Windward Side Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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Your Windward Side Vacation

Our Windward Side vacation packages give you the power to create your own adventure. Tailor your journey to suit your needs and interests and make every moment count in this wonderful city. Make your trip to Windward Side even more fun by going sightseeing. Wells Bay Beach, Cove Bay Beach and Dutch Museum of Saba are some of the major attractions you'll want to explore. Whoever you're going away with and whatever the size of your budget, your dream Windward Side vacation is just clicks away with Expedia.

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Windward Side Hotel Deals

Saba Arawak Hotel

Saba Arawak Hotel

3 out of 5
The peak, Windward Side, Saba
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Jul 30 to Jul 31
CA $159
CA $188 total
Jul 30 - Jul 31
includes taxes & fees
8.4/10 Very Good! (59 reviews)
"The staff are really frendly and kind but the bathroom is really dirty"

Reviewed on May 13, 2025

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 Jul. 20, 2025

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El Momo Cottages
Flamboyant Cottage - Spectacular View & Pool

Flamboyant Cottage - Spectacular View & Pool

Windward Side
9.6/10 Exceptional! (33 reviews)
Spectacular
"So lovely , whimsical, the view, the pool was so wonderful to cool off. Saba is magical.The cottage was clean and so many outdoor sitting spots.Could not recommend it more"

Reviewed on Mar. 18, 2025

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Flamboyant Cottage - Spectacular View & Pool
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

What to do in Windward Side

Historic City and Beach E-Bike Tour

Historic City, Fort and Beach E-Bike Tour

CA $178
per adult
Historic City, Fort and Beach E-Bike Tour
Edge Ferry to Saba

Edge Ferry Tickets to Saba

CA $137
per adult
76% of travellers recommend
Edge Ferry Tickets to Saba
The Beauty of Fresh Lake Naivasha with some Cormorants Flying.

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

CA $1,570
per adult
5 Days Safari to Lake Naivasha, Hells Gate N/P, Maasai Mara N/R.
See all activities in Windward Side

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. Travelling in quieter months means you'll typically find reduced prices on flights and hotels.
How many days is enough for Windward Side?
You can explore all the major sights in Windward Side within a few days, including the popular Mt Scenery. If you want a longer Windward Side vacation, check out what sort of day trips and activities are available in the area.
Is it worth booking a vacation package to Windward Side?
Whether you'd like to check out key attractions like Dutch Museum of Saba and Saba Heritage Centre 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 see and do, you'll soon learn why so many people think Windward Side is a good vacation destination.
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 travellers 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.

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