Photo by Meghan Watters

Beach Hotels & Resorts in Windward Side from AU$163

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Best Windward Side Beach Hotels

El Momo Cottages

3.0 star property
8.6 out of 10, Excellent, (47)
"I had a wonderful visit at El Momo. I was in Saba for hiking and the cottages were nestled into the woods, giving the perfect setting for enjoying the natural surroundings. The view from the cottages was amazing, the pool was a perfect spot to relax after a day out. The staff was helpful and friendly. "
The price is AU$163
includes taxes & fees
9 Dec - 10 Dec
El Momo Cottages

Spyglass is a Private Villa With 360 View Near Windwardside.

9.8 out of 10, Exceptional, (64)
"We absolutely loved our week at Spyglass! The home has the feel of a traditional Saba cottage, with some of the BEST views in the Caribbean. We love this small island. The hiking is amazing, the diving is world class, and we love the local food. The home is in a private location, very peaceful and quiet. We would definitely choose to stay here again. If you lead an active lifestyle and enjoy walking/hiking, you can easily walk to the main areas in the village of Windwardside where the local...
Spyglass is a Private Villa With 360 View Near Windwardside.

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

10.0 out of 10, Exceptional, (10)
"The people of Saba are very friendly. This location has many fantastic restaurant choices within a short walk. Our host Jeffery was wonderful. Very helpful. Because he lives next door he's always available. The cottage was roomy for the 2 of us. WiFi worked great and there's plenty of electrical outlets (American Style 110 volt). I can say enough nice things about this rental."
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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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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 Jo Bean Glass Art Studio. For additional things to see and do, consider a visit to Dutch Museum of Saba 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.