
Family-friendly vacation rentals in Sheffield
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Sheffield
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 Sheffield family-friendly rentals
Family-friendly home rentals with a hot tub

Artist Cottage

40-Foot Container Cabin in the Catskills

Boutique TINY home+private hot tub-walk to Main St

Unwind in the country, stargaze in hot tub

Tiny house on the Esopus creek

Jaw dropping mountain & lake views

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

The Red Cabin-Secluded Getaway with backyard Brook
Family- and pet-friendly home rentals

3-bedroom Berkshire bungalow on 2.5 peaceful acres

Eco Cottage in the Woods

1930's Cottage charm cozy air cond. near hiking

Pine Plains Cottage

Cosy Catskill Casita in the Middle of Village

Harmony Valley Home, bright & inviting studio

Sweet Victorian in Housatonic

Cabin Nestled in the Litchfield Hills
Family-friendly home rentals with a pool

Sweet Farm Stay

Country Getaway Tiny House in woods w/Pool/Sauna

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

The Copake Cabin - A rustic-modern retreat.

Sackett & Van Dam Guest House @ Little 9 Farm 1706

Modern Upstate Cabin, near Rhinebeck NY

Charming Lakefront Cabin with Hot Tub

Le Soleil Suite - Fire pit, Views 10 Min To Hudson
Quick stats about vacation rentals that are family-friendly in Sheffield
Total rentals
70 properties
Nightly prices starting at
R2,427 ZAR before taxes and fees
Total number of reviews
2.9K reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Wifi availability
70 properties include access to wifi
Destinations to explore
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- Rentals with a fire pit Sheffield
- Pet-friendly rentals Sheffield
- House rentals Sheffield
- Rentals with a washer and dryer Sheffield
- Rentals with a patio Sheffield
- Rentals with a fireplace Sheffield
- Rentals with outdoor seating Sheffield
- Family-friendly rentals Berkshire County
- Family-friendly rentals Massachusetts
- Family-friendly rentals United States
- Hunter Mountain
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Thunder Ridge Ski Area
- TPC River Highlands
- Bash Bish Falls State Park
- Zoom Flume
- Kent Falls State Park
- Walkway Over the Hudson State Historic Park
- Catamount Mountain Ski Resort
- Bushnell Park
- Mount Greylock Ski Club
- Norman Rockwell Museum
- Windham Mountain
- Wintonbury Hills Golf Course
- Taconic State Park
- Dinosaur State Park
- Mount Sugarloaf State Reservation
- Opus 40
- Mount Southington Ski Area
- Mohawk Mountain Ski Area
- Mount Tom State Reservation
- Hartford Golf Club