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Find hotels in Windward Side from £85

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Top 10 Windward Side hotels and places to stay

2023 Villa Fairview on Saba. Ultimate privacy.
Pool
2023 Villa Fairview on Saba. Ultimate privacy.
10.0 out of 10, Exceptional, (3)
"Villa Fairview was gorgeous! The views and the ambiance are unbeatable, and visitors get the full island experience: amazing sunsets, hills, cloud cover, rain, and ocean breezes. Leaving the doors open is magical, but it does come with a side of insects that serve to contribute to the experience. The pool will cool you off on a hot day, and the place has everything you could need, including a great kitchen and laundry room. I’d definitely stay here again!"
2023 Villa Fairview on Saba. Ultimate privacy.
Modern Luxury Villa in Flatlands. Pool. Walk to Beach. Sleeps 6. Ocean Views.
Pool | Outdoor pool
Modern Luxury Villa in Flatlands. Pool. Walk to Beach. Sleeps 6. Ocean Views.
10.0 out of 10, Exceptional, (4)
"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!"
Modern Luxury Villa in Flatlands. Pool. Walk to Beach. Sleeps 6. Ocean Views.
The Cottage Club Hotel
Mountain view
The Cottage Club Hotel
3.5 star property
10.0 out of 10, Exceptional, (1)
"Beautiful views. Very centrally located and quiet. "
The Cottage Club Hotel
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Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
Property grounds
Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
10.0 out of 10, Exceptional, (6)
"Very pleased with the responsiveness of the owner, and location of the property. Exactly what we were looking for. Hope to stay again."
Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
Home a way from home in the Unspoiled queen of the Caribbean.
Exterior
Home a way from home in the Unspoiled queen of the Caribbean.
10.0 out of 10, Exceptional, (2)
"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."
Home a way from home in the Unspoiled queen of the Caribbean.
Spyglass is a Private Villa With 360 View Near Windwardside.
Outdoor dining
Spyglass is a Private Villa With 360 View Near Windwardside.
10.0 out of 10, Exceptional, (61)
"Very nice villa with some of the most spectacular views you’ll find anywhere in the world. Good hikers can walk into/from the village of Windwardside — be prepared for a steep hill on return. We were 4 adults, though 6 would be very comfortable. All conveniences are in the house. Mgmt: 1 sink awaiting repair parts; we never found the orientation book. We appreciated the mid-week cleaning service, but would like to be notified of that before they intrude on our privacy."
Spyglass is a Private Villa With 360 View Near Windwardside.
Beautiful Gingerbread Cottage - Spectacular View & Pool
Exterior
Beautiful Gingerbread Cottage - Spectacular View & Pool
9.8 out of 10, Exceptional, (32)
"This place was beautiful, so peaceful and the views and pool were perfect. A well appointed kitchen and plenty of outdoor spaces to enjoy. Michael was an extremely helpful host coordinating transport easily and even making the occasional dinner reservation for us. Wonderful island, visit if you feel like completely relaxing!"
Beautiful Gingerbread Cottage - Spectacular View & Pool
Saba Arawak Hotel
View from room
Saba Arawak Hotel
3.0 star property
8.6 out of 10, Excellent, (28)
"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 nice stay and the staff and owner were very nice and helpful! "
The price is £121
per night
3 May - 4 May
Saba Arawak Hotel
El Momo Cottages
Outdoor pool, pool loungers
El Momo Cottages
3.0 star property
8.6 out of 10, Excellent, (44)
"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 did not sleep well. "
The price is £85
per night
3 May - 4 May
El Momo Cottages
Poets and Painters Cottage
Property grounds
Poets and Painters Cottage
The price is £328
per night
3 May - 4 May
Poets and Painters Cottage
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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.

Accommodation near Windward Side attractions

Image for Dutch Museum of Saba

Dutch Museum of Saba

You can spend time studying the exhibits at Dutch Museum of Saba during your travels in Windward Side. While you're in the area, wander around the gardens.

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Dutch Museum of Saba

Windward Side Travel Info

Number of hotels
28
Highest price
£328
Lowest price
£85
Known attractions
Well's Bay Beach, Cove Bay Beach and Dutch Museum of Saba
Hotels with nearby historical attractions
2
Hotels with free breakfast
2

Frequently asked questions

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 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 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.

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 16 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 and Harry L Johnson Museum. A couple of additional sights to add to your itinerary are Saba Heritage Center 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.

Windward Side Hotel Reviews
Expedia verified reviews

The Old Gin House Hotel

The Old Gin House Hotel

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 Hotel
Posted 2 weeks ago
The Old Gin House Hotel