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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
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. Saba Deep Dive Center and Well's ...

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 Saba Deep Dive Center. ...

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. Saba Deep Dive ...

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 within 3 mi (5 km) of Saba Deep Dive Center, Well's Bay Beach, and Dutch Museum of Saba. Cove Bay Beach is 5.4 mi (8.6 ...

The Old Gin House

The Old Gin House

Oranjebaai 1, Oranjestad
3.0 out of 5.0

Situated on the beach, this hotel is steps from Lower Town Beach and Fort Oranje. Honem Dalim Synagogue Ruins and St. Eustatius Historical Foundation Museum ...

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 Dutch Reformed Church, The Quill, and Honem Dalim Synagogue Ruins. Also nearby are St. Eustatius ...

Top Flight Deals

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