Photo by Meghan Watters

Find Family Hotels in Windward Side

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare Windward Side Family Hotels room rates, reviews, and availability. Most hotels are fully refundable.

Frequently asked questions

What's Windward Side like for family-friendly vacations?
The destination of Windward Side is a great choice if you’ve been thinking about a vacation with your kids. The diving, hiking trails, and scuba diving are just a few things that make this a great choice for a family vacation. Arrange a flight into Saba (SAB-Juancho E. Yrausquin), which is the closest airport, or Oranjestad (EUX-F.D. Roosevelt), which is located 19 mi (30.5 km) from the city center.
What's the best hotel for a family trip to Windward Side?
El Momo Cottages is a guesthouse with an outdoor pool and a restaurant, and it’s a top choice on Expedia for families.
How many hotels that welcome families can I expect to find in Windward Side?
Expedia has 6 family-friendly hotels and other accommodations in Windward Side.
When's the best time to book a family-friendly vacation in Windward Side?
The hottest months are usually September and October with an average temp of 83°F, while the coldest months are February and March with an average of 78°F. Average annual precipitation for Windward Side is 36 inches.
What's there to see and do with your family in Windward Side?
While you and the family are vacationing in Windward Side, you might want to check out some of the attractions here such as Jo Bean Glass Art Studio, Mt Scenery, and Cove Bay Beach. Make sure you have lots of time for activities like Well’s Bay Beach and Sulfur Mine.