
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!

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 w/movies. The cabin has both an inside & outside (summer)shower. We have a privacy fence between our home & cabin. In the back yard you will find hot tub, firepit & screen house. Enjoy your stay! *Also check out our off grid camping cabin The Firefly on airbnb.

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.

Quiet 3 Bedroom Cottage on Lake Champlain
You'll have a relaxing visit at this cozy, comfortable family camp. Enjoy swimming, kayaking and hiking. Explore gorgeous Lake Champlain or enjoy the view from the porch. The sunrises are spectacular! Lake Champlain is known for great year-round fishing. Tip: Bring your water shoes for maximum swimming comfort. Hop on the Essex Ferry to Vermont to experience shopping, art, restaurants and museums. The Shelburne Museum and ECHO, Leahy Center for Lake Champlain are perfect for families.

Treehouse at Bliss Ridge Farm - Best Views in VT!
This treehouse, the Birds Nest, is open May-Oct. Our “4-Season Treehouse @ Bliss Ridge,” is open year-round: https://www.airbnb.com/h/bigtreehouseatblissridgefarm — NEW SAUNA on property! Dr. Seuss-inspired tree home perched @top of 88-acre, organic hill farm, surrounded by 1000s acres of wilderness. Designed by B'fer Roth, DIY network host of The Treehouse Guys - built WITHIN living trees, not stilts! Private hiking & panoramic views of Worcester range, MR valley! No pets or animals please.

Weasley's Enchanted Treehouse @ Vermont ReTREEt
Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling for any admirer of a beloved wizarding world, or anyone who appreciates isolation in a fun space. As you cross the elevated walkways, you'll feel like you're entering a wizards treehome in the forest. The 1,100 sqft treehouse is nestled in and among trees, providing a magical and secluded escape from life. Have a question or hesitations? reach out check out our other listings for glamping style treehouses

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.

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 stay in bed and take in the views. And with plenty of woods to explore, it's your perfect escape at your pace.

Lovely Cabin on Farm with Sauna, Porch, Mtn Views
This tiny, off-grid cabin is situated on a peaceful, beautiful spot at a small, working livestock farm in the eastern Adirondacks. Your view looks west to Whiteface mountain etc. Enjoy the hum of nature from the porch that overlooks our pastures, and indulge in the small, traditional sauna and hot/cold outdoor shower that accompany your cabin. AuSable Brewery is just across the road, and Lake Champlain is just 1 mile away. Excellent local cycling, paddling, hiking, & boating abound.

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

Hilltop Haven

Lodge with AC & Hot Tub

ADK Lux A-Frame Cabin w Hot Tub

Private 8.5-Acres | Lux Hot Tub & EV Charger

The Log Cabin • Hot Tub • Sauna • Swimming Hole

Cozy Cabin -Top of Hill with Views

Adirondack Summer: Unique Chalet with Hot Tub!

Woodstone Cottage an Adirondack Experience
Family- and pet-friendly home rentals

Hill Section Carriage House

Aunt Shy's Hide-Away

Cady’s Falls Cabin

Hideaway studio: breweries, skiing, dogs welcome

Glamping VT, with touch of OZ - Bonnie Doon Manor

A-frame w/ sauna near Whiteface & Lake Placid, NY

Private Guesthouse in the heart of Vergennes

Historic Icehouse in 980 Acres Private Wilderness
Family-friendly home rentals with a pool

Cozy Bolton Valley Ski Studio • Hike & Relax

Quiet stay on 76 acres land with pool!

L'Absolut Lac Champlain, Venise-en-Québec

Lower Yurt Stay on VT Homestead

Spacious Private Apartment w/ Green Mountain Views

Sunset Cottage on the Richelieu River CITQ#302701

Cute Cottage - Poolside - Minutes To Activities

Private Suite in the Green Mountains
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 a fireplace Chesterfield
- Rentals with a kayak Chesterfield
- Rentals with a patio Chesterfield
- Rentals with a firepit Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Rentals with beach access Chesterfield
- Pet-friendly rentals Chesterfield
- Waterfront rentals Chesterfield
- Rentals with outdoor seating Chesterfield
- House rentals 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
- Middlebury College
- University of Vermont
- ECHO, Leahy Center for Lake Champlain
- Adirondak Loj
- Shelburne Museum
- Lake Placid Olympic Jumping Complex K-120 Meter Jump Tower
- Warren Falls
- Shelburne Vineyard
- Snow Farm Vineyard & Winery
- Waterfront Park
- Elmore State Park
- Cold Hollow Cider Mill





