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Find Beach Hotels in Windward Side

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Check availability on Windward Side Beach Hotels

Tonight
Sep 30 - Oct 1
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Oct 1 - Oct 2
This weekend
Oct 3 - Oct 5
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Oct 10 - Oct 12

Top Windward Side Beach Hotels

El Momo Cottages
Outdoor pool, sun loungers

El Momo Cottages

3.0 star property
8.6 out of 10, Excellent, (54)
"Was exactly as described, remote location with lots of stairs - well worth the walk, scenery was beautiful."
El Momo Cottages
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, (69)
"This property is absolutely stunning! Views are amazing and just a really great place to stay. "
Spyglass is a Private Villa With 360 View Near Windwardside.
Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
Property grounds

Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!

10.0 out of 10, Exceptional, (11)
"Very pleased with the responsiveness of the owner, and location of the property. Exactly what we were looking for. Hope to stay again."
Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
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.
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Top Windward Side Hotel Reviews

El Momo Cottages

El Momo Cottages

10/10 Excellent
"Was exactly as described, remote location with lots of stairs - well worth the walk, scenery was beautiful."
Georgina 2-night trip
Posted 3 months ago
El Momo Cottages
The Old Gin House

The Old Gin House

10/10 Excellent
"hotel is close to town, at the ocean/beach, walkable and had good access to some nice options for lunch and diner, at hotel and nearby"
Erika 2-night trip
Posted 9 months ago
The Old Gin House

Frequently asked questions

What is Windward Side like for travelers who love the beach?
Find a great place to stay in Windward Side, which has a lot to offer the traveler looking to book a beach vacation.
When's the best time for a beach vacation in Windward Side?
Plan your trip to the beach with a look at year-round temperatures 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 is there to see and do around Windward Side?
After arriving and checking into your hotel, you'll probably want to explore your surroundings. If you're eager to check out the beaches, head to Well's Bay Beach or Cove Bay Beach for some relaxation by the water. Make time for a range of local attractions, which include Saba Heritage Center and Dutch Museum of Saba. For additional things to see and do, consider a visit to Mt Scenery or Harry L Johnson Museum.
What's the best way to get to my beach hotel in Windward Side?
Here's some information to help you get to and around your beach accommodation in Windward Side with ease. The closest major airport is Saba (SAB-Juancho E. Yrausquin), located 1.3 mi (2.1 km) from the city center. If you'd like to venture out around the area, you may want a rental car for your journey.