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 $2,147, price is now CA $2,135 per person
CA $2,135
per person
Jul 12 - Jul 19
found 18 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
The price is CA $185 per night from May 16 to May 17
CA $185
CA $217 total
May 16 - May 17
includes taxes & fees
8.4/10 Very Good! (88 reviews)
The room is decent, with a kitchen. The restaurant at the hotel ended their lease, so you need to go elsewhere for meals. It's a 5-10 minute walk into town. However the road is hilly and unlit, so I do not recommend walking at night.
Reviewed on May 7, 2026
El Momo Cottages
Booby Hill Windward Side Saba
The price is CA $123 per night from May 31 to Jun 1
CA $123
CA $133 total
May 31 - Jun 1
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
Flamboyant Cottage - Spectacular View & Pool
Windward Side Saba
9.8/10 Exceptional! (45 reviews)
We’ve had an amazing time in Flamboyant cottage. The location was perfect, great views, nice pool and walking distance to Windwardside. The service was great: from the pre-arranged taxi, welcome at check-in and the communication throughout our stay. Highly recommended when you’re looking for an unforgettable ...
Reviewed on May 8, 2026
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
Historic City, Fort and Beach E-Bike Tour
CA $180
per adult
100% of travellers recommend
5 Days Safari to Lake Naivasha, Hells Gate N/P, Maasai Mara N/R.
CA $1,583
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.
