Family-friendly holiday 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 favourite
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, 348 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 favourite
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, 219 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.

Guest favourite
The living area features a cozy dark couch facing a television and electric fireplace. A coffee table with a wood-patterned surface sits on a light area rug. A small kitchenette with granite countertops is equipped with a sink, and natural light enters through a nearby window.
Flat in New North End
4.84 out of 5 average rating, 282 reviews

Bright & adorable 1 bedroom studio with parking

Welcome to our delightful space located off the ave in Burlington's New North End! You've found a gem in a quiet section of the beautiful city of Burlington. We strive to offer travelers a place to rest that promises safety and comfort. This one bedroom apartment is a convenient 7 minute drive to downtown, 1 minute drive to the beach, and only a few blocks from the bike path/lake! We are located directly on the bus line, so even travelers without a vehicle can access all Vermont has to offer.

Top guest favourite
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 favourite
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
4.99 out of 5 average rating, 202 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 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.

Top guest favourite
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.
Flat in Clintonville
4.96 out of 5 average rating, 176 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 favourite
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, 509 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 favourite
A charming cabin appears surrounded by snow-covered ground and tall trees, illuminated warmly under a night sky. The home features large windows, revealing a cozy interior with soft lighting, while snow gently rests on the roof and nearby pathways.
Cabin in Keeseville
4.93 out of 5 average rating, 138 reviews

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.

Guest favourite
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
4.85 out of 5 average rating, 151 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 favourite
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, 437 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 favourite
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, 143 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!

Top guest favourite
The Tiny Home is nestled among snow-covered trees, featuring a warm wooden exterior and a sloped roof. Soft lighting emanates from multiple windows, illuminating a welcoming entryway with a red door. Steps lead up to the porch, inviting guests inside.
Tiny home in Shelburne
4.9 out of 5 average rating, 397 reviews

Cozy Tiny House Minutes to Downtown Shelburne

220 sq. foot charming Tiny Home under tall pines with a covered porch. Great space for solo travelers and couples that like to be cozy! The rustic interior has a full kitchen, copper shower, and compost toilet. The loft bedroom is serene with 5 windows and blackout curtains (in case you want to sleep in!). Just 12 minutes to Burlington. 4 minutes to downtown Shelburne and Shelburne Museum.

Popular amenities for Chesterfield family-friendly rentals

Quick stats about holiday rentals that are family-friendly in Chesterfield

  • Total holiday rentals

    Explore 60 holiday rentals in Chesterfield

  • Nightly prices starting at

    Chesterfield holiday rentals start at $104 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,930 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    60 of Chesterfield holiday rentals include wifi 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!