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

Apartment in Clintonville

4.95 out of 5 average rating, 149 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.

Oct 5 – 12

G$17,755 GYD per night

Guest favorite

Guest suite in Colchester

4.88 out of 5 average rating, 301 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 a down 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 where one can play tennis on lighted courts and swim in Lake Champlain. There is a grocery/liquor store a 5 minute walk away.n

Aug 29 – Sep 5

G$23,796 GYD per night

Guest favorite

Apartment in Hinesburg

4.96 out of 5 average rating, 399 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!”

Jan 7 – 14

G$27,950 GYD per night

Guest favorite

Home in Wilmington

4.94 out of 5 average rating, 432 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.

Mar 10 – 17

G$26,176 GYD per night

Guest favorite

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 30 – Sep 6

G$29,102 GYD per night

Guest favorite

Guesthouse in Highgate

4.97 out of 5 average rating, 533 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!

Dec 20 – 27

G$22,380 GYD per night

Guest favorite

Guest suite in Waterbury Center

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.

Apr 27 – May 4

G$11,318 GYD per night

Guest favorite

Cabin in Lyon Mountain

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

G$15,552 GYD per night

Guest favorite

Guest suite in Hinesburg

4.96 out of 5 average rating, 1117 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.

Oct 16 – 23

G$34,310 GYD per night

Guest favorite

Tiny home in Wilmington

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 11 – 18

G$29,843 GYD per night

Guest favorite

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.

May 8 – 15

G$29,035 GYD per night

Guest favorite

Cabin in Jay

4.96 out of 5 average rating, 659 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.

Feb 28 – Mar 7

G$39,456 GYD per night