Book Cheap Hotels in Windward Side
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Most frequently booked Windward Side hotels

Saba Arawak Hotel
The peak Windward Side Saba
0.17 km from city centre
The price is CA $184 per night
CA $184
CA $217 total
Apr 26 - Apr 27
includes taxes & fees
Book a stay at this business-friendly hotel in Windward Side. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Dutch Museum of Saba and Saba Heritage Center are located nearby.
Pool
Parking included

El Momo Cottages
Booby Hill Windward Side Saba
0.53 km from city centre
The price is CA $143 per night
CA $143
CA $154 total
Apr 22 - Apr 23
includes taxes & fees
Stay at this guesthouse in Windward Side. Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Dutch Museum of Saba and Saba Heritage Center are located nearby.
Pool
Pet-friendly

Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
Windward Side Saba
0.17 km from city centre
Stay at this cottage in Windward Side. Enjoy free WiFi, a garden, and patios. Popular attractions Harry L Johnson Museum and Jo Bean Glass Art Studio are located nearby.
Kitchen
Free WiFi

Flamboyant Cottage - Spectacular View & Pool
Windward Side Saba
0.76 km from city centre
Stay at this cottage in Windward Side. Enjoy free WiFi, private pools, and a garden. Popular attractions Dutch Museum of Saba and Saba Heritage Center are located nearby.
Pool
Kitchen

Spyglass is a Private Villa With 360 View Near Windwardside.
windwardside Saba
0.08 km from city centre
Stay at this villa in Windward Side. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Saba Heritage Center and Dutch Museum of Saba are located nearby.
Hot tub
Kitchen

The Cottage Club Hotel
17a Grey Bush Street Windward Side Saba
0.07 km from city centre
Stay at this hotel in Windward Side. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Harry L Johnson Museum and Jo Bean Glass Art Studio are located nearby.
Pool
Parking included

Peter Hytte is close to everything at great price!
Windward Side Saba
0.16 km from city centre
Stay at this cottage in Windward Side. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Harry L Johnson Museum and Jo Bean Glass Art Studio are located nearby.
Kitchen
Pet-friendly

The Scenery Hotel Saba
9 Fort Street Windward Side Saba
0.06 km from city centre
Stay at this hotel in Windward Side. Enjoy free WiFi, free parking, and onsite spa services. Popular attractions Saba Heritage Center and Harry L Johnson Museum are located nearby.
Spa
Parking included
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.
Windward Side hotels essential information
Accommodation | 27 hotels |
|---|---|
Lowest Price | CA $154 |
Highest Price | CA $217 |
Popular hotels | Saba Arawak Hotel, El Momo Cottages, Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!, Flamboyant Cottage - Spectacular View & Pool, Spyglass is a Private Villa With 360 View Near Windwardside., The Cottage Club Hotel, Peter Hytte is close to everything at great price!, The Scenery Hotel Saba, Home a way from home in the Unspoiled queen of the Caribbean. |
Frequently asked questions
Recent Windward Side hotel reviews by fellow wanderers

Spyglass is a Private Villa With 360 View Near Windwardside.
5 out of 5
Posted 2 days ago
Travelocity Verified Review
"We stayed at Spyglass Villa on the island of Saba from April 15–18, 2026, and it was truly an unforgettable experience. Without question, the 180-degree views are the best on the island—absolutely breathtaking from every angle.Our group of six family members had more than enough space, and the beds were incredibly comfortable. The bedding was exceptional—honestly better than what you find in many five-star hotels. We slept with the windows open each night, enjoying the cool island breezes, and had some of the best rest we’ve had in a long time.The kitchen is spacious and thoughtfully equipped, making it perfect for multiple people cooking together. Every utensil we needed was there—nothing was lacking. The bathrooms are beautifully updated, clean, and well-designed.The grounds are just as impressive as the home itself. We loved wandering around and taking in the scenery… and the views—truly incredible. The provided binoculars were a nice touch for birdwatching, and there were plenty of games available for evenings in. We especially enjoyed playing Telestrations—lots of laughs.WiFi was strong and reliable throughout our stay, which was helpful. Transportation was easy as well—our cab driver, Coochie, was always available when we needed him.One of the standout aspects of our stay was the host’s kindness and flexibility. They graciously allowed us a late checkout to accommodate our diving schedule, which made a big difference.Our favorite VRBO so far! "
A verified traveller stayed at Spyglass is a Private Villa With 360 View Near Windwardside.







