Photo by Meghan Watters
Search Cottages in Windward Side
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare Cottages in Windward Side with updated reviews, rates, and availability.

Flamboyant Cottage - Spectacular View & Pool
Flamboyant Cottage - Spectacular View & Pool
9.8 out of 10, Exceptional, (40)

Peter Hytte is close to everything at great price!
Peter Hytte is close to everything at great price!
10.0 out of 10, Exceptional, (1)

Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
10.0 out of 10, Exceptional, (10)

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.
Save an average of 15% on thousands of hotels when you're signed in
Other property types in Windward Side

Flamboyant Cottage - Spectacular View & Pool
Flamboyant Cottage - Spectacular View & Pool
9.8 out of 10, Exceptional, (40)

Spyglass is a Private Villa With 360 View Near Windwardside.
Spyglass is a Private Villa With 360 View Near Windwardside.
9.8 out of 10, Exceptional, (68)

Peter Hytte is close to everything at great price!
Peter Hytte is close to everything at great price!
10.0 out of 10, Exceptional, (1)
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.
Recent reviews of Windward Side hotels
Recent reviews of Windward Side hotels

Flamboyant Cottage - Spectacular View & Pool
5/5 Excellent
Spectacular
"So lovely , whimsical, the view, the pool was so wonderful to cool off. Saba is magical.The cottage was clean and so many outdoor sitting spots.Could not recommend it more "
A verified traveler from Ontario, Canada stayed at Flamboyant Cottage - Spectacular View & Pool
Posted 3 weeks ago