Family-friendly holiday rentals in Chesterfield

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Top-rated family-friendly rentals in Chesterfield

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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, 360 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.

Guest favourite
A cottage is seen perched on a grassy bank, overlooking a river. Tall trees frame the scene, providing a natural backdrop. The water's surface reflects the surroundings, while a hint of light is visible from the cottage window, suggesting warmth inside.
Home in Willsboro
4.97 out of 5 average rating, 116 reviews

"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!

Top guest favourite
A cozy living space features two striped armchairs and a woven coffee table adorned with a vase of sunflowers. A well-equipped kitchen, visible in the background, includes wood cabinetry and modern appliances. Natural light fills the room, enhancing the inviting atmosphere.
Cottage in Panton
4.97 out of 5 average rating, 259 reviews

Panton / Near Vergennes , Middlebury Private Home

Begin your Vermont experience at our serenely secluded, wooded hide–a-way. This inviting private home features all the best amenities including luxury linens, fully equipped kitchen, bath with custom over sized shower, a beautiful deck with gas grill, teak and glass dining table, and lounge seating for 4. It is the perfect space for 2 adults and children, or up to 4 adults, providing easy access to the best Vermont has to offer from Lake Champlain, Vergennes, Middlebury, and all points beyond.

Top guest favourite
A modern living room showcases a gray sectional sofa adorned with colorful pillows, accompanied by a cozy armchair. A glass coffee table is centered on a plush area rug, with a decorative mirror and plants enhancing the space. Natural light filters through white curtains.
Flat in Colchester
5 out of 5 average rating, 139 reviews

Boho Getaway near Burlington, Beach, & Bike Path!

Welcome to our Airbnb! Mid-century modern design with boho vibes! Less than 15 min drive to downtown Burlington - easy access to the shops & restaurants on Church Street! ~12 min walk to sandy Thayer Beach! Bike to the Causeway or along the lake into Burlington! Store your bikes in the convenient bike shed. Inside...enjoy the 55" TV, FAST WiFi, comfy beds, air conditioners, washer & dryer, and a kitchen stocked with all the essentials - including a Keurig machine & K-Cups. Off-street parking.

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
4.98 out of 5 average rating, 222 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 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
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.
Flat in Clintonville
4.88 out of 5 average rating, 264 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 captures the cozy chalet nestled among lush green trees, with distant mountain peaks visible in the background. The cabin is surrounded by a spacious outdoor area, showcasing a wrap-around deck that invites relaxation.
Cabin in Jay
4.96 out of 5 average rating, 259 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

Guest favourite
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 favourite
The living room features a cozy seating area, including a light gray sofa and a recliner. Large windows with sheer curtains allow natural light to fill the space, while wooden accents, including a unique table, add character to the setting.
Flat in Jay
4.94 out of 5 average rating, 135 reviews

"Gateway To The Adirondacks" on Main Street

Situated in the heart of the village on Main Street in Au Sable Forks, the "Gateway to the Adirondacks", you'll find this newly renovated second floor apartment. This spacious unit offers a fully equipped kitchen, two bedrooms, full bath and comfortably furnished living room with Smart TV and WiFi. Conveniently located within walking distance to grocery stores, pub, eateries, and entertainment. Enjoy fishing, biking, hiking, Whiteface Mountain and Lake Placid.

Top guest favourite
The exterior of the guesthouse is shown, featuring a white wooden facade with multiple windows. A prominent cupola tops the structure, reflecting sunlight under a clear blue sky. Lush green trees and shrubs surround the building, enhancing the serene ambiance of the area.
Guest house in Vergennes
4.98 out of 5 average rating, 132 reviews

Private Guesthouse in the heart of Vergennes

Completed in 2013, the Guesthouse perfectly complements the 1871 Victorian home to which it is attached. Located on Main Street in historic Vergennes, Vermont, our home is one of several fine examples of the architecture of the 19th Century that grace our City. Our thriving downtown is a short walk away, boasting exceptional dining and shopping opportunities. Vergennes is a 20-minute drive away from Middlebury College, and 45 minutes from Burlington.

Popular amenities for Chesterfield family-friendly rentals