Windward Side Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Stills 'n' stories

Top hotels in Windward Side

Saba Arawak Hotel

Saba Arawak Hotel

3 out of 5
The peak, Windward Side, Saba
Fully refundableReserve now, pay when you stay
8.4/10 Very Good! (59 reviews)
"The staff are really frendly and kind but the bathroom is really dirty"

Reviewed on 13 May 2025

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Saba Arawak Hotel
El Momo Cottages

El Momo Cottages

3 out of 5
Booby Hill, Windward Side, Saba
8.4/10 Very Good! (54 reviews)
"Was exactly as described, remote location with lots of stairs - well worth the walk, scenery was beautiful."

Reviewed on 20 Jul 2025

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El Momo Cottages
The Cottage Club Hotel

The Cottage Club Hotel

3.5 out of 5
17a Grey Bush Street, Windward Side, Saba
"Beautiful views. Very centrally located and quiet."

Reviewed on 24 Nov 2021

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The Cottage Club Hotel
See all 29 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.

Popular places to visit

Saba Heritage Center

You can spend an afternoon browsing the exhibits at Saba Heritage Center in Windward Side. Wander the seaside and rainforest while you're in the area.

Saba Heritage Center

Jo Bean Glass Art Studio

You can spend an afternoon browsing the exhibits at Jo Bean Glass Art Studio during your trip to Windward Side. While you're in the area, wander around the gardens.

Jo Bean Glass Art Studio

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.