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

Home in Willsboro

4.96 out of 5 average rating, 102 reviews

"Beau Overlook Cottage" your room with a view!

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 fresh water tumbling over river rocks just below. This home is situated 2 miles south of the Lake Champlain ~ Boquet River Delta. The scene at the sand bar of the delta is just as beautiful as it sounds. This relaxing sanctuary will provide an upscale and sophisticated home, whose logistics can't be beat!

Guest favorite

Home in Malletts Bay

4.91 out of 5 average rating, 132 reviews

Private lakefront oasis

Our year round, pet friendly cottage is " the perfect place for quality family time and peaceful reflection". QB in open upstairs loft. The open floor plan includes a FB in the newly renovated downstairs bedroom, an office, and a sofa bed in the living area. Bathroom is small, but fully functional. Fully equipped kitchen, wifi and cable. Private patio with cabana bar, world-class Causeway bike path and excellent fishing, all located 10- miles from downtown Burlington and colleges. 1-dog only.

Guest favorite

Rental unit in Clintonville

4.96 out of 5 average rating, 162 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.

Superhost

Yurt in Jay

4.91 out of 5 average rating, 452 reviews

Adirondack Mountain Yurt at Blue Pepper Farm

Escape to our 30’ yurt atop a 25-acre pasture with breathtaking views of Whiteface mountain. Accommodating 2 to 6 guests, it’s perfect for family outings or adventures with friends. A winter camping experience: the yurt features basic insulation and is heated by a wood stove, with firewood for purchase on-site. Bring sleeping bags and slippers for warmth in colder temps. Embrace nature’s beauty—plan accordingly, read our reviews, and feel free to ask any questions. Your adventure awaits!

Guest favorite

Cabin in Jay

4.96 out of 5 average rating, 113 reviews

Cozy Cabin in the Adirondacks

We welcome you to our Cozy Cabin in the Adirondacks, located in Jay, New York, in the heart of the High Peaks. You will be 11 miles from Whiteface Mtn, and close to Lake Placid, AuSable Chasm, fishing on the Ausable River, Lake Champlain and only 90 miles from Montreal. The Cabin has been recently totally remodeled, and we think you will enjoy the newly tiled bathrooms, renovated kitchen, and cozy living room area with highspeed Wifi, cable tv, and even a computer station with a printer.

Guest favorite

Rental unit in Hinesburg

4.97 out of 5 average rating, 433 reviews

The Perfect Cozy Weekend Escape

From our reviews: "We were amazed with this place - could not have asked for a more perfect place to stay - immaculate - super comfortable bed! - wonderfully inviting - the photos do not do it justice at all - A picturesque Vermont country setting - The perfect retreat to get away from it all! - impeccably clean - simply fantastic - total privacy & idyllic setting - far exceeded our expectations! - perfect for a weekend escape - a space to feed your soul - absolutely amazing!”

Guest favorite

Home in Wilmington

4.94 out of 5 average rating, 467 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

Guesthouse in Highgate

4.97 out of 5 average rating, 606 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!

Guest favorite

Guest suite in Waterbury Center

4.94 out of 5 average rating, 444 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

Guest suite in Hinesburg

4.96 out of 5 average rating, 1,208 reviews

Boston Magazine Pick! Barn Loft

*** Chosen by Boston Magazine as one of five New England barns to rent! *** Beautiful barn loft close to Burlington, the Green Mountains and Lake Champlain. Air conditioning, 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.

Guest favorite

Cabin in Jay

4.96 out of 5 average rating, 703 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.