Windward Side Cottage Rentals & Holiday Homes

Frequently Asked Questions About Windward Side Rental Cottages

What are the top rated Cottage Rentals in Windward Side?

There are a lot of options in Windward Side. If you plan on staying in the Windward Side area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Windward Side:

• Modern Luxury Private Villa w Pool and Ocean Views. Walk to Beach. Sleeps 6.
• Statia's best views, comfort, privacy, & nature on a world-class diving island!
• Quill Gardens Boutique Hotel
• Barrel House Suite St Eustatius
• Golden Rock Dive and Nature Resort
• Talk of the Town Inn & Suites
• Cattleya Flor Hotel
• A Quiet Getaway
• The Old Gin House
• Talk of the Town Inn & Suites - St Eustatius

How much does it cost to rent a cottage in Windward Side?

The average cost for a cottage rental in Windward Side is $167 per night. Vacation Cottage has a wide list of great cottages near Windward Side that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Windward Side that allow pets?

Yes, here are the top cottage rentals in Windward Side that allow you to bring your pet:

• Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
• El Momo Cottages
• Beautiful Gingerbread Cottage - Spectacular View & Pool
• Your very own cottage
• Modern Luxury Private Villa w Pool and Ocean Views. Walk to Beach. Sleeps 6.
• Barrel House Suite St Eustatius
• Talk of the Town Inn & Suites
• Statia's best views, comfort, privacy, & nature on a world-class diving island!

See all pet-friendly vacation rentals in Windward Side on Vacation Cottage

Do you have any rental cottages in Windward Side that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Windward Side to find one that works for you.

Are there quality cottages in Windward Side that have indoor swimming pools?

As of 2026, the data from Vacation Cottage shows that there are Over 5 private swimming pools or cottages with indoor pools in the Windward Side area along with other great amenities.

Do any cottages in Windward Side have hot tubs?

About 5 cottages in Windward Side boast of premium hot tubs. Some of the popular places to stay with hot tubs include:

• Windward Side rentals with hot tub

Are there luxury cottages in Windward Side?

Yes, there are luxury cottages in Windward Side. Find more luxury, lakefront, winter, & last-minute cottage rentals near Windward Side.