Photo by Meghan Watters

Beach Hotels & Resorts in Windward Side

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Check availability on Windward Side Beach Hotels

Tonight
29 Jul - 30 Jul
Tomorrow
30 Jul - 31 Jul
This weekend
1 Aug - 3 Aug
Next weekend
8 Aug - 10 Aug

Best Windward Side Beach Hotels

El Momo Cottages
Outdoor pool, pool loungers

El Momo Cottages

3.0 star property
8.6 out of 10, Excellent, (54)
"Loved my stay at El Momo! It's rustic and a climb up the 60 steps, but the views are amazing, Andries was helpful and welcoming, and it's SO peaceful. Definitely not a chain hotel, but if you're looking for a quiet, quaint cottage and don't mind a frog or gecko passing through - it's wonderful! The Sunshine cottage has a shower overlooking the ocean and was perfect!"
Dana
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, (68)
"This property is absolutely stunning! Views are amazing and just a really great place to stay. "
Wendy N.
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)
"Amazing cottage. We canceled our plans in Philipsburg to spend 5 nights on Saba. Great choice! The island is incredible and this cottage in Windwardside was perfect for us. We enjoyed world-class scuba diving with
Sea
Saba. Easy walk to bakery, markets, bars and restaurants. Near several hiking trails. We did not rent a car and did not need one. Excellent host! Highly recommend!"
Dale
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.

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 9 days 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 7 months ago
The Old Gin House

Frequently asked questions

What is Windward Side like for travellers who love the beach?
Find a great place to stay in Windward Side, which has a lot to offer the traveller looking to book a beach holiday.
What's the best hotel to stay near the beach in Windward Side?
Scout's Place Hotel is a top hotel with free continental breakfast and free WiFi, and it's located close to Cove Bay Beach . Other good choices to stay near the beach include Juliana's Hotel and El Momo Cottages.
How many beach hotels are there in Windward Side?
Expedia has 8 beach hotels in Windward Side that are great for your beachside getaway.
When's the best time for a beach holiday 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 temperature of 28°C, while the coldest months are February and March, with an average of 26°C. Average annual precipitation for Windward Side is 921 mm.
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 Cove Bay Beach or Well's 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 in Saba (SAB-Juancho E. Yrausquin), located 1.3 mi (2.1 km) from the city centre. If you'd like to venture out around the area, you may want to rent a car for your trip.