Photo by Meghan Watters

Search Cottages in Windward Side

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Check prices for these dates

Next weekend
21 Rab. I - 23 Rab. I
In two weeks
28 Rab. I - 30 Rab. I
In one month
11 Rab. II - 13 Rab. II
In two months
9 Jum. I - 11 Jum. I

Compare 4 Cottages in Windward Side with updated reviews, rates, and availability.

Flamboyant Cottage - Spectacular View & Pool
Exterior

Flamboyant Cottage - Spectacular View & Pool

9.8 out of 10, Exceptional, (38)
"Our stay was perfect from the minute we landed on the island. Easy communication with property manager, taxi prearranged and the cottage had everything we needed! Great views, walking distance to town, restaurants and hiking. Everyone we met was SUPER friendly which made our stay extra special! "
Flamboyant Cottage - Spectacular View & Pool
Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
Aerial view

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

10.0 out of 10, Exceptional, (10)
"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."
Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
Peter Hytte is close to everything at great price!
Aerial view

Peter Hytte is close to everything at great price!

10.0 out of 10, Exceptional, (1)
"Cozy well equipt cottage. From hiking sticks to water filter and from coffee to insect repellent (not used). Etcetera.You name it."
Peter Hytte is close to everything at great price!
Your very own cottage
Terrace/patio

Your very own cottage

Your very own cottage
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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Other property types in Windward Side

Flamboyant Cottage - Spectacular View & Pool
Exterior

Flamboyant Cottage - Spectacular View & Pool

9.8 out of 10, Exceptional, (38)
"Our stay was perfect from the minute we landed on the island. Easy communication with property manager, taxi prearranged and the cottage had everything we needed! Great views, walking distance to town, restaurants and hiking. Everyone we met was SUPER friendly which made our stay extra special! "
Flamboyant Cottage - Spectacular View & Pool
Spyglass is a Private Villa With 360 View Near Windwardside.
Outdoor dining

Spyglass is a Private Villa With 360 View Near Windwardside.

9.8 out of 10, Exceptional, (68)
"The villa is even more beautiful than the pictures. The views and gardens are even more vibrant and incredible than we expected. We were amazed at the incredible construction and attention to detail in the house. The building itself looks like much of the wood work and interior is custom built and individually crafted. All appliances and appointments are top notch. The atmosphere is so peaceful. Overall the villa is airy, spacious, bright and with views into the infinity of the Caribbean. "
Spyglass is a Private Villa With 360 View Near Windwardside.
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, (3)
"Excellent place to stay for a family with kids. The pool was perfect for the kids to use up some energy. And cool off after a hike or walking the hills. The beautiful breeze that enters the main bedroom is amazing and little need for the ac to be on. Will definitely recommend to others."
Home a way from home in the Unspoiled queen of the Caribbean.
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.