
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

Lower Yurt Stay on VT Homestead

River Road Log Lodge overlooking Whiteface Mt

TheADKChalet w/ Hot Tub (Adirondacks)

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

Adirondack Summer: Unique Chalet with Hot Tub!

Woodstone Cottage an Adirondack Experience

Summer Fun Mins White Face-Hot Tub-Dogs Wlcm

Luxury Glass Tiny House - Mountain View + Hot Tub
Family- and pet-friendly home rentals

Secluded ADK cabin | Hike @ heart of Fall Foliage

Off-Grid ADK cabin Retreat | Unplug & Reconnect

Downtown Burlington, Renovated, 1 bedroom+

200 acre Stowe area Bunkhouse.

Warner's Camp River House, Sauna & Swimming Hole

The Trailhead

Downtown Charm:A Unique Airbnb Experience Historic

Large & Cozy, Scenic Walks, Private Entry, Jacuzzi
Family-friendly home rentals with a pool

Chilson Brook Alpacas

Epic Views of the Green Mountains

Stowe, Newly Renovated Topnotch Resort Townhouse

Apartment, comfy and cozy with kitchen/gas fire

Spacious Private Apartment w/ Green Mountain Views

Gorgeous panoramic views - 4 miles to the mountain

Amazing location, views, shared hot tub in Stowe!

Large Cozy Lodge Near Whiteface w/ Hottub & Sauna
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
- Waterfront rentals Chesterfield
- Rentals with a fire pit Chesterfield
- Rentals with a patio Chesterfield
- Rentals with lake access Chesterfield
- Rentals with a fireplace Chesterfield
- Rentals with a kayak Chesterfield
- Rentals with outdoor seating Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Rentals with beach access Chesterfield
- House rentals Chesterfield
- Pet-friendly rentals Chesterfield
- Family-friendly rentals Essex County
- Family-friendly rentals New York
- Family-friendly rentals United States
- Sugarbush Resort
- Smugglers' Notch Resort
- Parc Safari
- Spruce Peak
- Whiteface Mountain Ski Resort
- Fort Ticonderoga
- Bolton Valley Resort
- Cochran's Ski Area
- Cozy Cottages & Otter Valley Winery
- Ethan Allen Homestead Museum
- Burlington Country Club
- Leahy Center for Lake Champlain
- Vermont National Country Club
- Country Club of Vermont
- Lincoln Peak Vineyard
- Titus Mountain Family Ski Center
- North Branch Vineyards
- Shelburne Vineyard
- Boyden Valley Winery & Spirits
- Snow Farm Vineyard & Winery