
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.
Vacation 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

Backyard Bunker Retreat

Charming Private Apt in South End w/ Hot Tub

Cozy Cabin -Top of Hill with Views

Adirondack Autumn: Unique Chalet with Hot Tub!

Lewis Brook Lodge

Woodstone Cottage an Adirondack Experience

Guest Suite w/hot tub & fireplace

Fox Den Tiny House w/hot tub 1min to Smuggs
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

VT Hideaway studio: breweries,hiking, dogs welcome

Downtown Charm:A Unique Airbnb Experience Historic

Edin's Chalet Adirondacks-Whiteface 4 Beds-2 Baths

Adirondack Cozy Log Cabin
Family-friendly home rentals with a pool

Lux Alpine Studio Ski In Ski Out. Spruce Peak 1214

Epic Views of the Green Mountains

Lower Yurt Stay on VT Homestead

Apartment, comfy and cozy with kitchen/gas fire

Spacious Private Apartment w/ Green Mountain Views

Private Suite in the Green Mountains

Large Cozy Lodge Near Whiteface w/ Hottub & Sauna

Ski in/out Condo @ The Lodge at Spruce Peak
Quick stats about vacation rentals that are family-friendly in Chesterfield
Total rentals
60 properties
Nightly prices starting at
$112 CAD before taxes and fees
Total number of reviews
2.9K reviews
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
60 properties include access to wifi
Destinations to explore
- Plainview Vacation rentals
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- Waterfront rentals Chesterfield
- Rentals with a fireplace Chesterfield
- Rentals with a kayak Chesterfield
- Pet-friendly rentals Chesterfield
- Rentals with a washer and dryer Chesterfield
- House rentals Chesterfield
- Rentals with lake access Chesterfield
- Rentals with beach access Chesterfield
- Rentals with a patio Chesterfield
- Rentals with a firepit Chesterfield
- Rentals with outdoor seating 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
- Bolton Valley Resort
- Whiteface Mountain Ski Resort
- Fort Ticonderoga
- Cochran's Ski Area
- Autumn Mountain Winery
- Country Club of Vermont
- Burlington Country Club
- Leahy Center for Lake Champlain
- Ethan Allen Homestead Museum
- Vermont National Country Club
- Lincoln Peak Vineyard
- Titus Mountain Family Ski Center
- Boyden Valley Winery & Spirits
- Snow Farm Vineyard & Winery
- Shelburne Vineyard
- North Branch Vineyards