Hotels with Pool & Resorts in Windward Side from AU$157

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Check availability on Windward Side Hotels with Pool

Our top choices for Windward Side hotels with a pool

Outdoor pool, pool loungers

Talk of the Town Inn & Suites

Talk of the Town Inn & Suites
3.0 star property
Oranjestad
9.2 out of 10, Wonderful, (13 reviews)
"Great location, nice people, clean."
Netherlands
Nadine
The price is AU$157
includes taxes & fees
16 Mar - 17 Mar
Talk of the Town Inn & Suites
Outdoor pool, pool loungers

The Old Gin House

The Old Gin House
3.0 star property
Oranjestad
8.4 out of 10, Very good, (60 reviews)
"Very awesome hotel, great history and staff was excellent, great job."
United States
Michael
The price is AU$275
includes taxes & fees
15 Mar - 16 Mar
The Old Gin House
Exterior

Quill Gardens Boutique Hotel

Quill Gardens Boutique Hotel
4.0 star property
Oranjestad
9.6 out of 10, Exceptional, (26 reviews)
"It was great time to stay with comfortable "
American Samoa
YONG
Quill Gardens Boutique Hotel
Outdoor pool

Saba Arawak Hotel

Saba Arawak Hotel
3.0 star property
Windward Side
8.4 out of 10, Very good, (84 reviews)
"Friendly Staff "
Canada
Trilochan
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, (57 reviews)
"Was exactly as described, remote location with lots of stairs - well worth the walk, scenery was beautiful."
Canada
Georgina
The price is AU$172
includes taxes & fees
15 Mar - 16 Mar
El Momo Cottages
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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Choose what matters most at hotels with a pool in Windward Side

Breakfast included
4 stars

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Top Windward Side Hotel Reviews

The Old Gin House

The Old Gin House

8/10 Good
"There is no shuttle. Someone at the airport got us a taxi. The hotel did not help in any way in us getting to the hotel. Important to know.....you are on your own to and from the hotel. Heads up hotel.com would not let me post this"
scott 3-night trip
Posted 3 days ago
The Old Gin House
El Momo Cottages

El Momo Cottages

10/10 Excellent
"Loved this place as so simply beautiful and relaxed. Not suitable if struggle with mobility as located up a steep hill / steps ... But worth the view. "
lucy 2-night trip
Posted 4 days ago
El Momo Cottages

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. El Momo Cottages: Offers complimentary wireless Internet access, an outdoor pool and laundry facilities. Spyglass is a Private Villa With 360 View Near Windwardside.: Features complimentary wireless Internet access, a pool and kitchens. Flamboyant Cottage - Spectacular View & Pool: Offers kitchens, a pool and televisions. Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!: Provides free self parking, an outdoor pool and complimentary wireless Internet access.
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, Harry L Johnson Museum and Jo Bean Glass Art Studio.
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.