Family-friendly vacation rentals in Chesterfield

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Top-rated family-friendly rentals in Chesterfield

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
The exterior of a wooden house is displayed, featuring a sloping entrance with a wooden walkway leading to the main entry. Large windows provide views of the lake and surrounding greenery, while colorful flower beds enhance the peaceful setting.
Home in Port Kent
4.93 out of 5 average rating, 354 reviews

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.

Top guest favorite
A modern wooden exterior features a combination of large windows and a welcoming front door. The building includes two spacious garage doors, all set against a backdrop of colorful autumn foliage. A manicured pathway leads to the entrance.
Loft in Keeseville
5 out of 5 average rating, 220 reviews

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.

Top guest favorite
The entryway of a cottage is shown, featuring a green door framed by a porch light. A pumpkin rests beside a vintage milk can, while lanterns line the pathway. Plant decorations adorn the windows, providing a welcoming touch amidst the surrounding foliage.
Guesthouse in Shelburne
4.98 out of 5 average rating, 207 reviews

Cottontail Cottage - Snowshoes, Fireplace & Sauna

Quiet and peaceful cottage in a beautiful setting. Located on 6 acres adjacent to the Shelburne Pond Nature Reserve and only 15 min to the Church Street Marketplace in downtown Burlington. Enjoy the sunrise over the hills behind the cottage and sunsets over the Adirondacks to the west. Sit in the chairs or chaise lounge in the private backyard listening to the birds or relax in the shared sauna after a day of skiing or snowshoeing. (The sauna is available by reservation to ensure your privacy.)

Top guest favorite
The cabin features a charming exterior with wooden siding, a shingled roof, and decorative trim. Large windows allow natural light to fill the interior. A stack of firewood is neatly arranged beside the entrance, which is framed by vibrant landscaping.
Cabin in Au Sable Forks
4.98 out of 5 average rating, 213 reviews

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. Please use covered path on your left as you face cabin to get into back yard where you will find hot tub, firepit & screen house. Enjoy your stay!

Top guest favorite
A rustic cabin is framed by lush greenery, surrounded by a manicured garden. An outdoor picnic table is situated on the grass, complemented by a patio umbrella and flower pots. The entrance features a welcoming door, adding charm to the serene woodland setting.
Place to stay in Peru
4.93 out of 5 average rating, 174 reviews

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.

Top guest favorite
White Adirondack chairs are positioned near the river, offering a view of the flowing water and colorful autumn foliage. Trees displaying shades of orange and green line the riverbanks, creating a serene natural environment. The landscape is framed by a gently rolling background.
Apartment in Clintonville
4.96 out of 5 average rating, 181 reviews

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.

Guest favorite
A charming off-grid cabin sits amidst lush greenery, featuring wooden walls and large windows. A small porch extends from the cabin, providing an inviting space. Trees surround the area, while soft sunlight filters through the branches, creating a serene atmosphere.
Cabin in Keeseville
4.95 out of 5 average rating, 105 reviews

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.

Guest favorite
A scenic view of rolling hills and mountains is captured at sunset, with soft hues of orange and pink in the sky. In the foreground, sheep graze peacefully on vibrant green grass, framed by a rustic structure and a hint of electrified fence.
Tiny home in Jay
4.94 out of 5 average rating, 518 reviews

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!

Top guest favorite
Cabin in Keeseville
4.93 out of 5 average rating, 143 reviews

Winter Wonderland 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.

Guest favorite
An exterior view of a charming tiny home surrounded by vibrant autumn foliage. A lush lawn covered in fallen leaves leads to a white picket fence and a welcoming entryway. Bright yellow mums are positioned near the porch, enhancing the inviting atmosphere of the property.
Tiny home in Au Sable Forks
4.86 out of 5 average rating, 155 reviews

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.

Top guest favorite
A charming cabin is set within a wooded landscape, surrounded by lush greenery. The dark exterior is complemented by green shutters and a small garden in front. A second structure is visible behind the cabin, with a porch that offers a casual outdoor space.
Cabin in Schuyler Falls
4.89 out of 5 average rating, 441 reviews

Cozy Cabin

Cabin located across from Macomb State Park providing access to cross country skiing. 30 minute drive to Whiteface Mt. Ski Area. Sleeps 4 with 2 twins and a double in upstairs loft. Fully furnished kitchen, bath with shower. Quiet space. 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.

Guest favorite
An outdoor dining area is featured, with a circular glass table surrounded by four rattan chairs, each adorned with teal cushions. The space is softly illuminated by warm lights, highlighting the side of the house with multiple large windows.
Home in Keeseville
4.85 out of 5 average rating, 145 reviews

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