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 favourite

Cottage in Lincoln

4.87 out of 5 average rating, 857 reviews

The Barn at North Orchard, Near Middlebury

Our barn sits on an 80 acre estate with fab views of the Green Mts. near Middlebury/Burlington. Perfect for 2 adults and a child or grandparents/ 2 friendly couples. Close to skiing, hiking, lake & river swimming, great restaurants... local beer, wine, cheese!. Want yoga, pasta class, or massage? We will gladly hook you up. Or, you could stay in to read, work, and enjoy the serenity of the mountains. A very private garden patio for morning coffee/ afternoon beer or wine or awaits you.

Feb. 5 – 12

$188 CAD per night

Guest favourite

Yurt in New Haven, Vermont, US

4.91 out of 5 average rating, 254 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.

Aug. 29 – Sep. 5

$201 CAD per night

Guest favourite

Apartment in Clintonville, New York, US

4.95 out of 5 average rating, 148 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 Cham, 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 family time. The apartment had a unique style of it's own that will provide you a comfortable and reasonable price place to stay.

Mar. 20 – 27

$136 CAD per night

Guest favourite

Home in Wilmington, New York, US

4.94 out of 5 average rating, 430 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.

Nov. 26 – Dec. 3

$181 CAD per night

Guest favourite

Guesthouse in Plattsburgh

4.95 out of 5 average rating, 229 reviews

Studio Cottage/Lake Champlain

This is a stand alone studio cottage with a lovely screened porch. Our cottage is located on our 7 acre residential lot. This is not a rural property. We work hard on all our gardens, with a lovely pond . Perfect spot to enjoy the Autumn foliage as well to go off leaf peeping in the Adirondacks. You can take advantage of the Plattsburgh City Beach and two Local State park beaches within a few minutes drive, all beaches offer a sandy beach, and swimming.

Aug. 26 – Sep. 2

$207 CAD per night

Guest favourite

Guesthouse in Highgate

4.98 out of 5 average rating, 529 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!

Mar. 6 – 13

$161 CAD per night

Guest favourite

Guest suite in Waterbury Center, Vermont, US

4.94 out of 5 average rating, 415 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.

Dec. 4 – 11

$82 CAD per night

Guest favourite

Cabin in Lyon Mountain, New York, US

4.9 out of 5 average rating, 193 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.

Sep. 15 – 22

$110 CAD per night

Guest favourite

Guest suite in Hinesburg, Vermont, US

4.96 out of 5 average rating, 1112 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.

Sep. 24 – Oct. 1

$254 CAD per night

Guest favourite

Tiny homes in Wilmington, New York, US

4.96 out of 5 average rating, 545 reviews

Adirondack Cordwood Cabin Whiteface 2 miles

Handcrafted 22’ octagonal cordwood cabin with eco-friendly design, 8’ x 8’ bathroom, living roof, and colorful bottle logs. Features full kitchen, grill, fire pit, and linens. Sleeps two with a queen bed and futon. Storage shed included. Near skiing, fishing, hiking, and biking. Flexible stay length and complimentary cleaning service.

Jun. 8 – 15

$209 CAD per night

Guest favourite

Cabin in Vermontville

4.99 out of 5 average rating, 229 reviews

The East Lake Cabin at Camp Arden

Enjoy the weather on the large screened-in porch. This English, Adirondack style cabin is perfectly positioned to take advantage of all the Adirondacks' has to offer. Take a paddle on Carpenter Pond with a provided canoe, or snuggle by the fire outside. No matter what you do, Camp Arden is waiting to help you enjoy the Adirondacks.

Oct. 14 – 21

$200 CAD per night

Guest favourite

Cabin in Jay, New York, US

4.96 out of 5 average rating, 657 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.

Apr. 13 – 20

$288 CAD per night