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Hotels with Pool & Resorts in Windward Side from AU$160

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Check availability on Windward Side Hotels with Pool

Tonight
8 Dec - 9 Dec
Tomorrow
9 Dec - 10 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Best Windward Side Hotels with Pool

Outdoor pool
Saba Arawak Hotel

Saba Arawak Hotel

3.0 star property
Windward Side
8.4 out of 10, Very good, (73)
"Room was cleaned everyday and the staff I met was very courteous. Thanks Saba Arawak Hotel"
United States
Velmarie
Saba Arawak Hotel
Outdoor pool, pool loungers
El Momo Cottages

El Momo Cottages

3.0 star property
Windward Side
8.6 out of 10, Excellent, (55)
"Was exactly as described, remote location with lots of stairs - well worth the walk, scenery was beautiful."
Canada
Georgina
The price is AU$160
includes taxes & fees
9 Dec - 10 Dec
El Momo Cottages
Outdoor pool
Quill Gardens Boutique Hotel

Quill Gardens Boutique Hotel

4.0 star property
Oranjestad
9.6 out of 10, Exceptional, (22)
"It was great time to stay with comfortable "
American Samoa
YONG
Quill Gardens Boutique Hotel
Outdoor pool, pool loungers
The Old Gin House

The Old Gin House

3.0 star property
Oranjestad
8.2 out of 10, Very good, (53)
"Spacious room with a fabulous view. Friendly staff, convenient location. "
United States
Rosalynn
The price is AU$290
includes taxes & fees
11 Dec - 12 Dec
The Old Gin House
Outdoor pool, pool loungers
Talk of the Town Inn & Suites

Talk of the Town Inn & Suites

3.0 star property
Oranjestad
9.0 out of 10, Wonderful, (12)
"pleasant & enjoyable, clean."
United States
Donovan
The price is AU$226
includes taxes & fees
1 Jan - 2 Jan 2026
Talk of the Town Inn & Suites
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

The Old Gin House

The Old Gin House

10/10 Excellent
"Old Gin House has a great location. It is a 10 minute walk to the ferry terminal. The best dive shop on the island is across the street from the hotel. You can walk across the street to the beach for swimming and snorkeling. Food in the hotel restaurant is good."
Larry 4-night trip
Posted 7 days ago
The Old Gin House

Frequently asked questions

What are some accommodation options with pools in Windward Side?
Saba Arawak Hotel: Features complimentary high-speed (wired) Internet access, an outdoor pool and free self parking. Flamboyant Cottage - Spectacular View & Pool: Offers complimentary wireless Internet access, a pool and kitchens. El Momo Cottages: Provides complimentary wireless Internet access, an outdoor pool and laundry facilities. Spyglass is a Private Villa With 360 View Near Windwardside.: Features free self parking, an outdoor pool and complimentary wireless Internet access. Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!: Offers kitchens, a pool and televisions.
What is there to see and do in Windward Side?
Take in the natural beauty with a stop at Mt Scenery. During your stay, visit sights such as Dutch Museum of Saba, Saba Heritage Center and Harry L Johnson Museum.
When is the best time to book a hotel with a pool in Windward Side?
Taking the local weather in Windward Side into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. 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.