
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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesterfield family-friendly rentals
Family-friendly home rentals with a hot tub

Camp Serenity

Honeymoon Cabin with Jacuzzi Tub

Charming getaway tucked away in the Green Mtns

3 BDR Mtn Home near wedding barns, Smuggs/Stowe

Hilltop Haven

White Spruce Cottage ~ Wilmington/Whiteface Mtn NY

The Brookside @ Wilmington, NY

Breathtaking View, Hot Tub, Sauna, Pets Ok!
Family- and pet-friendly home rentals

Schroon River Cabin

Tiny House at Camp Comyns

Running Brook

Birchwood Lodge - Our Home in the Woods

Bell Meadow Cottage

Hancock hideaway

Rockhaven - Kibbe point cottage

Organic Farm Hideaway Home and Pond
Family-friendly home rentals with a pool

Green Mountain Getaway

Swiss Condo #2 - Water Access

Ski In/Ski Out with upgrades!

Epic Views of the Green Mountains

Minutes from Main St STR-200402

TWO BEDROOM RENOVATED MOUNTAIN VIEW CONDO

Cozy two-bedroom cabin near Smugglers Notch

Apartment, comfy and cozy with kitchen/gas fire
Destinations to explore
- Montreal Holiday rentals
- Hudson Valley Holiday rentals
- Boston Holiday rentals
- Québec City Holiday rentals
- The Hamptons Holiday rentals
- Long Island Holiday rentals
- Plainview Holiday rentals
- Pocono Mountains Holiday rentals
- East River Holiday rentals
- New York Holiday rentals
- Greater Toronto Area Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Rentals with lake access Chesterfield
- Pet-friendly rentals Chesterfield
- House rentals Chesterfield
- Rentals with a fireplace Chesterfield
- Rentals with a kayak Chesterfield
- Rentals with a firepit Chesterfield
- Rentals with outdoor seating Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Family-friendly rentals Chesterfield
- Rentals with a patio Chesterfield
- Waterfront rentals Chesterfield
- Rentals with beach access Chesterfield
- Family-friendly rentals Essex County
- Family-friendly rentals New York
- Family-friendly rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
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- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
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- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Sugarbush Resort
- Smugglers' Notch Resort
- Parc Safari
- Spruce Peak
- Bolton Valley Resort
- Fort Ticonderoga
- Cochran's Ski Area
- Whiteface Mountain Ski Resort
- Country Club of Vermont
- Vermont National Country Club
- Ethan Allen Homestead Museum
- Leahy Center for Lake Champlain
- Cozy Cottages & Otter Valley Winery
- Lincoln Peak Vineyard
- Burlington Country Club
- Autumn Mountain Winery