front of the cottage - Windwardside Guest Cottage - St. John
bed and kitchen - Windwardside Guest Cottage - St. John
kitchen - Windwardside Guest Cottage - St. John
bed and seating area - Windwardside Guest Cottage - St. John
view - Windwardside Guest Cottage - St. John
porch - Windwardside Guest Cottage - St. John
hot tub and view - Windwardside Guest Cottage - St. John
seating - Windwardside Guest Cottage - St. John
kitchen - Windwardside Guest Cottage - St. John
walkway to the cottage - Windwardside Guest Cottage - St. John
outdoor shower - Windwardside Guest Cottage - St. John
Windwardside Guest Cottage - St. John
Windwardside Guest Cottage - St. John
A charming little cottage that enjoys gorgeous views of the east end of St. John
Hosted by Calabash


This home can be rented in conjunction with the main house at Windwardside or alone as your own little piece of paradise. The lush tropical plantings, built in privacy screening and the orientation of the buildings seclude them from one another. The guest cottage is very appealingly furnished, has a private hot tub, an airy enclosed shower garden and a comfortable front porch overlooking the sea.
Our goal in constructing 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.
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. 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 small gas grill is also available if you prefer to prepare your meals overlooking the sea. 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.


Iron & Board
Hair Dryer
Linens Provided
Towels Provided
Hot Tub
Charcoal Grill
High Speed Internet

Nearby activities

Scuba diving or snorkeling


No events allowed
No smoking allowed
Parking Included


These directions are for planning purposes only. You may find that construction projects, traffic, weather, or other events may cause conditions to differ from the map results, and you should plan your route accordingly. You must obey all signs or notices regarding your route.
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1 guest
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Member since: January 2018
Speaks: English

Policies and Rules

Check In: 4PM - Flexible
For first time visitors to the islands or if “it’s been a while” we prefer to meet you at the dock on St. John. We will then take you to pick up your rental car and stop for groceries before showing you out to the house. If you feel quite familiar with the island we can also arrange to meet you in Coral Bay. Whoever shows you into the house will give you a basic orientation and also go over the map. They will discuss your interests and make suggestions to help you enjoy your stay on the island as much as possible. They will point out some of the best beaches, snorkel spots, hiking trails, restaurants and shops. Feel free to ask them any questions that will enhance your stay. Our greeters are all enthusiastic residents of the island that are hoping to make your vacation as much fun as possible.
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Check Out: 10AM
No pets

Windwardside Guest Cottage - St. John is a Cottage located in St. John, U.S. Virgin Islands. This Cottage is available for short term lodging and accommodates 2 guests
Windwardside Guest Cottage - St. John has 1 bedroom, 1 bathroom and was listed on Houfy on Jan 2018

Listing # 2046 - 67 Views