Kid-friendly holiday rentals in Windsor County

Find and book unique family-friendly rentals on Airbnb

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Popular amenities for Windsor County family-friendly rentals

Family-friendly apartment rentals

Guest favourite

Apartment in Ludlow

4.92 out of 5 average rating, 122 reviews

All Season Lovely and Zen Okemo Mt Lodge Condo

12–19 May

£95 per night
Guest favourite

Apartment in Killington

4.81 out of 5 average rating, 140 reviews

1BR Modern Condo @ Whiffletree Ground Fl Walkout

16–23 May

£93 per night
Guest favourite

Apartment in Killington

4.89 out of 5 average rating, 203 reviews

Killington-Pico ski in/out Studio at base of Pico

14–21 May

£100 per night
Guest favourite

Apartment in Killington

4.93 out of 5 average rating, 181 reviews

Newly renovated ski retreat at Killington

7–14 May

£120 per night
Guest favourite

Apartment in Ludlow

4.99 out of 5 average rating, 100 reviews

Updated Main St Condo in downtown Ludlow!

4–11 Jun

£109 per night
Guest favourite

Apartment in Killington

4.87 out of 5 average rating, 149 reviews

⛷☃️Close to lifts. Rustic. Mountain Green Resort🏂❄️…

19–26 May

£151 per night
Guest favourite

Apartment in Killington

4.94 out of 5 average rating, 152 reviews

Bright Ski on/off Condo Full Kitchen-Free Shuttle!

28 Jun – 5 Jul

£151 per night
Guest favourite

Apartment in Killington

4.94 out of 5 average rating, 174 reviews

Walk or Shuttle to Lifts/2BR @ Mt. Green Resort

26 Aug – 2 Sept

£191 per night

Destinations to explore