Title: Windward Side Vacation Packages 2026 from $816 | Expedia.com [Windward Side Travel Guide](https://expedia.com/Windward-Side.dx11638)[Hotels in Windward Side](https://expedia.com/Windward-Side-Hotels.d11638.Travel-Guide-Hotels)[Vacation Rentals in Windward Side](https://expedia.com/Windward-Side-Vacation-Rentals.d11638.Travel-Guide-VacationRentals)[Flights to Windward Side](https://expedia.com/Cheap-Flights-To-Windward-Side.d11638.Travel-Guide-Flights)[Car Rentals in Windward Side](https://expedia.com/Car-Rentals-In-Windward-Side.d11638.Car-Rental-Guide) ![](https://images.trvl-media.com/place/11638/a9b7423c-b482-4cbc-b1e7-ef03e6886cb5.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Windward Side Vacations from $816 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## 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](https://www.expedia.com/Wells-Bay-Beach-Saba.d6114428.Vacation-Attraction), [Cove Bay Beach](https://www.expedia.com/Cove-Bay-Beach-Saba.d553248621584952177.Vacation-Attraction) and [Dutch Museum of Saba](https://www.expedia.com/Dutch-Museum-Of-Saba-Saba.d553248621584952178.Vacation-Attraction) 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. ## The Latest Windward Side vacation packages Price found within the past 48 hours. Click for updated prices. ![El Momo Cottages](https://images.trvl-media.com/lodging/12000000/11950000/11944600/11944556/33fcc0f7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### El Momo Cottages $816 per person Mar 20 - Mar 25 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Saba (SAB) 8.6/10 Excellent! (54 reviews) Was exactly as described, remote location with lots of stairs - well worth the walk, scenery was beautiful. Reviewed on Jul 20, 2025 Don't see what you're looking for? See all available trips from Columbus to Windward Side [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-07/2026-03-14/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SAB&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### Discover the most popular places to visit in Windward Side #### Saba Heritage Center You can spend an afternoon studying the exhibits at Saba Heritage Center in Windward Side. Wander the seaside and rainforest while you're in the area. [](https://expedia.com/Saba-Heritage-Center-Windward-Side.d808648223374106624.Vacation-Attraction) #### Harry L Johnson Museum You can spend an afternoon studying the exhibits at Harry L Johnson Museum in Windward Side. While you're in the area, wander around the gardens. [](https://expedia.com/Harry-L-Johnson-Museum-Windward-Side.d553248621533158269.Vacation-Attraction) ### What to do in Windward Side ![Edge Ferry to Saba](https://mediaim.expedia.com/localexpert/253604/6fc90e0a-d2d4-4d4b-ad5d-86cb5d90f28c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Edge Ferry Tickets to Saba $100 per adult **78%** of travellers recommend [](https://expedia.com/things-to-do/edge-ferry-tickets-to-saba.a253604.activity-details) ![Historic City and Beach E-Bike Tour](https://mediaim.expedia.com/localexpert/3327829/b5e8298c-321f-48e7-95c6-2e75bb8d85bb.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Historic City, Fort and Beach E-Bike Tour $130 per adult **100%** of travellers recommend [](https://expedia.com/things-to-do/historic-city.a3327829.activity-details) ![The Beauty of Fresh Lake Naivasha with some Cormorants Flying.](https://mediaim.expedia.com/localexpert/3421676/f8c19994-bd1e-40b1-9dd8-90b719267d98.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 5 Days Safari to Lake Naivasha, Hells Gate N/P, Maasai Mara N/R. $1,150 per adult [](https://expedia.com/things-to-do/5-days-safari-to-lake-naivasha.a3421676.activity-details) [See all activities in Windward Side](https://expedia.com/things-to-do/search?rid=11638) ## Windward Side Hotel Deals ![Saba Arawak Hotel](https://images.trvl-media.com/lodging/74000000/73670000/73660700/73660604/738de9aa_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Saba Arawak Hotel The peak Windward Side Saba $151 nightly $159 total Feb 8 - Feb 9 Total with taxes and fees 8.4/10 Very Good! (79 reviews) Friendly Staff Reviewed on Jan 7, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F8%2F2026&endDate=2%2F9%2F2026&selected=73660604&PinnedHotelID=73660604&HadPinnedHotel=true®ionId=11638) ![El Momo Cottages](https://images.trvl-media.com/lodging/12000000/11950000/11944600/11944556/33fcc0f7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### El Momo Cottages Booby Hill Windward Side Saba $116 nightly $122 total Feb 14 - Feb 15 Total with taxes and fees 8.4/10 Very Good! (54 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 [](https://expedia.com/Hotel-Search?startDate=2%2F14%2F2026&endDate=2%2F15%2F2026&selected=11944556&PinnedHotelID=11944556&HadPinnedHotel=true®ionId=11638) ![Flamboyant Cottage - Spectacular View & Pool](https://images.trvl-media.com/lodging/35000000/34010000/34006200/34006194/3c3130af_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Flamboyant Cottage - Spectacular View & Pool Windward Side Saba 9.6/10 Exceptional! (33 reviews) Lovely cabin with incredible view. Reviewed on Dec 19, 2025 [Get rates](https://expedia.com/Hotel-Search?startDate=2%2F21%2F2026&endDate=2%2F22%2F2026&selected=34006194&PinnedHotelID=34006194&HadPinnedHotel=true®ionId=11638) [](https://expedia.com/Hotel-Search?startDate=2%2F21%2F2026&endDate=2%2F22%2F2026&selected=34006194&PinnedHotelID=34006194&HadPinnedHotel=true®ionId=11638) [See all 27 properties in Windward Side](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F8%2F2026&endDate=2%2F9%2F2026®ionId=11638) 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. ## Find the Best Windward Side Vacation Packages ## Windward Side Essential Information | Closest Airport | Juancho E. Yrausquin Airport (SAB) | | --------------- | ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Population | 440 | | Max Temp Winter | 80ºF | | Max Temp Summer | 80ºF | | Top Sights | [Wells Bay Beach](https://www.expedia.com/Wells-Bay-Beach-Saba.d6114428.Vacation-Attraction), [Cove Bay Beach](https://www.expedia.com/Cove-Bay-Beach-Saba.d553248621584952177.Vacation-Attraction) and [Dutch Museum of Saba](https://www.expedia.com/Dutch-Museum-Of-Saba-Saba.d553248621584952178.Vacation-Attraction) | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations 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Yrausquin ](https://www.expedia.com/lp/airports/sab/flights-from-juancho-e-yrausquin-airport) - [Flights from Philipsburg (SXM) to Saba (SAB) ](https://www.expedia.com/lp/flights/sxm/sab/philipsburg-to-saba) - [Flights from Philadelphia (PHL) to Saba (SAB) ](https://www.expedia.com/lp/flights/phl/sab/philadelphia-to-saba) - [Flights from New York (JFK) to Saba (SAB) ](https://www.expedia.com/lp/flights/jfk/sab/new-york-to-saba) - [Flights from Miami (MIA) to Saba (SAB) ](https://www.expedia.com/lp/flights/mia/sab/miami-to-saba) - [Flights from San Juan (SJU) to Saba (SAB) ](https://www.expedia.com/lp/flights/sju/sab/san-juan-to-saba) - [Flights from Boston (BOS) to Saba (SAB) ](https://www.expedia.com/lp/flights/bos/sab/boston-to-saba) - [Flights from Chicago (ORD) to Saba (SAB) ](https://www.expedia.com/lp/flights/ord/sab/chicago-to-saba) - [Flights from Tampa (TPA) to Saba (SAB) ](https://www.expedia.com/lp/flights/tpa/sab/tampa-to-saba) - [Flights from Bonaire (BON) to Saba (SAB) ](https://www.expedia.com/lp/flights/bon/sab/bonaire-to-saba) - [Flights from Port of Spain (POS) to Saba (SAB) ](https://www.expedia.com/lp/flights/pos/sab/port-of-spain-to-saba) - [Flights from Denver (DEN) to Saba (SAB) ](https://www.expedia.com/lp/flights/den/sab/denver-to-saba) - [Flights from Tortola (EIS) to Saba (SAB) ](https://www.expedia.com/lp/flights/eis/sab/tortola-to-saba) - [Flights from Dallas (DFW) to Saba (SAB) ](https://www.expedia.com/lp/flights/dfw/sab/dallas-to-saba) - [Flights from Los Angeles (LAX) to Saba (SAB) ](https://www.expedia.com/lp/flights/lax/sab/los-angeles-to-saba) - [Flights to Juancho E. Yrausquin ](https://www.expedia.com/Cheap-Flights-To-Juancho-E-Yrausquin.d4342099.Travel-Guide-Flights) - [Flights from St. Thomas (STT) to Saba (SAB) ](https://www.expedia.com/lp/flights/stt/sab/st-thomas-to-saba) - [Flights from Detroit (DTW) to Saba (SAB) ](https://www.expedia.com/lp/flights/dtw/sab/detroit-to-saba) - [Flights from Atlanta (ATL) to Saba (SAB) ](https://www.expedia.com/lp/flights/atl/sab/atlanta-to-saba) - [Flights from Raleigh (RDU) to Saba (SAB) ](https://www.expedia.com/lp/flights/rdu/sab/raleigh-to-saba) - [Flights from Nashville (BNA) to Saba (SAB) ](https://www.expedia.com/lp/flights/bna/sab/nashville-to-saba) - [Flights from Oranjestad (AUA) to Saba (SAB) ](https://www.expedia.com/lp/flights/aua/sab/oranjestad-to-saba) - [Flights from Salt Lake City (SLC) to Saba (SAB) ](https://www.expedia.com/lp/flights/slc/sab/salt-lake-city-to-saba) - [Flights from New Orleans (MSY) to Saba (SAB) ](https://www.expedia.com/lp/flights/msy/sab/new-orleans-to-saba) - [Flights from New York (NYC) to Saba (SAB) ](https://www.expedia.com/lp/flights/nyc/sab/new-york-to-saba) - 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