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Hotels with Pool & Resorts in Windward Side from NZ$243

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Check availability on Windward Side Hotels with Pool

Tonight
30 Dec - 31 Dec
Tomorrow
31 Dec - 1 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Windward Side hotels with a pool

Outdoor pool
Saba Arawak Hotel

Saba Arawak Hotel

Saba Arawak Hotel
3.0 star property
Windward Side
8.4 out of 10, Very good, (75)
"Room was clean, great friendly staff especially Ahmad who welcomes everyone with big smile and is very helpful "
United States
shahzad
Saba Arawak Hotel
Outdoor pool, pool loungers
El Momo Cottages

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 NZ$255
includes taxes & fees
25 Jan - 26 Jan 2026
El Momo Cottages
Outdoor pool, pool loungers
Talk of the Town Inn & Suites

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 NZ$243
includes taxes & fees
1 Jan - 2 Jan 2026
Talk of the Town Inn & Suites
Outdoor pool
Quill Gardens Boutique Hotel

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

The Old Gin House
3.0 star property
Oranjestad
8.2 out of 10, Very good, (54)
"Staff was friendly. The property and surroundings were beautiful full of old Caribbean charm"
United States
James
The price is NZ$304
includes taxes & fees
4 Jan - 5 Jan 2026
The Old Gin House
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
"Staff was friendly. The property and surroundings were beautiful full of old Caribbean charm"
James 1-night trip
Posted 3 weeks ago
The Old Gin House
El Momo Cottages

El Momo Cottages

10/10 Excellent
"The staff is fantastic! Cabins are simple, clean and comfortable. Breakfast was delicious.The views are amazing! Be prepared to climb to enjoy the views. Lots of stairs but worth it!"
colin 3-night trip
Posted 2 months 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 a restaurant. 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 free self parking, an outdoor pool and complimentary wireless Internet access. The Cottage Club Hotel: Provides complimentary wireless Internet access, a pool and kitchens.
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 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.