A calm sea with a mountain in the distance.

Find hotels in Windward Side from ļæ„18,863

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Aug 7 - Aug 9
Next weekend
Aug 14 - Aug 16

Filter by

Property class

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Our top choices for Windward Side hotels

Outdoor pool

1. Saba Arawak Hotel

Saba Arawak Hotel
3.0 star property
Windward Side
8.4 out of 10, Very Good, (96 reviews)
"Great place to stay in Saba. Within walking distance to all the important points in the city."
United States
Jose
The price is ļæ„21,249
ļæ„24,989 total
includes taxes & fees
Aug 5 - Aug 6
Saba Arawak Hotel
Outdoor pool, pool umbrellas, sun loungers

2. Scenery Hotel Saba

Scenery Hotel Saba
3.5 star property
Windward Side
The price is ļæ„43,528
ļæ„50,365 total
includes taxes & fees
Aug 14 - Aug 15
Scenery Hotel Saba
Premium Bungalow, Non Smoking | Living area

3. Talk of the Town Inn & Suites

Talk of the Town Inn & Suites
3.0 star property
Oranjestad
8.2 out of 10, Very Good, (20 reviews)
"This is a nice place to stay when visiting Statia. They have good electric bikes (not for free), which is the best way to get around the island and know every corner of it."
United States
JosƩ Miguel
The price is ļæ„17,629
ļæ„18,863 total
includes taxes & fees
Aug 19 - Aug 20
Talk of the Town Inn & Suites
On the beach, scuba diving

4. The Old Gin House

The Old Gin House
3.0 star property
Oranjestad
8.4 out of 10, Very Good, (63 reviews)
"Very awesome hotel, great history and staff was excellent, great job."
United States
Michael
The price is ļæ„28,225
ļæ„30,327 total
includes taxes & fees
Sep 3 - Sep 4
The Old Gin House
Exterior

5. Quill Gardens Boutique Hotel

Quill Gardens Boutique Hotel
4.0 star property
Oranjestad
9.6 out of 10, Exceptional, (30 reviews)
"Great space and wonderful staff "
United States
Jennifer
The price is ļæ„29,046
ļæ„31,121 total
includes taxes & fees
Sep 3 - Sep 4
Quill Gardens Boutique Hotel
View from property

6. Barrel House St. Eustatius

Barrel House St. Eustatius
3.0 star property
Oranjestad
8.0 out of 10, Very Good, (1 review)
"Ce nā€™est pas un hĆ“tel, comme indiquĆ© sur ExpĆ©dia : pas de rĆ©ception, pas de piscine, mais une simple maison. La propriĆ©taire a Ā« manquĆ© notre rĆ©servationĀ Ā» : donc logement pas prĆ©parĆ© Ć  notre arrivĆ©e. Puis elle parle de vĆ©rifier si nous avons rĆ©servĆ© la formule avec petit dĆ©jeuner, alors quā€™Expedia affiche que le petit dĆ©jeuner est comprisā€¦ A noter aussi que la terrasse devant la maison ( cĆ“tĆ© mer) est celle du restaurant voisin."
France
ValƩrie
The price is ļæ„35,445
ļæ„38,043 total
includes taxes & fees
Aug 10 - Aug 11
Barrel House St. Eustatius
Front of property

7. Palm Spring Inn

Palm Spring Inn
3.0 star property
Oranjestad
8.4 out of 10, Very Good, (15 reviews)
"Really convenient for the airport ... But slightly further from town than expect.. Some upgrading work happening so roof top barbeque area not accessible and some noise . However room clean and large kitchen area if needed. Everyone really helpful. "
United Kingdom
lucy
The price is ļæ„22,626
ļæ„25,114 total
includes taxes & fees
Sep 2 - Sep 3
Palm Spring Inn
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Stay near popular Windward Side attractions

Saba Heritage Center

You can spend an afternoon studying the exhibits at Saba Heritage Center in Windward Side. Wander the seaside and rainforest while you're in the area.
See properties

Learn more about Windward Side

Colorful cottages with red roofs dot this charming village where hikers begin their ascent of Mount Scenery. Grab a meal at Scout's Place after exploring the Saba Conservation Foundation's trail network that winds through cloud forests.

See all hotels in Windward Side
A mountainous landscape with a body of water in the foreground.
Photo by Stills 'n' stories
Open Photo by Stills 'n' stories

Top Windward Side Hotel Reviews

Quill Gardens Boutique Hotel

Quill Gardens Boutique Hotel

10/10 Excellent
"Great stay. Everything was superb."
Donald 4-night trip
Posted 3 weeks ago
Quill Gardens Boutique Hotel

More cheap stays in Windward Side

Whale Tails Hotel

Whale Tails Hotel

the Road to Knippenga Oranjestad
Get rates

Frequently asked questions

Where is the best place for a stay in Windward Side?
Based on our traveler data, Saba Arawak Hotel is one of the top choices for your stay. This hotel offers a restaurant and an outdoor pool. Other good options for your trip include El Momo Cottages and The Cottage Club Hotel. See all available top hotels, or vacation rentals in Windward Side.
What are some of the best vacation rentals in Windward Side?
Beautiful Traditional Saba Cottage With all the Modern Amenities: Visitors give good reviews to this Windward Side vacation home rental, which is located in the mountains and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities like a stovetop and a microwave can make your vacation run smoothly. Another good choice for your trip to Windward Side is Home a way from home in the Unspoiled queen of the Caribbean.. See all vacation rentals in Windward Side.
If I need to cancel my hotel reservation in Windward Side, will I receive a refund?
Yes, you'll find most hotel bookings are refundable if you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If your reservation is non-refundable, it might still be possible to cancel it and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Windward Side.
Where can I learn more about changing or cancelling my trip to Windward Side?
For more information about rescheduling or cancelling your trip to Windward Side, go to https://www.expedia.com/service/.
What's the best pet-friendly place to stay in Windward Side?
El Momo Cottages is a top guesthouse for people traveling with their pets, and offers a restaurant and free WiFi for its human guests. See more pet-friendly hotel accommodations in Windward Side.
What's the best hotel to stay near Dutch Museum of Saba?
Adjacent to Dutch Museum of Saba, Selera Dunia Boutique Hotel is one of the top choices for your stay based on our traveler data, and this 3-star B&B offers free breakfast and free parking. Other good options close by include El Momo Cottages and The Cottage Club Hotel.
What are some hotels with pools in Windward Side?
Saba Arawak Hotel: Features complimentary wired internet access, an outdoor pool, and free self parking. El Momo Cottages and Flamboyant Cottage - Spectacular View & Pool are a couple of other choices with an onsite pool. View all hotels with pools in Windward Side.
What is the best spa hotel in Windward Side?
The Scenery Hotel Saba is a top spa hotel with 30 rooms, free WiFi, and laundry facilities. Treat yourself to a massage at the on-site spa. See all spa hotels in Windward Side.
What's the best place to stay near Juancho E. Yrausquin Airport (SAB)?
El Momo Cottages is a popular guesthouse, featuring a restaurant and an outdoor pool. It's located a short 1.4 mi (2.2 km) from Juancho E. Yrausquin Airport. Other options close to the airport are Selera Dunia Boutique Hotel and Scout's Place Hotel.
What's it like to stay in Windward Side?
Visitors can enjoy all that Windward Side has to offer including the seaside and mountain views. This city also attracts tourists with its scenic landscape. In Windward Side, there are 12 hotels and other accommodations to choose from. Find out more about Windward Side.
What should I see while I'm in Windward Side?
Cultural venues include Saba Heritage Center, Dutch Museum of Saba, and Harry L Johnson Museum. A couple of additional sights to add to your agenda are Mt Scenery and Jo Bean Glass Art Studio. Check out what more to see and do in Expedia's Windward Side guide.
What's the seasonal weather like in Windward Side?
The hottest months are usually September and October with an average temp of 83Ā°F, while the coldest months are February and March with an average of 78Ā°F. Average annual precipitation for Windward Side is 36 inches.