Windward Side Vacation Packages
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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.
Top Windward Side Vacation Deals
Price found within the past 48 hours. Click for updated prices.
El Momo Cottages
Price was CA $1,434, price is now CA $1,402 per person
CA $1,402
per person
May 5 - May 8
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Saba (SAB)
8.6/10 Excellent! (57 reviews)
The staff is fantastic! Cabins are simple, clean and comfortable. Breakfast was delicious.The views are amazing! Be prepared to climb to enjoy the views. Lots of stairs but worth it!
Reviewed on Nov 21, 2025
Windward Side Hotel Deals
Saba Arawak Hotel
The peak Windward Side Saba
8.4/10 Very Good! (84 reviews)
It's on the windward side of the island...realize that!!!! Staff is really nice, the hike to "town" (no shops, few restaurants) is easy..
Reviewed on Mar 8, 2026
El Momo Cottages
Booby Hill Windward Side Saba
The price is CA $136 per night from Apr 10 to Apr 11
CA $136
CA $146 total
Apr 10 - Apr 11
includes taxes & fees
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 Mar 9, 2026
Spyglass is a Private Villa With 360 View Near Windwardside.
windwardside Saba
9.8/10 Exceptional! (69 reviews)
World Class experience
The villa is even more beautiful than the pictures. The views and gardens are even more vibrant and incredible than we expected. We were amazed at the incredible construction and attention to detail in the house. The building itself looks like much of the wood work and interior is custom built and ...
Reviewed on Mar 14, 2025
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.
What to do in Windward Side
5 Days Safari to Lake Naivasha, Hells Gate N/P, Maasai Mara N/R.
CA $1,576
per adult
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.
