Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Windward Side Vacations

Pack those stellar shades. We have Windward Side vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Windward Side – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Windward Side vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Windward Side

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Windward Side vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Windward Side well.

Top Hotel Deals

See all 6 Hotels in Windward Side
El Momo Cottages

El Momo Cottages

Booby Hill, Windward Side
    2.5 out of 5.0

    Situated in Windward Side, this guesthouse is 0.3 mi (0.5 km) from Dutch Museum of Saba and within 6 mi (10 km) of Cove Bay Beach and Well's Bay Beach.

    Selera Dunia Boutique Hotel

    Selera Dunia Boutique Hotel

    Wall Street, Windward Side
      3.0 out of 5.0

      Located in the heart of Windward Side, this bed & breakfast is 0.1 mi (0.2 km) from Dutch Museum of Saba and 2.9 mi (4.6 km) from Cove Bay Beach. Well's Bay ...

      Scout's Place Hotel

      Scout's Place Hotel

      Windwardside, Windward Side
        2.5 out of 5.0

        Situated near the airport, this hotel is 0.1 mi (0.1 km) from Dutch Museum of Saba and 2.9 mi (4.7 km) from Cove Bay Beach. Well's Bay Beach is 3.8 mi (6.2 km) ...

        The Old Gin House

        The Old Gin House

        Oranjebaai 1, Oranjestad
          3.0 out of 5.0

          Nestled on the beach, this Oranjestad hotel is within a 10-minute walk of Lower Town Beach, Fort Oranje, and Honem Dalim Synagogue Ruins. St. Eustatius Historical ...

          Queen's Garden Resort & Spa

          Queen's Garden Resort & Spa

          Troy Hill #1, The Bottom
            4.0 out of 5.0

            Situated near the bay, this spa resort is 2.1 mi (3.4 km) from Well's Bay Beach and 2.6 mi (4.1 km) from Dutch Museum of Saba. Cove Bay Beach is 5.4 mi (8.6 ...

            Palm Spring Inn

            Palm Spring Inn

            Erick R Gibbs Road 2, Oranjestad
              3.0 out of 5.0

              Situated in Oranjestad, this apartment building is close to Honem Dalim Synagogue Ruins, St. Eustatius Historical Foundation Museum, and Fort Oranje. Nearby ...

              Top Flight Deals

              Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.