Windward Side Holidays

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Top hotels in Windward Side

Saba Arawak Hotel

Saba Arawak Hotel

3 out of 5
The peak Windward Side Saba
The price is S$204 per night from 16 Nov to 17 Nov
S$204
16 Nov - 17 Nov
includes taxes & fees
8.2/10 Very good! (112 reviews)
"this hotel is located close to everything in Windward side. just a 10 minute stroll to the main area with the restaurants, bakery, shops, souvenirs, church, gym and tourism office. you really do not need a car if you stay here. just be mindful when walking"

Reviewed on 13 Nov, 2026

Saba Arawak Hotel
El Momo Cottages

El Momo Cottages

3 out of 5
Booby Hill Windward Side Saba
8.6/10 Excellent! (63 reviews)
"Fun little place to stay at Saba. Not a traditional hotel, but each room is in it's own little cabin basically in a jungle with a patio and a bathroom. The jungle gets surprisingly loud at night and the morning views from our cabin were stunning. There is a lot of stairs everywhere around the property, ..."

Reviewed on 10 Oct, 2026

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El Momo Cottages
Scenery Hotel Saba

Scenery Hotel Saba

3.5 out of 5
9 Fort Street Windward Side Saba
The price is S$392 per night from 22 Nov to 23 Nov
S$392
22 Nov - 23 Nov
includes taxes & fees
Scenery Hotel Saba
See all 30 properties 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.

Stay near popular Windward Side attractions

Dutch Museum of Saba

8.4/10 (5 reviews)
You can spend time studying the exhibits at Dutch Museum of Saba during your travels in Windward Side. While you're in the area, wander around the gardens.
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What to do in Windward Side

5 Days Safari to Lake Naivasha, Hells Gate N/P, Maasai Mara N/R.

5 Days Safari to Lake Naivasha, Hells Gate N/P, Maasai Mara N/R.

S$1,469
per adult
5 Days Safari to Lake Naivasha, Hells Gate N/P, Maasai Mara N/R.
Historic City and Beach E-Bike Tour

Historic City, Fort and Beach E-Bike Tour

S$166
per adult
100% of travellers recommend
Historic City, Fort and Beach E-Bike Tour
See all activities in Windward Side

Frequently asked questions

How much does a Windward Side holiday package cost?
You can pick up a holiday package to this destination on Expedia. But how much your holiday to Windward Side costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Windward Side?
If you're looking to snag a cheap Windward Side holiday package, consider visiting in April, June and July. You'll generally find better rates on accommodation and flights during these months — perfect for a budget-friendly getaway.
How many days is enough for Windward Side?
Typically, a few days is enough for a Windward Side holiday. With a carefully crafted itinerary, you can visit all the popular attractions like Harry L Johnson Museum, as well as explore some hidden gems along the way.
Is it worth booking a holiday package to Windward Side?
Whether you're looking to check out attractions such as Dutch Museum of Saba and Saba Heritage Centre on your Windward Side holiday, or coming for its great walking trails, nature and underwater activities, there's something for everyone here. With so much to experience, you'll soon discover why so many visitors think Windward Side is a good holiday destination.
How to find the best Windward Side package deals?
Use Expedia's filter tool to help you find some fabulous Windward Side package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Windward Side package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your holiday package well in advance.
Is it cheaper to book a Windward Side holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component separately. And you'll still have the flexibility to create a customised Windward Side holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday package to Windward Side?
Land incredible bargains by booking your flights early with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Windward Side getaway.
How to plan a trip to Windward Side?

  1. Choose when to travel: Check your calendar and pack your bags. Your favourite time of year and the type of activities on offer will also help you decide when to visit Windward Side.
  2. Budget wisely: On top of the price of your hotel, you'll need to consider other expenses. These include food, flights and transportation. Also, put aside a little extra for unexpected costs that could arise during your trip to Windward Side.
  3. Determine how many days away: Start by listing all the attractions you'd like to get to in Windward Side. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a customised Windward Side holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.