
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

Metcalf Pond Camp Convenient to Smugglers Notch

Hilltop Haven

Lodge with AC & Hot Tub

Hot Tub | Bohemian Bungalow | Restaurants + Shops

Sauna, Cold Plunge, Hot Tub, Paddle Boards, Bikes

Adirondack Autumn: Unique Chalet with Hot Tub!

Woodstone Cottage an Adirondack Experience

Large Cozy Lodge Near Whiteface w/ Hottub & Sauna
Family- and pet-friendly home rentals

Aunt Shy's Hide-Away

Secluded ADK cabin | Hike @ heart of Fall Foliage

Porcupine Farm Barn

Off-Grid ADK cabin Retreat | Unplug & Reconnect

200 acre Stowe area Bunkhouse.

Adirondack Timberwolf Cabin

Large & Cozy, Scenic Walks, Private Entry, Jacuzzi

Secluded Village Gem: Cozy Studio Overlooks River!
Family-friendly home rentals with a pool

Slopeside Bolton Valley Studio

Lux Alpine Studio Ski In Ski Out. Spruce Peak 1214

Lower Yurt Stay on VT Homestead

Apartment, comfy and cozy with kitchen/gas fire

Spacious Private Apartment w/ Green Mountain Views

Bunny Hill Cabin -Pets, Shared Hot Tub & Lap Pool

Private Suite in the Green Mountains

The Whiteface Lodge Luxury Resort & Spa - Jr Suite
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Mount Pocono Holiday rentals
- The Hamptons Holiday rentals
- Quebec City Holiday rentals
- Rentals with lake access Chesterfield
- Rentals with a fireplace Chesterfield
- Rentals with a kayak Chesterfield
- Rentals with a patio Chesterfield
- Rentals with beach access Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Rentals with outdoor seating Chesterfield
- House rentals Chesterfield
- Pet-friendly rentals Chesterfield
- Waterfront rentals Chesterfield
- Rentals with a fire pit Chesterfield
- Family-friendly rentals Essex County
- Family-friendly rentals New York
- Family-friendly rentals United States
- Sugarbush Resort
- Smugglers' Notch Resort
- Spruce Peak
- Parc Safari
- Whiteface Mountain Ski Resort
- Fort Ticonderoga
- Bolton Valley Resort
- Cochran's Ski Area
- Leahy Center for Lake Champlain
- Burlington Country Club
- Ethan Allen Homestead Museum
- Country Club of Vermont
- Vermont National Country Club
- Lincoln Peak Vineyard
- Titus Mountain Family Ski Center
- North Branch Vineyards
- Shelburne Vineyard
- Autumn Mountain Winery
- Snow Farm Vineyard & Winery
- Boyden Valley Winery & Spirits