Photo by Meghan Watters

Search Cottages in Windward Side

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
7 Feb - 9 Feb
In two weeks
14 Feb - 16 Feb
In one month
28 Feb - 2 Mar
In two months
28 Mar - 30 Mar

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

Flamboyant Cottage - Spectacular View & Pool
Flamboyant Cottage

Flamboyant Cottage - Spectacular View & Pool

9.8 out of 10, Exceptional, (37)
"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
Peter Hytte is close to everything at great price!
Front balcony

Peter Hytte is close to everything at great price!

Peter Hytte is close to everything at great price!
Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
Althea from above it all

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!
Your very own cottage
Exterior

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.
Don't see what you're looking for?
See all available properties in Windward Side
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Windward Side

Flamboyant Cottage - Spectacular View & Pool
Flamboyant Cottage

Flamboyant Cottage - Spectacular View & Pool

9.8 out of 10, Exceptional, (37)
"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
Peter Hytte is close to everything at great price!
Front balcony

Peter Hytte is close to everything at great price!

Peter Hytte is close to everything at great price!
Spyglass is a Private Villa With 360 View Near Windwardside.
Choose your breakfast spot...

Spyglass is a Private Villa With 360 View Near Windwardside.

9.8 out of 10, Exceptional, (66)
"We loved it here so much, we already booked it for Christmas next year. nuff said. "
Spyglass is a Private Villa With 360 View Near Windwardside.
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.