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

Macintosh Hill Farm

Charming getaway tucked away in the Green Mtns

Hilltop Haven

Killington area home - 4-seasons & hot tub

Breathtaking View, Hot Tub, Sauna, Pets Ok!

Woodstone Cottage an Adirondack Experience

#7 - Hemlock Hideaway Cabin

The Barn at Fielder Farm
Family- and pet-friendly home rentals

Schroon River Cabin

Hideaway Cabin by the Stream on 27 Acres

Moon Valley Country Retreat no clean fee pets yes

Mid century modern gem with views of Sugarbush

The McKinley House

Wilmington Range Log Cabin on the AuSable River

The Guest House at Sky Hollow

Historic Icehouse in 980 Acres Private Wilderness
Family-friendly home rentals with a pool

Chilson Brook Alpacas

Cozy, spacious, 3 bedrooms, 4 beds, swimming pool.

Relax in Recreation Paradise!

Luxury Alpine Studio. Ski In Ski Out. Spruce Peak

Lower Yurt Stay on VT Homestead

Gorgeous panoramic views - 4 miles to the mountain

EPIC Stowe Getaway - Great For Families & Friends

Cute Cottage - Poolside - Minutes To Activities
Quick stats about vacation rentals that are family-friendly in Middlebury
Total rentals
40 properties
Nightly prices starting at
R1,596 ZAR before taxes and fees
Total number of reviews
2.2K reviews
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Destinations to explore
- 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
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- 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
- Okemo Mountain Resort
- Smugglers' Notch Resort
- Gore Mountain
- Spruce Peak
- Fort Ticonderoga
- Bolton Valley Resort
- Pico Mountain Ski Resort
- Cochran's Ski Area
- Whiteface Mountain Ski Resort
- Autumn Mountain Winery
- Country Club of Vermont
- Fox Run Golf Club
- Northeast Slopes Ski Tow
- Cozy Cottages & Otter Valley Winery
- Vermont National Country Club
- Leahy Center for Lake Champlain
- Ethan Allen Homestead Museum
- Lucky Bugger Vineyard & Winery
- Lincoln Peak Vineyard
- Adirondack Extreme Adventure Course
- Killington Adventure Center
- Burlington Country Club
- Montshire Museum of Science