Windward Side Vacations from $1,665
Book a Hotel + Flight or Car together to unlock savings
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.
The Latest Windward Side Vacation Packages
- El Momo Cottages
Jan 14 - Jan 19El Momo Cottages + Flight
Windward Side5 nights3.0 star property8.6/10 - Excellent (63 reviews)"Fun little place to stay at Saba. Not a traditional hotel, but each room is in it's own little cabin basically in a jungle with a patio and a bathroom. The jungle gets surprisingly loud at night and the morning views from our cabin were stunning. There is a lot of stairs everywhere around the property, so you'll have to be comfortable carrying your luggage and climbing the stairs up and down. Swimming pool was a very nice touch after a long day of hiking."Reviewed October 10, 2026Roundtrip • Boston (BOS) - Saba (SAB)BOS - EUX • 2 stops EUX - BOS • 2 stops$1,702$1,665found 1 day agoper traveler - Scenery Hotel Saba
Jan 14 - Jan 19Scenery Hotel Saba + Flight
Windward Side5 nights3.5 star propertyRoundtrip • Boston (BOS) - Saba (SAB)BOS - EUX • 2 stops EUX - BOS • 2 stops$2,634$2,372found 1 day agoper traveler
Where to stay in and around Windward Side
Oranjestad
Discover Oranjestad, a vibrant city perfect for travelers with a passion for culture and adventure who will appreciate its rich history and stunning natural beauty. With highlights like the St. Eustatius Historical Foundation Museum and the breathtaking landscapes of The Quill National Park, visitors can dive into local heritage and explore outdoor wonders. Located about 19 miles from Windward Side, Oranjestad is an ideal base for those seeking a mix of beach relaxation and thrilling activities, making it a smart choice for your stay.
The Bottom
Experience the charm of The Bottom, an excellent hub for eco-tourists and adventure seekers eager to explore the rich culture and stunning landscapes of Saba. Here, you can immerse yourself in activities like hiking up Mt. Scenery, relaxing at Well's Bay Beach, or discovering the Sulfur Mine. Located about 1 mile by car from Windward Side, The Bottom offers easy access to these attractions while providing a refreshing escape. Choosing to stay in The Bottom ensures a memorable island getaway.
Hell's Gate
Adventure seekers will love Hell's Gate, a vibrant destination known for its stunning landscapes and rich cultural experiences. Just a short drive from Windward Side, visitors can explore Mt. Scenery, relax at Cove Bay Beach, or discover the intriguing Sulfur Mine. With moderately seasonal traveler arrivals peaking from November to January, Hell's Gate offers a perfect blend of natural beauty and beach activities year-round. Choosing Hell's Gate for your stay ensures easy access to unforgettable experiences in Saba.
Upper Zion's Hill
Ideally situated for adventure seekers and eco-tourists, Upper Zion's Hill in Windward Side offers easy access to stunning attractions like Mt. Scenery, the beautiful Cove Bay Beach, and the historic Sulfur Mine. With a vibrant atmosphere that peaks from November to January, this village provides a unique blend of luxury and natural beauty. Booking a stay at Upper Zion's Hill ensures a memorable experience as you explore the enchanting landscapes of Saba.
Mount Scenery Trail
Looking for the perfect spot? Mount Scenery Trail in Windward Side is ideal for adventure seekers and eco-tourists eager to immerse themselves in nature. This picturesque area offers stunning views while providing access to local highlights like the majestic Mt Scenery, the Dutch Museum of Saba, and the Jo Bean Glass Art Studio. With its moderate visitor numbers, especially from November to January, Mount Scenery Trail is a smart choice for those wanting an enriching outdoor experience.
Discover the most popular places to visit in Windward Side
What to do in Windward Side
Historic City, Fort and Beach E-Bike Tour
5 Days Safari to Lake Naivasha, Hells Gate N/P, Maasai Mara N/R.
Windward Side Hotel Deals
"Excellent in all ways"
"mosquitos you had to climb 80 slippery steps to climb to reach to tiny room they call cottage one night strange voices of man and woman when i was told that only one or two people lived in mosquitoes bites whole body criquet sounds all night /cant sleep to reach toilet at night walk down 4 to 5 slippery steps in rain jungle like environment i was forced to leave after staying 3 nights and flnd better hotel and pay again for rest in Saba till 13 sept i complained to expedia customer...
"The room was nice, clean spacious but did not have a TV . Nice kitchen.The location is good , near the airport"
Quill Gardens Boutique Hotel
Quill Gardens Boutique Hotel"Anton was an excellent host. Best chef in town."
"It not a place that have amenities to enjoy. For rest and go it is ok."
Frequently Asked Questions
How much does a Windward Side vacation package cost?
You can pick up a vacation package to this destination from $1,665 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?
You can typically find lower prices and better availability in May, June and September. Take a look at our cheap Windward Side vacation packages and you could land some excellent off-season deals.
How many days is enough for Windward Side?
You can easily visit all the leading attractions in Windward Side in a few days, including the must-see Jo Bean Glass Art Studio. If you're after a longer Windward Side vacation, look at what kind of excursions and activities are available nearby.
Is it worth booking a vacation package to Windward Side?
Popular for its walking trails, underwater activities and nature, a Windward Side vacation is a hit with all kinds of travelers. Be sure to visit leading sights like Dutch Museum of Saba and Mt Scenery, and consider renting some wheels for day trips to discover even more.
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.
Does Expedia offer Book Now, Pay Later Windward Side vacation packages?
Your Windward Side break is meant to be an escape from your busy life, not a source of money worries. So to allow you extra flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.