Windward Side Vacations
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- Plan, book, travel with confidence
- Better togetherSave up to SAR 5,400 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Find the Best Windward Side Vacation Packages
Windward Side Hotel Deals
Saba Arawak Hotel
The peak Windward Side Saba
SAR 507
SAR 596 total
17 Oct - 18 Oct
includes taxes & fees
8.2/10 Very Good! (107 reviews)
"The restaurant was advertised as open, but was closed down when we arrived. They should also over a ride into town due to a dangerous road to walk there."
Reviewed on 5 October 2026
El Momo Cottages
Booby Hill Windward Side Saba
SAR 402
SAR 431 total
22 Oct - 23 Oct
includes taxes & fees
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 October 2026
Scenery Hotel Saba
9 Fort Street Windward Side Saba
SAR 785
SAR 939 total
24 Oct - 25 Oct
includes taxes & fees
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 browsing the exhibits at Dutch Museum of Saba in Windward Side. While you're in the area, wander around the gardens.
Saba Heritage Center
You can spend an afternoon studying the exhibits at Saba Heritage Center in Windward Side. Wander the seaside and rainforest while you're in the area.
Harry L Johnson Museum
8.8/10 (3 reviews)
You can spend an afternoon studying the exhibits at Harry L Johnson Museum in Windward Side. While you're in the area, wander around the gardens.
Jo Bean Glass Art Studio
9.8/10 (8 reviews)
You can spend an afternoon studying the exhibits at Jo Bean Glass Art Studio in Windward Side. While you're in the area, wander around the gardens.
Frequently asked questions
How much does a Windward Side vacation package cost?
You'll find cheap prices on Expedia for your Windward Side escape. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Windward Side costs.
What are the cheapest months to go to Windward Side?
April, June and July are the best times to search for cheap Windward Side vacation packages. Traveling in quieter months means you'll typically find reduced prices on flights and hotels.
How to find the best Windward Side package deals?
Use Expedia's filters to find some fabulous Windward Side package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Windward Side package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Windward Side vacation as a package?
You can enjoy significant savings on your next Windward Side break by booking a personalized vacation package. Click on the "Package" heading, then enter your destination and travel dates to view the best hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Windward Side?
If you have your Windward Side travel dates locked in, book early to grab some unbeatable deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Windward Side?
- Choose when to go: Check your calendar and get packing. Your preferred season and the activities available will also help you decide when to visit Windward Side.
- Plan your budget wisely: As well as the price of your accommodations, you'll need to factor in other expenses. These include transportation, food and flights. Also, put aside a little extra for unexpected costs that may crop up during your trip to Windward Side.
- Work out your trip length: Think about how long you'd like to spend exploring Windward Side. Plan your days so you can get to all the experiences and attractions you're interested in without rushing.
- Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to choose a Windward Side vacation package that brings all your bookings together.
