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.

0 of 0 items showing

1 of 3 pages

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, 335 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, 213 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

A well-appointed kitchen and dining area is showcased. A wooden table with four chairs is situated beneath a chandelier. Dark appliances stand beside wooden cupboards, while a large window allows natural light to fill the space. The floor features rustic tiles, enhancing the cozy ambiance.

Apartment in Au Sable Forks

4.94 out of 5 average rating, 115 reviews

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.

Superhost

Two red Adirondack chairs are positioned on a grassy area, facing a gently flowing river. Lush green trees and shrubs surround the landscape, creating a serene environment. A stone fire pit is located nearby, adding to the outdoor charm.

Apartment in Au Sable Forks

4.87 out of 5 average rating, 267 reviews

Gateway to the Adirondacks on the River “The West”

Situated directly on the Au Sable River, where the West and the East branch meet, you'll find this comfortable duplex, located in Au Sable Forks, the "Gateway to the Adirondacks". The West offers a fully equipped kitchen, three bedrooms, full bath, and comfortably furnished living room and Wi-Fi. Conveniently located within walking distance to grocery stores, pub, eateries, and entertainment. Enjoy fishing, biking, hiking, Whiteface mountain and Lake Placid. Come stay and enjoy the Adirondacks

Guest favorite

The exterior of the chalet is shown, featuring a spacious wooden deck with several red chairs. Lush greenery and vibrant flowers add color to the scene. Large windows provide views of the surrounding landscape, enhancing the cozy architecture of the home.

Cottage in Keeseville

4.91 out of 5 average rating, 100 reviews

Lakefront Adirondack, private beach❤ +kayaks, Wifi

Our family cottage around Lake Champlain offers the best view you can find in the area! Direct access to the lake with a private beach, a large dock, 2 kayaks and a large garden. The water is crystal clear and the view on the Green Mountains is breath taking. The area is full of nearby things to do: Adirondack Park, Ausable Chasm, White Face Mountain, Lake Placid, Plattsburgh, Burlington, small brewery and winery. The living space is located on the 2nd floor, with a play room on the 1st floor.

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

4.92 out of 5 average rating, 159 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.

Guest favorite

Two white Adirondack chairs are positioned on a grassy area overlooking the Ausable River. The river flows gently under a cloudy sky, surrounded by trees displaying vibrant autumn foliage in shades of orange and green.

Apartment in Clintonville

4.87 out of 5 average rating, 252 reviews

Cozy Rustic Two Story Apartment

Located on the famous Ausable River. 20 minutes to Whifeface Mountiain or Plattsburgh and the Plattsburgh Airport. 10 minutes from the AuSable Chasm. This can be your resting point after spending a fun filled day in the Adirondacks. At this location you have the opportunity to walk down to the river to fish, paint or just sit and relax in the beautiful surroundings. You’re welcome to have an evening fire in our outdoors fire pit that can be set up for beautiful scenic views of the river.

Guest favorite

A charming treehouse is nestled among lush green trees, featuring large windows that glow warmly at dusk. A connecting bridge is illuminated with string lights, creating a welcoming pathway. Ferns and forest foliage add to the natural surroundings, enhancing the serene woodland atmosphere.

Treehouse in Moretown

4.96 out of 5 average rating, 161 reviews

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 - an authentic treehouse built WITHIN living trees, not stilts! Private hiking & panoramic views of Worcester range, MR valley!

Top guest favorite

An exterior view of a two-story apartment building is presented, featuring a light-colored siding and brick accents. A wide, paved driveway leads to the front entrance, bordered by a landscaped area with green shrubs. Trees provide shade, and the setting appears peaceful.

Apartment in Plattsburgh

4.96 out of 5 average rating, 180 reviews

full 2 bedroom apt unit

This spacious two bedroom apartment is centrally located near all major restaurants, shopping and top notch local eateries. Apartment is only one mile to hospital and is in walking distance to Plattsburgh State University. Perfect for Cardinal sports fans and parents as the PSUC Field house is located in the backyard. Large driveway can accommodate boats for fishing tournament guests. Unit is located upstairs with short, wide staircase. Unit is very clean and in safe neighborhood!

Guest favorite

A serene bedroom features a spacious bed with white linens and colorful accent pillows. A modern dresser with yellow accents stands nearby, accompanied by a small folding chair. Natural light enters through the window, illuminating the wide pine floor and slanted ceiling.

Apartment in Charlotte

4.94 out of 5 average rating, 280 reviews

Charlotte Private Studio Apartment with a View

Welcome to our sweet inviting studio apartment. You will enjoy the quiet rural landscape, views of the Green Mountains and Mt. Philo from your bedroom. This east facing large studio offers plenty of light and open concept living. Wide pine floors and comfortable clean surrounds make this the perfect place for two adult guests or a family with children (two adults and one or two children). All are welcome. We look forward to you being our guest.

Guest favorite

The front of the cabin is framed by lush greenery and features a welcoming red door. Around a cozy patio area, four classic Adirondack chairs are arranged, complemented by blooming flower pots offering vibrant colors.

Cabin in Keeseville

4.92 out of 5 average rating, 129 reviews

Cozy cabin w/ private lake access & hot tub

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

The cabin is nestled among tall trees, surrounded by lush greenery and landscaped gardens. Natural stone pathways and rustic wood elements define the area, leading to the structure. Vibrant plants and wildflowers add color to the scene, enhancing the serene outdoor setting.

Cabin in Schuyler Falls

4.91 out of 5 average rating, 247 reviews

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.