Windward Side Hotel & Accommodation Deals 2025 from AU$163

Q: What are some hotels with pools in Windward Side?

Saba Arawak Hotel : Features complimentary high-speed (wired) Internet access, an outdoor pool and free self parking. Another option that features an on-site pool is El Momo Cottages . View all hotels with pools in Windward Side .

Top hotels and accommodation in Windward Side

"Loved everything about it. The views, the spacious room and bathroom, the pool, the food, close proximity to stores and supermarkets, right by the hiking trail, it was perfect. "

includes taxes & fees

5 Dec - 6 Dec

"I had a wonderful visit at El Momo. I was in Saba for hiking and the cottages were nestled into the woods, giving the perfect setting for enjoying the natural surroundings. The view from the cottages was amazing, the pool was a perfect spot to relax after a day out. The staff was helpful and friendly. "

includes taxes & fees

11 Dec - 12 Dec

"We absolutely loved our week at Spyglass! The home has the feel of a traditional Saba cottage, with some of the BEST views in the Caribbean. We love this small island. The hiking is amazing, the diving is world class, and we love the local food. The home is in a private location, very peaceful and quiet. We would definitely choose to stay here again. If you lead an active lifestyle and enjoy walking/hiking, you can easily walk to the main areas in the village of Windwardside where the local...

"You can't get a better spot/place in Saba. This quaint cottage has views to die for, as well as everything you need in a vacation rental. Plus it has a pool. No need for AC either since the breezes, along with the fans keep the place quite comfortable. I know some guests stated they walked to Windwardside....quite a hike. We rented a car which worked perfect. Communication with Michael the property manager, and Larry the owner was perfect. "

"The people of Saba are very friendly. This location has many fantastic restaurant choices within a short walk. Our host Jeffery was wonderful. Very helpful. Because he lives next door he's always available. The cottage was roomy for the 2 of us. WiFi worked great and there's plenty of electrical outlets (American Style 110 volt). I can say enough nice things about this rental."

"Beautiful views. Very centrally located and quiet. "

"Even though we had to pay for an unused night on account of a canceled ferry, this was a beautiful place in a gorgeous location close to everything in Windwardside. My kids and I enjoyed the private pool with a view."

"We really enjoyed our stay in this beautiful cottage. It's location is great on the Windward Side of Saba. Close to My Scenery, several shops, basically everything you need. The home was spotless and had all the amenities you could ask for. Communication was great and check in was seamless. Margarita was great. I highly recommend it. Looking forward to returning to Saba soon."

"Our stay was fantastic! Cece was awesome and helpful in every way! She arranged a rental car for us at the house so we could get around the island independently. Views were magnificent and hacienda was perfect! Very clean with every amenity you could possibly want! Kitchen is fully stocked with anything you could possibly need to cook a meal. Don’t hesitate to book this magnificent home! You won’t be sorry!"

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Windward Side Travel Info

Number of reviews	178
Accommodation	29 hotels
Highest price	AU$233
Lowest price	AU$163
Reasons to visit	Wells Bay Beach, Cove Bay Beach and Dutch Museum of Saba
Hotels with nearby hiking	5
Hotels with jungles	4

Recent Reviews in Windward Side

5/5 Excellent

"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 to another excellent restaurant, as well as a scuba center for those who come to Statia to dive. Thanks to Peter and Jeanette and your amazing staff!"

A verified traveller stayed at The Old Gin House

Posted 8 months ago

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Frequently asked questions

Where is the best place for a stay in Windward Side?

El Momo Cottages is ranked highly by Expedia customers. This guest house offers a restaurant and an outdoor pool. Another top choice for your visit based on reviews is Saba Arawak Hotel. See all available top hotels, or vacation rentals in Windward Side.

What are some of the best holiday rentals that Windward Side has to offer?

Home a way from home in the Unspoiled queen of the Caribbean.: This highly rated holiday home rental in Windward Side is located in the city centre, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a garden. Some other top choices in Windward Side are Poets and Painters Cottage and Beautiful Traditional Saba Cottage With all the Modern Amenities. See all vacation rentals in Windward Side.

If I need to cancel my hotel reservation in Windward Side, will I receive a refund?

Yes, most hotel reservations are fully refundable provided that you cancel prior to the hotel's cancellation deadline, which is usually within 24-48 hours of check in. If you have a reservation that's non-refundable, it may still be possible to cancel it and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Windward Side.

What's the best family accommodation in Windward Side?

El Momo Cottages is a guesthouse with an outdoor pool and a restaurant, and it's a top choice on Expedia for families. Find more child-friendly accommodations in Windward Side.

What's the best place to stay for a couple going to Windward Side?

El Momo Cottages is a favourite guest house for couples, and features free WiFi and a garden. See all romantic hotels in Windward Side.

What's the best dog-friendly place to stay in Windward Side?

El Momo Cottages is a top guest house for people travelling 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 place to stay for a beach holiday in Windward Side?

Scout's Place Hotel is a top hotel with free continental breakfast and free WiFi, and it's located close to Cove Bay Beach . Other good options for your beach trip include Juliana's Hotel and El Momo Cottages. See more stays near the beach in Windward Side.

What's the best boutique-style accommodation in Windward Side?

Selera Dunia Boutique Hotel is a favourite 3-star B&B with our travellers looking for stylish accommodation, and features 2 guestrooms, free breakfast and free parking.

What are some hotels with pools in Windward Side?

Saba Arawak Hotel: Features complimentary high-speed (wired) Internet access, an outdoor pool and free self parking. Another option that features an on-site pool is El Momo Cottages. View all hotels with pools in Windward Side.

How is it 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 15 hotels and other accommodation options to choose from. Find out more about Windward Side.

What should I do while I'm visiting Windward Side?

Cultural venues include Dutch Museum of Saba, Saba Heritage Center and Harry L Johnson Museum. A couple of additional sights to add to your itinerary are Jo Bean Glass Art Studio and Mt Scenery. Take a look at what more there is to see and do in Expedia's Windward Side guide.

What's the seasonal weather in Windward Side?

The hottest months are usually September and October, with an average temperature of 28°C, while the coldest months are February and March, with an average of 26°C. Average annual precipitation for Windward Side is 921 mm.

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Top hotels and accommodation in Windward Side

Saba Arawak Hotel

El Momo Cottages

Spyglass is a Private Villa With 360 View Near Windwardside.

Flamboyant Cottage - Spectacular View & Pool

Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!

The Cottage Club Hotel

Peter Hytte is close to everything at great price!

Home a way from home in the Unspoiled queen of the Caribbean.

Your very own cottage

Beautiful Traditional Saba Cottage With all the Modern Amenities

Modern Luxury Villa in Flatlands. Pool. Walk to Beach. Sleeps 6. Ocean Views.

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