Family-friendly holiday rentals in Chesterfield

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Top-rated family-friendly rentals in Chesterfield

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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, 358 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, 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 favourite
A queen-sized bed is positioned against a wooden wall with slanted ceilings. Large triangular windows provide views of the surrounding forest and mountains, allowing natural light to fill the space.
Home in Keene
4.97 out of 5 average rating, 217 reviews

Ascent House | Keene

A unique retreat meticulously crafted for resting and recharging after exploring in our beautiful Adirondack Wilderness. Flooded with natural light, every room offers calming frames of nature. Watch the sun peak through the forest and rise over the mountains through expansive windows. Ascend the levels of the house, each revealing more landscape. Experience a designer woodfired traditional Finnish sauna & totally recharge while embracing our harsh Adirondack weather. We hope you love it here.

Top Guest favourite
A cottage with a wooden exterior is nestled among greenery. A spacious deck with a railing extends from the front, featuring stairs leading down to a natural landscape. Trees surround the property, providing a sense of privacy and tranquility.
Cottage in Hinesburg
4.96 out of 5 average rating, 267 reviews

Bright new cottage in exquisite Vermont setting

Relax in "Findaway" cottage. Centrally located between Burlington and Montpelier and directly adjacent to Sleepy Hollow cross country ski and bike area, Birds of Vermont museum and the Vermont Audubon Center. Settle in and relax, hike right out the door, or sip a drink on the deck overlooking a beaver pond where you may see beaver, otters, deer, birds or even a moose! Surrounded by gardens and not far from downhill skiing and hiking options, swimming, sailing, dining and Lake Champlain.

Guest favourite
A rustic cabin features a wooden facade with a red metal roof, surrounded by colorful autumn foliage. A small porch is furnished with white chairs and a cozy couch, inviting relaxation. A rain barrel sits on the side, adding to the cabin's off-grid charm.
Cabin in Duxbury
4.9 out of 5 average rating, 272 reviews

Off Grid Vermont Cabin-Hike-Write

An off grid cabin in the hills of Vermont with a spectacular view of Camel's Hump. Not for everyone, (no running water, spotty cell service) but if you want quiet, beauty and solitude, this place is for you. A writer-hiker's dream. If it's chilly, the cabin's heated. There's also an ice pack (provided) fridge, propane stove, solar electricity for lights, composting toilet (no smell. Really), pots, cooking utensils, dishware etc We allow one dog (only ONE, please!) for a fee $25 per stay.

Top Guest favourite
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, 263 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.

Top Guest favourite
An aerial view of a charming chalet surrounded by lush greenery. A spacious wrap-around deck features outdoor seating and a red umbrella, offering a cozy area for relaxation. Sunlight filters through the trees, enhancing the natural setting.
Chalet in Jay
4.96 out of 5 average rating, 258 reviews

Adirondack Timberwolf Cabin

Cozy Mountain Chalet in Jay, NY on beautiful Glen Road. Only .7 miles to the Jay Covered Bridge, 3 miles to the Jay Mountain summit trail head, 7 miles to Whiteface Mountain, and 16 miles to Lake Placid. Keene and Keene Valley trail heads are only minutes away. The cabin has 3 acres of wooded property with a front driveway as well as a back access drivweway which is nice to walk. There is Satellite TV and wifi. There is good cell coverage. World Class Fishing, Ausable Rivers are close

Top Guest favourite
The cabin exterior is illuminated by soft lighting, highlighting the wooden structure surrounded by trees. A cozy fire pit area with red chairs, a picnic table, and an umbrella is visible, creating an inviting outdoor space for relaxation and gathering.
Cabin in Wilmington
4.99 out of 5 average rating, 329 reviews

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.

Top Guest favourite
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, 289 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.

Top Guest favourite
A lone fisherman is silhouetted in a kayak, cast against the backdrop of a vibrant sunset over the calm waters of Lake Champlain. The sky features warm hues of orange and gold, reflecting softly on the water's surface.
Guesthouse in Highgate
4.97 out of 5 average rating, 724 reviews

Beautiful lake-front cottage, Lake Champlain

Lakefront cottage located in Highgate Springs, Vermont, on the Canadian border. The 2-bedroom cottage sits adjacent to the owner-occupied main house, on a large one-acre lot, with 120 feet of Lake Champlain shoreline. Enjoy the stunning sunset views while sitting on the deck overlooking the water. Private dock included. Montreal and Burlington each 45 minutes away. Available level-2 car charger. Well-behaved pets allowed. Super-fast WIFI!

Top Guest favourite
An A-frame cabin stands under a starry night sky, with large glass doors illuminating the interior. Outdoor string lights create a warm glow along the path leading to the cabin, surrounded by trees and natural landscape.
Cabin in Jay
4.99 out of 5 average rating, 154 reviews

Aframe - Sauna, Near Lake Placid - Unique & Modern

Welcome to ADK Aframe - A luxury mid-century modern cabin! Located on a quiet road, this amazing space serves as a relaxing retreat for you to recharge after adventure filled days hiking, biking, paddling, fishing and skiing. Our pet-free home features all new furnishings and modern comforts, including a barrel sauna. The neighborhood includes private hiking/X-Country skiing trails, open space with a lake, and Ausable River access.

Top Guest favourite
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
4.93 out of 5 average rating, 148 reviews

Adirondack Cabin Retreat – Hot Tub + Lake

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.

Popular amenities for Chesterfield family-friendly rentals