Welcome to the Windwardside Guest Cottage, a charming little cottage that enjoys gorgeous views of the east end of St. John, the neighboring British Virgin Islands and Coral Bay. This home can be rented in conjunction with the Main House at Windwardside or alone as your own little piece of paradise.

We have numerous storage areas in a compact home with a a view that rivals any on the island. At Windwardside Guest Cottage you will wake up in a four poster bed to a gorgeous view of the Caribbean sea framed by palm trees. You could easily create a post card from the view of this adorable cottage. The interior has a queen-size, four-poster bed, a small seating area, a kitchenette and a breakfast bar. The furnishings are both tasteful and cheerful. Our goal in designing Windwardside Guest Cottage was to provide a romantic haven packed with amenities but at a reasonable price. We have many honeymoon guests that choose Windwardside Guest Cottage for precisely this reason. It is a budget home that won’t make you feel like you have made any compromises. But the cottage is not only for honeymoon couples – it is a quaint and lovely cottage for any visitors to the island that want an intimate experience of our beautiful island with a gorgeous view. A small gas grill is also available if you prefer to prepare your meals overlooking the sea. The covered porch has a dining area and two lounging chairs where you can enjoy the trade winds or a good book while watching the sailboats pass by. A shower garden opens onto an uncovered deck. There you can have a relaxing evening soak in the hot tub under a starry Caribbean sky. The hot tub also has a wide view of the sea and total privacy.

Windwardside is managed by on island owners. We will meet you on arrival, arrange for discounted car rentals and provide the personal attention you need to make your stay with us as pleasant and relaxing as possible. We can also arrange for a driver to meet your flight for the 50 minute ride to the Red Hook ferry dock. In short, Windwardside Guest Cottage offers a serene location, fabulous view, charming furnishings, a private hot tub, kitchenette and BBQ, plus dedicated staff that will organize your vacation from start to finish all for the price of a hotel room.

Windwardside Guest Cottage Weekly Rates

High Season

December 15 - April 15

1-2 Guests $1995

Low Season

April 16 - December 14

1-2 Guests $1540

+12.5% Hotel Tax

Bookings are Sunday to Sunday

Note: Until confirmed, rates are subject to change without notice.

Booking Contact:

Terri Hogg

calabashcottages@gmail.com EMAIL us with your desired schedule or Call Us

340-677-1089

Rental and Cancellation Policy

Please inquire about suitability for children.

No pets or smoking.

Trip Cancellation Insurance is highly recommended year-round.

Check for Availability.