Luxury Resort & Spa - Jr Suite

Château Chavís

Serene Mountain Studio Spruce Peak Lodge | 1328
Quick stats about vacation rentals that are family-friendly in Chesterfield

Total vacation rentals
Explore 60 vacation rentals in Chesterfield

Nightly prices starting at
Chesterfield vacation rentals start at ﺩ.ﺇ294 per night before taxes and fees

Verified guest reviews
Over 2,930 verified reviews to help you choose

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
60 of Chesterfield vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chesterfield rentals

4.9 Average rating
Chesterfield stays are highly rated by guests—averaging 4.9 out of 5!
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- Sugarbush Resort
- Parc Safari
- Bolton Valley Resort
- Whiteface Mountain Ski Resort
- Fort Ticonderoga
- Cochran's Ski Area
- Autumn Mountain Winery
- Country Club of Vermont
- Ethan Allen Homestead Museum
- Burlington Country Club
- ECHO, Leahy Center for Lake Champlain
- Vermont National Country Club
- Lincoln Peak Vineyard
- Titus Mountain Family Ski Center
- Shelburne Vineyard
- Boyden Valley Winery & Spirits
- Snow Farm Vineyard & Winery
- North Branch Vineyards




