Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Windward Side on Hotels.com. These Windward Side hotels consistently deliver on quality, location and traveler experience. Last updated on October 12, 2026.
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.
Rustic cottages nestled on Saba Island with an outdoor pool for cooling off after exploring. Just minutes from the Dutch Museum and Heritage Center, this tranquil retreat offers lush garden surroundings and a welcoming restaurant terrace.
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.
Unwind at this boutique guesthouse with lush garden surroundings and a refreshing outdoor pool. Just 3 minutes from Roosevelt Airport with free breakfast, WiFi and parking. Grab drinks at the bar after exploring nearby Government Guesthouse.
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.
Experience comfortable island living at this welcoming inn featuring apartments with full kitchens and private balconies or patios. Located near Government Guesthouse and Dutch Reformed Church, with free WiFi and parking for added convenience.
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.
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.
The center of Windward Side is home to cultural attractions like Saba Heritage Center, 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 Dutch Museum of Saba, Mt Scenery, and Cove Bay Beach.
The center of Windward Side is home to cultural attractions like Harry L Johnson Museum, 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 Dutch Museum of Saba, Mt Scenery, and Cove Bay Beach.
If museums are on your list of things to see, then you might want to head to Jo Bean Glass Art Studio, located in the heart of Windward Side.If you want to see more of the museums in Windward Side, you can easily walk to Dutch Museum of Saba or Saba Heritage Center.
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 Saba Heritage Center within a scenic setting.
Care to make simple cabins welcoming, such as chalk-board greeting and tropic flower. The scene, and owners, are ultra casual.
This property is not for the faint on breath, given the somewhat irregular 70+ plus steps from roadway to the pool and office. Then there are additional steps to individual cabins, challenging again in some cases.
Due to a cancellation, I was able to occupy the Turtle cabin, a bargain and must-do upgrade at only $20 additional. The unit has a generous projecting deck...
This hotel is a must visit. The hotel itself is located on the small island of Statia and sits right on the water. The staff is amazing, but the hotel bar is a historical masterpiece. The food was great and the atmosphere is world class. This hotel far exceeded my expectations and I am so very happy that I happened to come across it. If you ever find yourself in Statia, then this is the hotel that you will want to stay at. Also, this Hotel has incredible taste in music.
You can find top hotels in Windward Side from CNY690 with options to suit your budget and needs. If you're after an affordable hotel in Windward Side that meets all of your requirements, set your filters and then sort the results by "Price: low to high".
How can I find deals and earn rewards at Windward Side hotels?
Discover great deals on Windward Side hotel stays with Hotels.com. Take a look at hotel prices mid-week or during the low season as to find those off-peak deals. And make sure to check out our last-minute deals on Windward Side hotels.
Can I book Windward Side hotels with free cancellation?
In order to book a refundable Windward Side hotel, simply filter hotels by "Property cancellation options" and select "Fully refundable property". The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.
What are the top Windward Side hotels with a pool?
Discover some of the best Windward Side hotels with a pool for a little extra luxury on your trip. The Cottage Club Hotel is a great hotel with an outdoor pool and a guest rating of 10 out of 10. Plus, you can make the most of its free parking and terrace. Saba Arawak Hotel is a popular hotel that features an outdoor pool along with an ocean-view restaurant and a bar/lounge. To find more stays in Windward Side with a pool, use the "Amenities" filter on Hotels.com in your search and select "Pool".
What are some of the best Windward Side hotels with free parking?
If you're arriving by car, choosing a great Windward Side hotel with free parking is a plus. Our travelers' favorites include:
What are some popular hotels in central Windward Side?
If you're looking for hotels in central Windward Side, check out The Cottage Club Hotel and Saba Arawak Hotel. Travelers love The Cottage Club Hotel for its location, as well as the outdoor pool, free parking and terrace this hotel offers. Saba Arawak Hotel is another popular central hotel with an outdoor pool, an ocean-view restaurant and a bar/lounge.
