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.

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Guest favorite

Home in Willsboro

4.96 out of 5 average rating, 104 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!

Guest favorite

A charming cottage features a combination of stone and log exterior, framed by vibrant trees in autumn colors. A green pitched roof complements the rustic design. The front yard is adorned with a variety of plants and seating arrangements, creating a serene environment.

Castle in Schuyler Falls

4.92 out of 5 average rating, 363 reviews

Woodstone Cottage an Adirondack Experience

Woodstone Cottage is a cozy stone and log building, located between lake champlain and whiteface moutian, sitting on a 109 acres sided by Salmon River, with gorgeous hiking trails. If you're looking to enjoy a warm outdoor jacuzzi, warm sauna bath or a relaxing night with fire on a clear sky, look no further. It is a haven for a romantic getaway, a skiing experience, or a relaxing family time in the nature. If this isn't available, check my other similar property Adirondack House Experience.

Superhost

A raised ranch home is depicted, featuring a light-colored exterior with a red front door. Windows are framed symmetrically on either side, and a small gravel path leads to the entrance. The front yard is landscaped with greenery and flowers, providing a welcoming appearance.

Guest suite in Colchester

4.87 out of 5 average rating, 370 reviews

Malletts Bay Flat

Newly remodeled with a separate entrance to first level of a raised ranch home. Private bathroom, queen sized bed and sitting area. There are down pillows and comforter on the bed. Eating area with table and chairs, microwave and fridge. Heated by a gas stove. We are a 10 minute drive to Burlington and a 10 minute walk to Bayside Beach and Park with lighted tennis courts and beach. There is a grocery/liquor store a 5 minute walk away. No pets allowed due to severe allergies in family member.

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, 166 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.

Top guest favorite

An open interior perspective of a yurt reveals a cozy seating area with plush pillows and a patterned blanket. Above, a skylight allows natural light to illuminate the space. A staircase leads to a lofted area, while a dining set is positioned in the background.

Yurt in New Haven

4.92 out of 5 average rating, 286 reviews

Song Bird Sangha Yurt

Songbird Sangha was thoughtfully created to provide a peaceful retreat from the world. It is nestled into a beautiful forest with privacy in mind. You will fall in love with the sky dome over your queen sized bed for the most comfortable star gazing ever! Your stay would not be complete without a complimentary campfire & marshmallow and if you would like more magic sign up for our Airbnb Experience The Healing Nature of Horses, a life enhancing encounter . Certified Wildlife Habitat.

Guest favorite

The kitchen area features wooden cabinetry, equipped with a gas stove, microwave, and refrigerator. A double sink is positioned beside a dish rack. Light enters through a window draped with sheer curtains, complementing the granite countertops and tiled backsplash.

Apartment in Old North End

4.88 out of 5 average rating, 453 reviews

Quiet and Cosy homestead. Your own private place.

This place is close to city center, nightlife, public transport, the airport, UVM Medical Center, along with multiple colleges (UVM and Champlain College to name a few), very family-friendly place. You’ll love this place because of its coziness, location and accessibility, people and the views. This place is great for couples, solo adventurers, business travelers, and families (with kids). Location is everything and this place has it all, it's your Home Away From Home.

Top guest favorite

A sprawling meadow extends towards distant mountains, with a varied landscape marked by trees and fields. The sky is partially covered with clouds, offering a serene view of the natural surroundings and hints of autumn colors in the foliage.

Home in Wilmington

4.95 out of 5 average rating, 492 reviews

THE VIEW! THE VIEW! THE VIEW!

A 1900 farmhouse that has been in the family for generations. Recently renovated to accommodate up to 5 guests, it is clean with simple furnishings and a SPECTACULAR VIEW! Located RIGHT ON NYS RTE 86 (close to the road) with easy access to nearby attractions. The house is split in 2 and is designed for 2 families. I rent out "The View" using airbnb exclusively. My wife and I reside in the back portion of the house with a separate entrance and separate parking.

Guest favorite

A cozy sitting area features a couch and an armchair, complemented by decorative cushions. Wall art is displayed above a television, and a kitchenette is visible in the background. Warm lighting enhances the inviting atmosphere in this thoughtfully arranged space.

Guest suite in Waterbury Center

4.93 out of 5 average rating, 454 reviews

Waterbury Center Guest Bedroom - 244 Howard

The guestroom room is very cozy with radiant heat in the floor during the winter. The separate entrance is off a covered porch. The porch has chairs and a table and is very pleasant in the warmer months The little kitchen alcove is convenient for coffee or tea or a light meal. We live in a historic building and our neighborhood is located very close to Rte 100. Waterbury village and Stowe as well as skiing, hiking and biking are all nearby.

Guest favorite

The cabin exterior features a brown wood paneling with a white door and a window on each side. A small deck is present, offering two chairs and a table adorned with a basket of flowers, surrounded by greenery.

Cabin in Lyon Mountain

4.89 out of 5 average rating, 232 reviews

Adirondack Wilderness Cabin

Adirondack cabin located in a gated small RV Park. Beautiful lake views from the RV Park and amazing night time skies. Close to hiking trails and boating opportunities. Located in Lyon Mountain, NY. Four miles to Chazy Lake Beach or to the Chateaugay Lake Boat Launch. Hike the beautiful Lyon Mountain to the fire tower. Hike is 7.1 miles. One hour to Lake Placid and Montreal.

Top guest favorite

The retreat is a rustic two-story building made of wood, surrounded by lush greenery. A gravel path leads to a fire pit area with four Adirondack chairs arranged on a grassy lawn, offering a peaceful outdoor space for relaxation.

Home in Ellenburg Center

4.96 out of 5 average rating, 122 reviews

Adirondack Panther Mountain Retreat

Adirondack Great Camp–inspired retreat tucked in a peaceful country setting near two mountain lakes. It offers rustic charm, is immersed in nature, and has easy access to Burlington, Montreal, Lake Placid & Plattsburgh. Perfect for hiking, cycling, or unplugging in nature. Ideal for couples, solo adventurers & business travelers seeking quiet, comfort, and scenic beauty.

Top guest favorite

A rustic barn features a combination of wood siding and a dark metal roof, set against a clear blue sky. The structure includes multiple windows and a peaked section at the top. A porch with chairs is visible in the foreground, surrounded by well-maintained grass.

Guest suite in Hinesburg

4.97 out of 5 average rating, 1,273 reviews

Boston Magazine Pick! Barn Loft

*** Chosen by Boston Magazine as one of five New England barns to rent! *** Our beautiful barn loft in Hinesburg is close to Burlington, the Green Mountains and Lake Champlain. It features a new kitchen, cathedral ceilings, plenty of natural light, rustic charm and lovely views. The space has its own entrance and is completely separate and private from the main house.

Top guest favorite

The exterior of a cozy A-frame cabin is presented, featuring multi-colored siding and a prominent central entrance. Wooden steps lead to the door, flanked by flower boxes. Surrounded by a grassy area and trees, the setting offers a natural, serene environment.

Cabin in Jay

4.96 out of 5 average rating, 737 reviews

Adirondack Mountainside A-Frame

A cozy pet friendly A-frame nestled in the Jay Range with view of Whiteface Mountain. The home features a living room, fireplace, loft bedroom and fully equipped kitchen. With endless activities to choose from, we are located just 10 minutes from Whiteface Mountain and 20 minutes from Lake Placid.