Photo by Meghan Watters

Hotels in Windward Side

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Where to stay in Windward Side?

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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Our prices for hotels in Windward Side are cheapest in October

See average prices and weather for all months

Price trends for hotels in Windward Side

Pricing is based on two traveler single night rates
Apr
$132
Average price during April is $132
May
$129
Average price during May is $129
Jun
$130
Average price during June is $130
Jul
$135
Average price during July is $135
Aug
$126
Average price during August is $126
Sep
$128
Average price during September is $128
Oct
$123
Average price during October is $123
Nov
$134
Average price during November is $134
Dec
$136
Average price during December is $136
Jan
$137
Average price during January is $137
Feb
$132
Average price during February is $132
Mar
$127
Average price during March is $127
Currently viewing crowd sizes and weather for April.

April

trending_flatModerate crowds
High 80°F / low 78°F. Sunny most days.
80°
weather_sun
April, Moderate crowds, average high temperature 80 degrees Fahrenheit, average low temperature 78 degrees Fahrenheit. Sunny most days.
78°
81°
weather_cloudy
May, Low crowds, average high temperature 81 degrees Fahrenheit, average low temperature 79 degrees Fahrenheit. Cloudy most days.
79°
82°
weather_sun
June, Low crowds, average high temperature 82 degrees Fahrenheit, average low temperature 80 degrees Fahrenheit. Sunny most days.
80°
83°
weather_sun
July, Low crowds, average high temperature 83 degrees Fahrenheit, average low temperature 81 degrees Fahrenheit. Sunny most days.
81°
83°
weather_sun
August, Low crowds, average high temperature 83 degrees Fahrenheit, average low temperature 81 degrees Fahrenheit. Sunny most days.
81°
84°
weather_sun
September, Moderate crowds, average high temperature 84 degrees Fahrenheit, average low temperature 81 degrees Fahrenheit. Sunny most days.
81°
84°
weather_cloudy
October, High crowds, average high temperature 84 degrees Fahrenheit, average low temperature 81 degrees Fahrenheit. Cloudy most days.
81°
82°
weather_cloudy
November, High crowds, average high temperature 82 degrees Fahrenheit, average low temperature 80 degrees Fahrenheit. Cloudy most days.
80°
80°
weather_sun
December, High crowds, average high temperature 80 degrees Fahrenheit, average low temperature 78 degrees Fahrenheit. Sunny most days.
78°
79°
weather_sun
January, Moderate crowds, average high temperature 79 degrees Fahrenheit, average low temperature 77 degrees Fahrenheit. Sunny most days.
77°
79°
weather_sun
February, Moderate crowds, average high temperature 79 degrees Fahrenheit, average low temperature 77 degrees Fahrenheit. Sunny most days.
77°
79°
weather_sun
March, High crowds, average high temperature 79 degrees Fahrenheit, average low temperature 77 degrees Fahrenheit. Sunny most days.
77°
Monthly weather averages (˚F)

Top landmarks in Windward Side

Learn more about Windward Side

Windward Side is applauded for its cultural attractions such as Dutch Museum of Saba and Saba Heritage Center. The city has something for everyone including sights like Mt Scenery and Harry L Johnson Museum within a scenic setting.

View from room at Juliana’s hotel. Super affordable and great views close to restaurants.
Photo by Meghan Watters
Open Photo by Meghan Watters
A tranquil hotel pool encircled by beautiful arches, enhancing the ambiance for leisure and relaxation.

Summer Getaway Sale

Save 25% or more on select hotels, and earn 50% more rewards on all properties. Book by May 26 and travel by Sep 30, 2025. See terms*

Frequently asked questions

What accommodations do travelers recommend in Windward Side?
El Momo Cottages is an accommodation that is popular with guests.
Where can I find free parking with my stay in Windward Side?
El Momo Cottages offers the perk of free parking.
Can I book refundable hotels in Windward Side?
If you’re looking for the flexibility to change your plans to Windward Side, most properties offer refundable* bookable rates. You can see these properties by searching our site and using the “fully refundable” filter to narrow down the results.
Where can I stay with my pet in Windward Side?
Your furry friend can stay with you at this pet-friendly hotel: El Momo Cottages.
Which Windward Side hotels do travelers like for their great location?
Our guests love Scout’s Place Hotel for its great location.
Where can I stay in Windward Side if I'm looking for a reasonably priced accommodation?
Scout’s Place Hotel is an accommodation you might want to consider that’ll save you money.
Where can I stay if I'm traveling to Windward Side for a family-friendly vacation?
Your kids are welcome at El Momo Cottages.
Where should I stay in Windward Side for a vacation with my partner?
El Momo Cottages is a good option for a romantic getaway with your special someone.
What will the weather in Windward Side be like during my visit?
Windward Side is a great place to visit any time of year with an average temperature of 78°F during the coldest months.
Why should I book my Windward Side hotel with Hotels.com?
There are lots of reasons to book your Windward Side trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

Terms and conditions

*Book by 5/26/2025 11:59 pm in hotel property local time. Stay between 4/17/2025-9/30/2025. Member Prices are available to Hotels.com® app users and One Key members. Limited availability, blackout periods may apply.

OneKeyCash is not redeemable for cash and can only be used on Hotels.com®, Expedia®, and Vrbo®.

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