Windward Side Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Stills 'n' stories
  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    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, 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.

Discover the most popular places to visit in Windward Side

What to do in Windward Side

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
8.4/10 Very Good! (60 reviews)
"Staff could be more friendly, but overall good"

Reviewed on Aug 3, 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

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

Flamboyant Cottage - Spectacular View & Pool
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.

More vacations you might like

Frequently asked questions

How much does a Windward Side vacation package cost?
You can pick up a vacation package to this destination 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.