Photo by Stills 'n' stories

Find Hotels with a Pool in Windward Side

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Windward Side Hotels with a Pool

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, (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, sun 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 ￥19,256
￥20,638 total
includes taxes & fees
Dec 14 - Dec 15
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, sun 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 ￥27,988
￥29,947 total
includes taxes & fees
Dec 19 - Dec 20
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.
View all properties

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 2 days 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 3 weeks ago
El Momo Cottages

Frequently asked questions

What are some accommodations with pools in Windward Side?
Saba Arawak Hotel: Features complimentary wired internet access, an outdoor pool, and free self parking. El Momo Cottages: Offers complimentary wireless internet access, an outdoor pool, and a restaurant. Flamboyant Cottage - Spectacular View & Pool: Provides complimentary wireless internet access, a pool, and kitchens. 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, check out 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 into account the local weather in Windward Side is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually September and October with an average temp of 83°F, while the coldest months are February and March with an average of 78°F. Average annual precipitation for Windward Side is 36 inches.