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Hotels in Windward Side

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This weekend
May 22 - May 24
Next weekend
May 29 - May 31

Where to stay in Windward Side?

Outdoor pool

Saba Arawak Hotel

Saba Arawak Hotel
3.0 star property
Windward Side
8.4 out of 10, Very Good, (90 reviews)
Dive into Caribbean paradise at this Windward Side hotel with an outdoor pool and on-site restaurant serving local cuisine. Explore nearby Dutch Museum of Saba and Heritage Center, then return to comfort with free WiFi and convenient parking.
The price is $135
$159 total
includes taxes & fees
May 21 - May 22
Saba Arawak Hotel
Exterior

Golden Rock Dive And Nature Resort

Golden Rock Dive And Nature Resort
4.5 star property
Oranjestad
9.6 out of 10, Exceptional, (52 reviews)
Escape to this luxurious getaway with 2 outdoor pools just minutes from Oranjestad Airport. Enjoy massages at the spa, dine at Restaurant Breeze, or sip drinks at the poolside bar while exploring The Quill and White Wall nearby.
The price is $399
$448 total
includes taxes & fees
May 20 - May 21
Golden Rock Dive And Nature Resort
Aerial view

The Cottage Club Hotel

The Cottage Club Hotel
3.5 star property
Windward Side
10.0 out of 10, Exceptional, (1 review)
Immerse in island charm at this Windward Side haven with a refreshing outdoor pool and free WiFi. Explore Harry L Johnson Museum nearby while enjoying a tropical garden terrace. Free parking and daily housekeeping ensure a carefree Caribbean stay.
The Cottage Club Hotel
On the beach, scuba diving

The Old Gin House

The Old Gin House
3.0 star property
Oranjestad
8.4 out of 10, Very Good, (62 reviews)
Steps from Fort Oranje and Lower Town Beach in Oranjestad, this Colonial hotel offers seaside charm with an outdoor pool. Unwind at one of 2 bars or savor meals at the on-site restaurant while enjoying garden views, free breakfast, and WiFi.
The price is $190
$203 total
includes taxes & fees
May 22 - May 23
The Old Gin House
Classic Single Room, Resort View | In-room safe, free WiFi

The Scenery Hotel Saba

The Scenery Hotel Saba
2.0 star property
Windward Side
The Scenery Hotel Saba
Premium Bungalow, Non Smoking | Living area

Talk of the Town Inn & Suites

Talk of the Town Inn & Suites
3.0 star property
Oranjestad
8.6 out of 10, Excellent, (18 reviews)
This Oranjestad hotel offers island convenience with free WiFi and complimentary parking. Swim in the outdoor pool, unwind on the terrace, or stroll through the garden. Government Guesthouse and Dutch Reformed Church are just minutes away for cultural exploration.
The price is $107
$115 total
includes taxes & fees
May 27 - May 28
Talk of the Town Inn & Suites
View from property

Barrel House St. Eustatius

Barrel House St. Eustatius
3.0 star property
Oranjestad
8.0 out of 10, Very Good, (1 review)
Unwind at this coastal retreat with 2 on-site restaurants and a welcoming bar/lounge. Located near Lower Town Beach and Fort Oranje, this B&B offers free WiFi and parking, just a 2-minute drive from F.D. Roosevelt Airport.
The price is $197
$210 total
includes taxes & fees
May 28 - May 29
Barrel House St. Eustatius
Beach

Statia Lodge

Statia Lodge
3.0 star property
Oranjestad
4.8 out of 10, (5 reviews)
Experience the charm of St. Eustatius at this welcoming lodge with complimentary cooked-to-order breakfast and free parking. Just minutes from Fort de Windt and the famous White Wall, enjoy garden surroundings, a peaceful terrace, and daily housekeeping service.
The price is $150
$176 total
includes taxes & fees
May 20 - May 21
Statia Lodge
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.
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When is the best time to visit Windward Side?

Our prices for hotels in Windward Side are cheapest in November
Price trends for hotels in Windward Side
Pricing is based on two traveler single night rates
View properties in May
Currently viewing crowd sizes and weather for May.
Typical weather for Windward Side
May
High 27°C / low 26°C. Cloudy most days.
View properties in May
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May, no crowd data, average high temperature 27 degrees Celsius, average low temperature 26 degrees Celsius. Cloudy most days.
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June, no crowd data, average high temperature 28 degrees Celsius, average low temperature 27 degrees Celsius. Sunny most days.
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July, no crowd data, average high temperature 28 degrees Celsius, average low temperature 27 degrees Celsius. Sunny most days.
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August, no crowd data, average high temperature 29 degrees Celsius, average low temperature 27 degrees Celsius. Sunny most days.
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September, no crowd data, average high temperature 29 degrees Celsius, average low temperature 27 degrees Celsius. Sunny most days.
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October, no crowd data, average high temperature 29 degrees Celsius, average low temperature 27 degrees Celsius. Cloudy most days.
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November, no crowd data, average high temperature 28 degrees Celsius, average low temperature 27 degrees Celsius. Cloudy most days.
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December, no crowd data, average high temperature 27 degrees Celsius, average low temperature 26 degrees Celsius. Sunny most days.
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January, no crowd data, average high temperature 26 degrees Celsius, average low temperature 25 degrees Celsius. Sunny most days.
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February, no crowd data, average high temperature 26 degrees Celsius, average low temperature 25 degrees Celsius. Sunny most days.
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March, no crowd data, average high temperature 26 degrees Celsius, average low temperature 25 degrees Celsius. Sunny most days.
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April, no crowd data, average high temperature 26 degrees Celsius, average low temperature 25 degrees Celsius. Sunny most days.
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Monthly weather averages (˚C)

Top landmarks in Windward Side

Dutch Museum of Saba

4.2/5 (5 reviews)
The center of Windward Side is home to cultural attractions like Dutch Museum of Saba, so you might want to stop by during your stay. If you want to experience more of the culture Windward Side has to offer, head to Mt Scenery, Cove Bay Beach, and Well's Bay Beach.
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Learn more about Windward Side

Windward Side is applauded for its cultural attractions such as Dutch Museum of Saba and Harry L Johnson Museum. The city has something for everyone including sights like Mt Scenery and Jo Bean Glass Art Studio within a scenic setting.

See all hotels in Windward Side
Photo by Stills 'n' stories
Open Photo by Stills 'n' stories

Check out reviews of Windward Side hotels guests love

The Old Gin House

The Old Gin House

10/10 Excellent
"Excellent "
Christine 3-night trip
Posted 3 hours ago
The Old Gin House

Frequently asked questions

What accommodations do travelers recommend in Windward Side?
Guests like Saba Arawak Hotel, El Momo Cottages and The Cottage Club Hotel.
Where can I find free parking with my stay in Windward Side?
El Momo Cottages offers the perk of free parking.
Can I book refundable hotels in Windward Side?
If you're looking for the flexibility to change your plans to Windward Side, most properties offer refundable* bookable rates. You can see these properties by searching our site and using the "fully refundable" filter to narrow down the results.
Where can I stay in Windward Side if I'm looking for a reasonably priced accommodation?
The Scenery Hotel Saba is an accommodation you might want to consider that'll save you money.
What will the weather in Windward Side be like during my visit?
Windward Side is a great place to visit any time of year with an average temperature of 78°F during the coldest months.
Why should I book my Windward Side hotel with Hotels.com?
There are lots of reasons to book your Windward Side trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.