Family-friendly vacation rentals in Winhall
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Winhall
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 Winhall family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Plymouth
4.95 out of 5 average rating, 237 reviewsTop of the World! Jacuzzi! Private Hiking Trails!
Home in Colrain
4.93 out of 5 average rating, 167 reviewsSecluded Farmhouse Retreat - stunning views
Chalet in Ludlow
4.95 out of 5 average rating, 118 reviewsOkemo Ski Chalet with Hot Tub
Home in Cavendish
4.84 out of 5 average rating, 141 reviewsOkemo-Ludlow, fireplace, hottub, sleeps 13
Home in Newfane
4.98 out of 5 average rating, 130 reviewsPeaceful cabin close to skiing & Brattleboro
Home in Ludlow
4.97 out of 5 average rating, 151 reviewsSki Chalet with Hot Tub on Okemo Mountain
Home in Argyle
4.83 out of 5 average rating, 150 reviewsExpansive Lakehouse with Jacuzzi
Loft in Ludlow
4.95 out of 5 average rating, 774 reviewsSpacious Renovated Barn Apt on 100 acres!
Family- and pet-friendly home rentals
Cabin in West Windsor
4.97 out of 5 average rating, 132 reviewsCowshed Cabin Farm
Cabin in Shaftsbury
4.9 out of 5 average rating, 400 reviewsThe LoveNest -Charming private cabin on 65 acres
Cabin in Cavendish
4.96 out of 5 average rating, 145 reviewsThe Cozy Little Red Cabin
Loft in Wilmington
4.93 out of 5 average rating, 187 reviewsWalk to Village/Lake Whitingham
Cabin in Woodford
4.84 out of 5 average rating, 361 reviews400+ Airbnb Visits: Incredible Mountain Cabin
Rental unit in Town of Rockingham
4.82 out of 5 average rating, 172 reviewsApartment on Main Street
Home in Mt Tabor
4.92 out of 5 average rating, 179 reviewsNow thru Dec 15th 140.00
Home in Readsboro
4.86 out of 5 average rating, 124 reviewsRelax in Peaceful Vermont! (Pet Friendly)
Family-friendly home rentals with a pool
Home in Salem
4.98 out of 5 average rating, 185 reviewsMagical Farm Getaway - a must visit!
Townhouse in Dover
4.96 out of 5 average rating, 143 reviewsBear's Den - Mt Snow Townhome w/ Ski Home Trail!
Home in Manchester
4.82 out of 5 average rating, 51 reviewsPerfect reunion house! Pool, tennis, fireplac, dog
Condo in Dover
4.87 out of 5 average rating, 228 reviewsMt Snow Ski In/Out at Seasons
Home in Newfane
4.92 out of 5 average rating, 48 reviews6 BR Perfect Private Retreat in Vermont!
Townhouse in Dover
4.93 out of 5 average rating, 76 reviewsCozy Bear- 1 mile to Mt Snow Ski Home
Condo in Ludlow
4.91 out of 5 average rating, 85 reviewsOne Bedroom Suite Near Okemo
Bungalow in Williamstown
4.89 out of 5 average rating, 211 reviewsHollywood Bungalow in the Berkshires
Quick stats about vacation rentals that are family-friendly in Winhall
Total rentals
260 properties
Nightly prices starting at
$110 before taxes and fees
Total number of reviews
6.8K reviews
Pet-friendly rentals
100 properties allow pets
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
140 properties have a dedicated workspace
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