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Hotels in Windward Side

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Check Last Minute Windward Side Hotel Deals

Tonight Apr 26 - Apr 27This weekend Apr 26 - Apr 28

Last Minute Hot Rate® Hotel Deals in Windward Side

We Hide Hotel Names So You Can Find 4-Star Hotels At 2-Star Prices. Choose the Location, Star Rating & Amenities. Let Hotwire Find You the Best Deal. Book Today!

Hot Rate® Hotel

3.5-star Hotel in Saint Kitts
3.5 out of 5

3.5-star Hotel

in Saint Kitts
38 miles from Windward Side
$79
per night
$98 total
incl. taxes & fees
3.5-star Hotel in Saint Kitts

Hot Rate® Hotel

4-star Hotel in Saint Kitts
4 out of 5

4-star Hotel

in Saint Kitts
38 miles from Windward Side
$149
per night
$167 total
incl. taxes & fees
4-star Hotel in Saint Kitts

Hot Rate® Hotel

3.5-star Hotel in Sint Maarten
3.5 out of 5

3.5-star Hotel

in Sint Maarten
30 miles from Windward Side
$189
per night
$223 total
incl. taxes & fees
3.5-star Hotel in Sint Maarten

Hot Rate® Hotel

4-star Hotel in Sint Maarten
4 out of 5

4-star Hotel

in Sint Maarten
30 miles from Windward Side
$199
per night
$261 total
incl. taxes & fees
4-star Hotel in Sint Maarten
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Choose from 27 Windward Side Hotel Deals

El Momo Cottages
El Momo Cottages
3 out of 5
Booby Hill, Windward Side, Saba
  • 3 min walk from Dutch Museum of Saba
The price is $99 per night from Apr 27 to Apr 28
$99
per night
Apr 27 - Apr 28
Stay at this 3-star guesthouse in Windward Side. Enjoy free WiFi, breakfast, and a terrace. Popular attractions Dutch Museum of Saba and Saba Heritage Center ...
8.4/10 Very Good! (44 reviews)
"We had a great weekend in Saba. The owners were very nice and welcoming and the cottages were comfortable. Near lovely restaurants and shops, and close to the trails. Breakfast was great and pool refreshing. Only downside was the noise at night from neighborhood dogs barking and early roosters. We ..."

Reviewed on Apr 9, 2024

El Momo Cottages
Saba Arawak Hotel
Saba Arawak Hotel
3 out of 5
The peak, Windward Side, Saba
  • 1 min walk from Dutch Museum of Saba
The price is $129 per night from Apr 27 to Apr 28
$129
per night
Apr 27 - Apr 28
Stay at this 3-star business-friendly hotel in Windward Side. Enjoy free WiFi, free parking, and breakfast. Popular attractions Dutch Museum of Saba and Saba ...
8.4/10 Very Good! (28 reviews)
"I selected this property because of how close it is to hiking trails. This is perfect if that’s why you’re visiting the island. It is also close to a supermarket and plenty of restaurants. I didn’t have any issues with wifi at all which seems to be complaints from previous guests. Overall I had a ..."

Reviewed on Mar 6, 2024

Saba Arawak Hotel
Selera Dunia Boutique Hotel
Selera Dunia Boutique Hotel
3 out of 5
Wall Street, Windward Side, Saba
  • 2 min walk from Dutch Museum of Saba
Stay at this 3-star business-friendly B&B in Windward Side. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Harry L Johnson Museum and ...
9.2/10 Wonderful! (76 reviews)
"Hemmie is one of the best hosts I’ve ever met! He made me feel so at home from day 1. I was on the island for an exam and Hemmie made my stay less stressful by serving delicious breakfast every morning and offering to give me free dinner. He even offered to drive me to and from school, which was ..."

Reviewed on Aug 15, 2023

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Selera Dunia Boutique Hotel
The Cottage Club Hotel
The Cottage Club Hotel
3.5 out of 5
17a Grey Bush Street, Windward Side, Saba
  • 2 min walk from Dutch Museum of Saba
Stay at this 3.5-star hotel in Windward Side. Enjoy free WiFi, free parking, and a terrace. Popular attractions Harry L Johnson Museum and Jo Bean Glass Art ...
10/10 Exceptional! (1 review)
"Beautiful views. Very centrally located and quiet."

Reviewed on Nov 24, 2021

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The Cottage Club Hotel
The Old Gin House Hotel
The Old Gin House Hotel
3 out of 5
Oranjebaai 1, Oranjestad, Sint Eustatius
  • 27 min drive from Dutch Museum of Saba
The price is $185 per night from May 4 to May 5
$185
per night
May 4 - May 5
Stay at this 3-star beach hotel in Oranjestad. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Fort Oranje and Lower Town Beach are located ...
8.2/10 Very Good! (40 reviews)
"The new owners are working hard to refresh this historic property. The seaside location is a gem and the staff members are friendly and attentive (special shout-out to Julia). The full breakfast is a wonderful benefit, and my mahi-mahi dinner was absolutely delicious! An added bonus is the proximity ..."

Reviewed on Apr 16, 2024

The Old Gin House Hotel
Quill Gardens Boutique Hotel
Quill Gardens Boutique Hotel
4 out of 5
Road to English Quarter, Oranjestad, Sint Eustatius
  • 26 min drive from Dutch Museum of Saba
The price is $183 per night from Apr 27 to Apr 28
$183
per night
Apr 27 - Apr 28
Stay at this 4-star business-friendly guesthouse in Oranjestad. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Government Guesthouse ...
9/10 Wonderful! (13 reviews)
"Second stay at this gem of a property. If you are looking for a quiet relaxing place to stay while you hike Statia, this is your spot."

Reviewed on Mar 2, 2024

Quill Gardens Boutique Hotel
Talk of the Town
Talk of the Town
3 out of 5
L.E. Saddler Road #9, Oranjestad, St. Eustatius
  • 25 min drive from Dutch Museum of Saba
The price is $111 per night from Apr 27 to Apr 28
$111
per night
Apr 27 - Apr 28
Stay at this 3-star hotel in Oranjestad. Enjoy free WiFi, free parking, and a terrace. Popular attractions Government Guesthouse and Dutch Reformed Church are ...
9/10 Wonderful! (4 reviews)
"Quiet and relaxing"

Reviewed on Mar 9, 2024

Talk of the Town
Queen’s Hotel Saba
Queen’s Hotel Saba
4 out of 5
Troy Hill #1, The Bottom, Saba
  • 9 min walk from Dutch Museum of Saba
Stay at this 4-star resort in The Bottom. Enjoy free WiFi, breakfast, and in-room massages. Popular attractions Catholic Church and Mt Scenery are located nearby. ...
5.8/10 (15 reviews)
"Service is good"

Reviewed on Nov 17, 2023

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Queen’s Hotel Saba
Barrel House St. Eustatius
Barrel House St. Eustatius
3 out of 5
Van Tonningen Weg, Oranjestad, Sint Eustatius
  • 26 min drive from Dutch Museum of Saba
Stay at this 3-star beach B&B in Oranjestad. Enjoy free WiFi, free parking, and 2 restaurants. Popular attractions Lower Town Beach and Fort Oranje are located ...
8/10 Very Good! (1 review)
"Ce n’est pas un hôtel, comme indiqué sur Expédia : pas de réception, pas de piscine, mais une simple maison. La propriétaire a « manqué notre réservation » : donc logement pas préparé à notre arrivée. Puis elle parle de vérifier si nous avons réservé la formule avec petit déjeuner, alors qu’Expedia ..."

Reviewed on Jan 5, 2024

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Barrel House St. Eustatius
Palm Spring Inn
Palm Spring Inn
3 out of 5
Erick R Gibbs Road 2, Cherry Tree, Sint Eustatius, Oranjestad
  • 26 min drive from Dutch Museum of Saba
Stay at this 3-star apartment in Oranjestad. Enjoy free WiFi, free parking, and babysitting services. Popular attractions Government Guesthouse and Dutch Reformed ...
8.4/10 Very Good! (14 reviews)
NASTY SUITE TERRIBLE SERVICE
"Arrived late, well advanced noticed sent to owner. Was met by a man at hotel who showed us suite and gave us keys and wifii password. This man told us the owner will comeby the following day. No show. Apartment was nasty as if the last guest left and we arrived. Used bag of ice in freezer, dish on ..."

Reviewed on Apr 18, 2023

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Palm Spring Inn
See all 27 properties in Windward Side
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.

HOTW-Hotel-Deals-726-959@2x.jpg (1918×258)*Savings based on Hot Rate® hotel bookings as compared with the lowest published rates found on leading retail travel sites. Hot Rates are different from retail rates. With Hot Rates you enter the date, location and star rating. Hotel revealed only after booking. All bookings final.

Find cheap hotels in Windward Side

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Windward Side hotel with Hotwire to complete your one-of-a-kind travel checklist.

For you, intrepid voyager, Hotwire has a large selection of the best hotels in Windward Side.

Choosing the right hotel in Saba has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Windward Side’s 27 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $79. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get up to 60% Windward Side hotel deals at the last minute.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Windward Side. No matter your reason for visiting Windward Side, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About Windward Side hotels

Where can I find the best last-minute travel deals?

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can save up to 60% off your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Windward Side for as low as $79.

How many hotels are there in Windward Side?

With over 27 hotels in Windward Side, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $79.

How to find cheap car rentals in Windward Side?

Finding a cheap car rental deal in Windward Side is as easy as scoring cheap hotels in Windward Side. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can even save up to 60% off a car rental deal if you book a Hotwire Hot Rate at the last minute.

Is it safe to travel to Windward Side now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Windward Side right now?” When it’s time to book your getaway, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.