
Family-friendly holiday 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.

Chalet Sonsie: A Sweetwater Stay
Chalet Sonsie is a freshly-renovated waterfront getaway, where you can enjoy breathtaking views of Forest Lake year-round, from every room and all 3 levels of decks! Whether you're traveling with the kids, friends, or just looking for a quiet fishing retreat, there's something here for everyone. This cozy 2-bedroom home features 2 full kitchens, 1.5 baths, expansive fireplace and TV, plus a game room complete with foosball and mini-arcade! Book today, or check out other Sweetwater Stays! -Patti

Governer's Brook Camp - 2 Bedroom
Renovated camp, 800 sq ft, near Brattleboro VT & Lake Spofford NH. Hiking trails start at the backyard. I15 minutes to Brattleboro, 5 minutes to the boat ramp on Connecticut River, 15 minutes to Lake Spofford, and 50 minutes to Mt. Snow. Across the road is a (seasonal) tumbling waterfall and gorge called “the Devils Den”. The backyard leads to woodlands with miles of trails. Enjoy a relaxing evening by the firepit overlooking the brook. Or outdoor cooking on a propane grill. ...2 Kayaks.

Monadnock Sunrise Forest Hideaway
Enjoy a converted camper as your private getaway in Southern VT. Less than 10 min to downtown Brattleboro, yet nestled in the woods for a quiet retreat. Full galley kitchen and living/lounge area. Wood stove for primary heating (electric backup for not so cold days). Outdoor spaces include a fire pit, deck, pool table, hot outdoor shower, outhouse (composting toilet), and forest for galavanting. The place is a perfect fit for two adults (queen bed) and one kid (63" long fold down couch).

Sweet Vermont Tiny Home Get Away
Your unique Vermont retreat is just a click away! Come stay in this custom built tiny house in southern Vermont. We are an easy walk to the train station, art museum, restaurants, shops, and many beautiful nature spots in and around Brattleboro VT, plus a 40 minute drive to the Mount Snow ski area, and local hiking, swimming, boating, skiing, and skating opportunities. A nature lover's paradise! Enjoy the great outdoors and small town living, or cozy up in the tiny house and just relax.

River View apartment
Beautiful completely furnished 1 bedroom apartment with a private driveway and deck. Less than a half hour from skiing and 5 min away from snowmobile trails. It is located along the west river where every summer you can go tubing, swimming, or kayaking. Across the river is a bike/walking path that leads right to the Marina restaurant on Putney Rd in Brattleboro. Bakery/café, Art Gallery and Retreat Farm all close by A gorgeous view of the river and mountain across the street .

Apple Blossom Cottage: A Tiny House
The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

Bright and Modern Chestnut Street Apartment
Enjoy a unique stay at this central, beautifully-remodeled apartment in quaint Brattleboro, Vermont. The apartment is attached to the back of the charming 1914 home where I live, and has a private, separate entrance so guests can come or go as they please. This carefully-curated apartment includes tasteful decor, a well-appointed kitchenette, organic cotton sheets, and natural bath products. Just off Hwy 91, the apartment is located in the quiet, historic neighborhood of Esteyville.

Inviting studio apartment above barn in Vermont
This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. I am as close or as far away as you would like me to be with my house right next door.

Contemporary forest eco-retreat, mountain views
This is an open, light-filled one-Bdm apartment on the lower level of our hillside home, surrounded by forests, with stunning views. Your space is 719 sf + access to laundry. We are fully vaccinated, and ask the same of guests. If you think you may have Covid please tell us. We welcome all kinds of people, regardless of race, ethnicity, gender, etc. We may ask questions before accepting people who don’t have many prior reviews. We don't take pets, sorry.

Spacious Brattleboro home on river, walk to town
Spacious 3,000 sq. ft. home with 4 bedrooms (3 queens, 2 twins) and 4 bathrooms, 3 en-suite. Enjoy a formal living room with grand and upright pianos, a cozy TV room, and a fully equipped kitchen with eat-in area leading to a deck with stunning river and mountain views. Formal dining seats 12. Expansive grounds are perfect for relaxing or hosting special events. Just a 10-min walk to Brattleboro’s Main Street shops, cafes, and culture.

Cute, Quiet, Art-Filled Apt.
This above-garage apartment is cozy and comfortable. Perfect getaway! Just 1.5 miles from Peterborough in the beautiful Monadnock region this gem has easy access to trails (backyard) and lakes. Quality linens, tasteful decor, great coffee and a spot to stash all your gear in the breezeway. Guests share main entrance with owners (but separate dwelling) who respect your privacy. Apartment access thru narrow stairs off breezeway.

Romantic Vermont Cabin|Lovely Drive to Ski Resorts
A romantic and private getaway on a peaceful six-acre farm with views of fields and forest. ☽ Featured in STAY; Gorgeous Cabins of the East Coast ☽ Elevated design; thoughtful lighting; deeply romantic ☽ Quiet & private; star-studded skies ☽ Woodstove, deck, reading nook, firepit ☽ Local's Area Guide with our favorite spots ☽ Strong wifi, no TV ☽ Scrupulously clean using unscented products
Popular amenities for Chesterfield family-friendly rentals
Family-friendly home rentals with a hot tub

Mountain View 4x4 Rustic Cabin Retreat w/Fireplace

Private Apt. on Farm, Hot Tub with views!

Secluded Farmhouse Retreat - stunning views

Vermont Farm Schoolhouse w/ Hot Tub, Sauna & Views

Boulder House - Extraordinary Luxury in the Woods!

Summit View Ski and Golf Retreat w/hot tub & Sauna

Modern Downtown 12ppl Hot Tub Fire Pit Games

Mountain side acres
Family- and pet-friendly home rentals

#32 Top Floor-Newly Renovated! Room 32-Horizon Inn

Peaceful Cabin in the Woods

Triggers Cabin

The Brick House on Washington Street

Private Cabin/PetsOK/Minutes to Okemo/Fast Wifi

Log Cabin, King Beds & 7 Min from Stratton Mtn

Peaceful Beautiful Mountain Home Spectacular Views

Modern Spacious Home with Mountain Views
Family-friendly home rentals with a pool

Bear's Den - Mt Snow Townhome w/ Ski Home Trail!

One Bedroom Suite Near Okemo

Beautiful rustic woods and fields retreat.

Cozy Vermont Antique Sugar House with Fireplace

Silver Brook Cabin

In-law Apartment, Full Kitchen, Near Mt Wachusetts

Hollywood Bungalow in the Berkshires #C0191633410

Sunlit Cozy Log Cabin 8 Private Acres By Colleges
Quick stats about holiday rentals that are family-friendly in Chesterfield

Total holiday rentals
Explore 10 holiday rentals in Chesterfield

Nightly prices starting at
Chesterfield holiday rentals start at £75 per night before taxes and fees

Verified guest reviews
Over 670 verified reviews to help you choose

Wifi availability
10 of Chesterfield holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chesterfield rentals

4.9 Average rating
Chesterfield stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
- Plainview Holiday rentals
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- Rentals with a patio Chesterfield
- Rentals with lake access Chesterfield
- Pet-friendly rentals Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Rentals with outdoor seating Chesterfield
- Waterfront rentals Chesterfield
- Rentals with a firepit Chesterfield
- Family-friendly rentals Cheshire County
- Family-friendly rentals New Hampshire
- Family-friendly rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Pats Peak Ski Area
- Jiminy Peak Mountain Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- Stratton Mountain Resort
- Mount Snow Ski Resort
- Fox Run Golf Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Crotched Mountain Ski and Ride
- Mount Sunapee Resort
- Emerald Lake State Park
- Mount Greylock
- Mount Holyoke College
- Smith College
- University of Massachusetts Amherst
- Southern Vermont Arts Center
- Massachusetts Museum of Contemporary Art
- Mount Monadnock
- Look Memorial Park
- Magic Wings Butterfly Conservatory and Gardens
- Camp Plymouth State Park




