Windward Side Vacations

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Find the Best Windward Side Vacation Packages

Windward Side Hotel Deals

El Momo Cottages

El Momo Cottages

3 out of 5
Booby Hill Windward Side Saba
8.6/10 Excellent! (58 reviews)
"Unique place overviewing the hills of Saba. Not a high class place to stay (in accordance with the rates), but everything is just good! Charming place, good service, good amenities, wonderful staff. I had a joyful stay and a great time!"

Reviewed on Jul 7, 2026

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El Momo Cottages
Flamboyant Cottage - Spectacular View & Pool

Flamboyant Cottage - Spectacular View & Pool

Windward Side Saba
9.8/10 Exceptional! (46 reviews)
"My husband and I had a great stay at Flamboyant Cottage. Before we arrived, the property manager had arranged for a taxi for us for both arrival and departure. The property manager met us at the cottage and took us grocery shopping right away, which made it very easy for us to choose between cooking ..."

Reviewed on Jun 3, 2026

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Flamboyant Cottage - Spectacular View & Pool
Peter Hytte is close to everything at great price!

Peter Hytte is close to everything at great price!

Windward Side Saba
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Peter Hytte is close to everything at great price!
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

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.
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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.

￥186,921
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

￥20,368
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 vacation package cost?
You can pick up a vacation package to this destination on Expedia. But how much your vacation 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 vacation package, consider visiting in April, June and July. You'll generally find better rates on accommodations 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 vacation. 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 vacation package to Windward Side?
Whether you're looking to check out attractions such as Dutch Museum of Saba and Saba Heritage Center on your Windward Side vacation, 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 vacation 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 vacation package well in advance.
Is it cheaper to book a Windward Side vacation as a package?
Expedia vacation 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 customized Windward Side vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation 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 favorite 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 customized Windward Side vacation package.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.