Family-friendly holiday 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.
Holiday 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
Cabin in Londonderry
4.82 out of 5 average rating, 421 reviewsThe Honeymoon Barn - hot tub/sauna #1 Airbb S. VT
25 Jan – 1 Feb
Home in Shaftsbury
4.93 out of 5 average rating, 122 reviewsConverted Vermont Barn on 6.5 acres with hot tub
6–13 Sep
Home in Newfane
4.97 out of 5 average rating, 114 reviewsPeaceful cabin close to skiing & Brattleboro
9–16 Jan
Loft in Ludlow
4.95 out of 5 average rating, 735 reviewsSpacious Renovated Barn Apt on 100 acres!
31 Dec – 7 Jan
Home in Ludlow
4.97 out of 5 average rating, 147 reviewsSki Chalet with Hot Tub on Okemo Mountain
10–17 Jul
Home in Dover
4.98 out of 5 average rating, 125 reviewsOutdoor Paradise - Private Jacuzzi & Sauna
6–13 Sep
Home in Argyle
4.83 out of 5 average rating, 145 reviewsExpansive Lakehouse with Jacuzzi
28 Oct – 4 Nov
Home in Colrain
4.94 out of 5 average rating, 155 reviewsSecluded Farmhouse Retreat - stunning views
22–29 Dec
Family- and pet-friendly home rentals
Apartment in Cambridge
4.91 out of 5 average rating, 369 reviewsWake up to spectacular views!
7–14 Apr
Home in Weston
4.95 out of 5 average rating, 227 reviewsReillys Rest -GreenMtns! Secluded-Pet-Kid friendly
13–20 Sep
Home in Danby
4.97 out of 5 average rating, 198 reviewsComfortable farmhouse with stunning views
10–17 Sep
Home in Manchester
4.87 out of 5 average rating, 247 reviewsManchester Center with Mt. Equinox View / In Town
23–30 Sep
Cabin in Shaftsbury
4.9 out of 5 average rating, 381 reviewsThe LoveNest -Charming private cabin on 65 acres
16–23 Jan
Cabin in Brattleboro
4.89 out of 5 average rating, 442 reviewsCottage
3–10 Jul
Apartment in Newfane
4.97 out of 5 average rating, 406 reviewsRock River Retreat: Pets Welcome
14–21 Feb
Cabin in Jamaica
4.88 out of 5 average rating, 264 reviewsGreen Mountain Modern House: iconic modern getaway
6–13 Mar
Family-friendly home rentals with a pool
Home in Wilmington
4.9 out of 5 average rating, 130 reviews4 bedroom Ski House 15 min to Mount Snow
12–19 Jan
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
4–11 Dec
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
8–15 Sep
Home in Salem
4.98 out of 5 average rating, 180 reviewsMagical Farm Getaway - a must visit!
12–19 Apr
Home in Wilmington
4.83 out of 5 average rating, 155 reviewsThe Vermont Barn (Mount Snow)
10–17 Feb
Townhouse in Dover
4.96 out of 5 average rating, 136 reviewsBear's Den - Mt Snow Townhome w/ Ski Home Trail!
13–20 Nov
Condo in Dover
4.87 out of 5 average rating, 222 reviewsMt Snow Ski In/Out at Seasons
29 Sep – 6 Oct
Home in Londonderry
4.83 out of 5 average rating, 53 reviewsDeer Hill, With a Pool and Central HVAC system
7–14 Jun
Quick stats about holiday rentals that are family-friendly in Winhall
Total rentals
270 properties
Rentals with dedicated workspaces
140 properties have a dedicated workspace
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
100 properties allow pets
Total number of reviews
6.4K reviews
Nightly prices starting at
$202 NZD before taxes and fees
Destinations to explore
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