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

The Rabbit Hole - Luxury Cabin in heart of Stowe

Top of the World! Jacuzzi! Private Hiking Trails!

Killington Chalet - Hot Tub, Sauna, Boot Dryer

White Mountain Bliss on 33 Acres

Killington ski house winter MTbike -new jacuzzi

Large Chalet; Sauna, Hot Tub; Walk to Trail

#45 Luxury Ski & Summer Condo with Private Sauna

Peaceful setting with Mountain Views
Family- and pet-friendly home rentals

Mid century modern gem with views of Sugarbush

The McKinley House

Mountain View Chalet near Jay Peak!

The Sunrise Cabin

Entire 2nd Floor Walk to Montpelier

The Sanctuary: 3 Bedrooms, Easy Walking, +Parking!

"Downtown" Norwich Apartment

Cheerful, cozy, close to outdoors
Family-friendly home rentals with a pool

1 Bedroom/1 Bath Cozy Condo @ Loon Mtn Lincoln,NH

Spacious Stowe condo Amzing views w/shared hot tub

Relax in Recreation Paradise!

Cozy, spacious, 3 bedrooms, 4 beds, 5 mi to K Rd.

White Mountains Ski and Golf Resort Home

EPIC Stowe Getaway - Great For Families & Friends

Large house, good for families, in Lincoln, NH

Spacious 4 Bdrm Townhouse Between Town & Mountain
Quick stats about vacation rentals that are family-friendly in Middlesex
Total rentals
70 properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
4.8K reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
70 properties include access to wifi
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- Sugarbush Resort
- Jay Peak Resort
- Smugglers' Notch Resort
- Spruce Peak
- Bolton Valley Resort
- Pico Mountain Ski Resort
- Jay Peak Resort Golf Course
- Cannon Mountain Ski Resort
- Pump House Indoor Waterpark
- Fort Ticonderoga
- Cochran's Ski Area
- Northeast Slopes Ski Tow
- Ethan Allen Homestead Museum
- Country Club of Vermont
- Dartmouth Skiway
- Mt. Eustis Ski Hill
- Cozy Cottages & Otter Valley Winery
- Burlington Country Club
- Autumn Mountain Winery
- Vermont National Country Club
- Lincoln Peak Vineyard
- Leahy Center for Lake Champlain
- Montshire Museum of Science
- Killington Adventure Center
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