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$205 per night from 13 Jul to 14 Jul
S$205
13 Jul - 14 Jul
includes taxes & fees
8.4/10 Very good! (92 reviews)
"Our stay was very relaxing and peaceful Location was good ..near the entertainment area. Maintenance needs to look into the drainage in the shower"

Reviewed on 13 Jun, 2026

Saba Arawak Hotel
El Momo Cottages

El Momo Cottages

3 out of 5
Booby Hill Windward Side Saba
8.6/10 Excellent! (57 reviews)
"Loved this place as so simply beautiful and relaxed. Not suitable if struggle with mobility as located up a steep hill / steps ... But worth the view."

Reviewed on 9 Mar, 2026

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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
10/10 Exceptional! (1 review)
"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.

Stay near popular Windward Side attractions

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.
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What to do in Windward Side

The Beauty of Fresh Lake Naivasha with some Cormorants Flying.

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

S$1,484
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$165
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.

Explore a world of travel with Expedia

* 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.