Photo by Meghan Watters

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Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Compare Resorts in Windward Side with updated reviews, rates, and availability.

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Other property types in Windward Side

Flamboyant Cottage - Spectacular View & Pool
Exterior

Flamboyant Cottage - Spectacular View & Pool

9.8 out of 10, Exceptional, (38)
"Our stay was perfect from the minute we landed on the island. Easy communication with property manager, taxi prearranged and the cottage had everything we needed! Great views, walking distance to town, restaurants and hiking. Everyone we met was SUPER friendly which made our stay extra special! "
Flamboyant Cottage - Spectacular View & Pool
Spyglass is a Private Villa With 360 View Near Windwardside.
Outdoor dining

Spyglass is a Private Villa With 360 View Near Windwardside.

9.8 out of 10, Exceptional, (67)
"We loved it here so much, we already booked it for Christmas next year. nuff said. "
Spyglass is a Private Villa With 360 View Near Windwardside.
Home a way from home in the Unspoiled queen of the Caribbean.
Exterior

Home a way from home in the Unspoiled queen of the Caribbean.

10.0 out of 10, Exceptional, (3)
"Even though we had to pay for an unused night on account of a canceled ferry, this was a beautiful place in a gorgeous location close to everything in Windwardside. My kids and I enjoyed the private pool with a view."
Home a way from home in the Unspoiled queen of the Caribbean.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

What can I expect from a resort vacation in Windward Side?
Expedia can help you browse resorts and other lodging options that have similar services and comforts. If you’re having trouble finding a resort in Windward Side that meets your needs, try using the search page filters to look for hotels, or search for properties with amenities like swimming pools or all-inclusive packages. We make it simple to book great accommodations so you can move on to creating your trip itinerary.
What's a top resort in Windward Side?
Our highest-rated resort near Windward Side: Queen’s Hotel Saba - 1 mi (1.6 km) from Windward Side. Features a terrace, a garden, and a bar.
What can I do in Windward Side?
If you’re interested in visiting some local museums, you can check out the exhibits at Dutch Museum of Saba and Saba Heritage Center. Mt Scenery and Harry L Johnson Museum are a few additional attractions in the area that you might like.
What's the weather like 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 the best way to get to and around Windward Side?
Fly into Saba (SAB-Juancho E. Yrausquin), which is located 1.3 mi (2.1 km) from the city center. Otherwise, look for flights into Oranjestad (EUX-F.D. Roosevelt), which is 19 mi (30.5 km) away. If you’d like to venture out around the area, consider renting a car to take in more sights.