Cottage in St. John
2 guests · 1 bedroom · 1 bath
Reasons to book
Guests love it hereGuests give this property a top rating
Well priced for this locationPriced under area average
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About this cottage rental
Windwardside Guest Cottage is the smallest of the Calabash Cottages group but our guests love it. 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.
IMPORTANT INFO ABOUT RATES AND POLICIES: Our rental week runs from Sunday to Sunday. We have two rates: Low season from April 16 to December 14 and High season from December 15 to April 15. The rates are as listed. The only additional charge is 12.5% hotel tax. We do not collect a damage deposit. Our 20 year relationship with guests has taught us that this is not necessary. We treat our guests with respect and we have found that they return the favor. There are no extra costs for reservations, cleaning or service. If you encounter any additional charges when requesting a detailed quote it would be from the advertising site where you found us. Calabash Cottages is an established company and information about our rentals is easily found..
Car Rentals: Since the purchase of Homeaway and VRBO by Expedia we have seen an attachment at the bottom of our ads with them encouraging guests to book car rentals through their site. Because of our unique location we strongly advise against that. You do need a 4 wheel drive vehicle. We have for over 20 years done business with a very reliable company, Courtesy Car Rental. We believe in them enough that we forgo the commission they would give us and to apply it as a discount to your car rental. Please discuss car rentals with us before reserving. Our most important interest is in satisfying our customers. But the recent take over of our advertising sites by large corporations is constructing communication barriers. We can always be contacted directly.
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 good book while watching the sailboats pass by. A small gas grill is also available if you prefer to prepare your meals over looking 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.
In short Windwardside Guest Cottage offers a serene location, fabulous view, charming furnishings, a private hot tub, kitchenette and bbq, plus the dedicated staff of Calabash Cottages who will organize your vacation from start to finish all for the price of a hotel room. We provide snorkel gear, beach chairs and a cooler and a beach umbrella
We also include amenities that you may never need on our casual island (including an iron, a blow dryer and reef safe sunscreen) because we want you to be able to travel as light and carefree as possible. Please read reviews from out former guests. We hope to host you on our next visit to St. John.
IMPORTANT INFO ABOUT RATES AND POLICIES: Our rental week runs from Sunday to Sunday. We have two rates: Low season from April 16 to December 14 and High season from December 15 to April 15. The rates are as listed. The only additional charge is 12.5% hotel tax. We do not collect a damage deposit. Our 20 year relationship with guests has taught us that this is not necessary. We treat our guests with respect and we have found that they return the favor. There are no extra costs for reservations, cleaning or service. If you encounter any additional charges when requesting a detailed quote it would be from the advertising site where you found us. Calabash Cottages is an established company and information about our rentals is easily found..
Car Rentals: Since the purchase of Homeaway and VRBO by Expedia we have seen an attachment at the bottom of our ads with them encouraging guests to book car rentals through their site. Because of our unique location we strongly advise against that. You do need a 4 wheel drive vehicle. We have for over 20 years done business with a very reliable company, Courtesy Car Rental. We believe in them enough that we forgo the commission they would give us and to apply it as a discount to your car rental. Please discuss car rentals with us before reserving. Our most important interest is in satisfying our customers. But the recent take over of our advertising sites by large corporations is constructing communication barriers. We can always be contacted directly.
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 good book while watching the sailboats pass by. A small gas grill is also available if you prefer to prepare your meals over looking 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.
In short Windwardside Guest Cottage offers a serene location, fabulous view, charming furnishings, a private hot tub, kitchenette and bbq, plus the dedicated staff of Calabash Cottages who will organize your vacation from start to finish all for the price of a hotel room. We provide snorkel gear, beach chairs and a cooler and a beach umbrella
We also include amenities that you may never need on our casual island (including an iron, a blow dryer and reef safe sunscreen) because we want you to be able to travel as light and carefree as possible. Please read reviews from out former guests. We hope to host you on our next visit to St. John.
Map of St. John
Ratings and reviews
Summary of reviewsGuests praise Calabash Cottage for its magical and romantic isolated experience, surrounded by nature with helpful staff and great advice. The view, adventures, and local community create an unforgettable stay.
10 / 10Outstanding·May 2017
Calabash Cottage provides a total immersion in to St John, and it is magical. Perched high on the hill overlooking Coral bay and the lights of Tortola BVI you are surrounded by nature. This is not resort living, but, if that is what you want you probably won't get to know St John. If, however, you want a romantic, isolated experience that is comfortable as well as adventurous you cannot go wrong here. Yes you will need a Jeep, but, you will need a Jeep to explore St John so take advantage of Susan's relationship with Courtesy Rental. Susan's team will help you along the way to make everything easy. Sandra met us at the Ferry in Cruz Bay, helped us with the rental car and then led us on a tour of ST John on the way to Calabash. She was wonderful. St John is so small and intimate that we kept seeing Sandra through out our stay and getting advise from her each time. Coral Bay is a small sailing, water oriented community and everyone we met was friendly and helpful. The restaurants in Coral bay are all Good! For a fun experience visit Miss Lucy's on the way to Salt Pond and by the way go to Salt Pond and gather your own Salt. Great fun. Finally for a truly great experience buy a fish from the fisherman on the side of the road in Coral Bay (yellow tail snapper was our favorite), A bottle of wine from Love City and grill you fish on the Barbie at the cottage. If you go you will never forget your experience. Thank You Susan for sharing you island retreat.
10 / 10Outstanding·Mar 2017
The house is beautiful and wonderfully furnished. We especially loved the wildlife, the incredible amount of privacy (outside showers were the norm), and the hot tub while watching the stars. The owner's management (and owner) were professional and offered great advice. Driving the road was uncomfortable at the beginning (need 4wd), but when I remembered that the road was a big reason we had so much privacy, I was okay with the trip. We stayed at the home more than we did when we had a townhouse in Cruz Bay seven years ago because this wasn't just a place to sleep. Make sure to grocery shop in Cruz Bay before arriving; the full freezer and fridge can handle it. Full grill available. Almost no bugs when we stayed in late Feb. and early March. This side of the island is less crowded, has less crowded beaches, interesting hikes, more wildlife, and a few decent places to eat. Get to BBB for breakfast! Overall, this was a dream vacation, and I was glad I wasn't stuck in a resort sharing walls with anyone. I don't know how the house is like if someone is in the small cottage that is on the same property - seems like there would be less privacy, but I don't know. It's a very cute cottage - more of a place to sleep. Perhaps the house for the parents and the cottage for a private place for a friend/child? Overall, we won't ever forget this experience.
10 / 10Outstanding·Apr 2016
For the first time ever, my husband and I decided to vacation in the same place 2 years in a row:Windward Side Cottage in St John. We had such a fairytale perfect time there last year, we knew any other place would probably disappoint in comparison. And Windward Side cottage was every bit as clean, romantic, well-appointed, fun, and comfortable as last year. Susan and her staff think of everything and see to every detail. To wake every morning and see the sunrise and gorgeous view right from your bed, to spend the day face-down in the beautiful calm clear waters of Salt Pond Bay and other great snorkeling beaches around Coral Bay, to spend time chatting with total strangers on this friendly island, to be surprised by baby donkeys and goats around every twisty turn of the road, and to get to love the hair-raising drive up the mountain...all make us miss this beautiful place.
6 / 10Average·Jan 2017
Despite the picturesque setting, this villa was a romance killer in the heat of early June. There were no trade winds, just sticky, still heat. Just a little bit of air conditioning could have changed everything.
It was a very long ride from the airport with many winding roads. The villa is just as small as it looks and the kitchen is too small to cook in and there is only a dorm fridge and stovetop, no oven. Also no washer/dryer. In the bathroom, there was only antibacterial soap, no shower gel, shampoo or conditioner. I would not consider this villa well appointed as it is missing quite a few comforts of home.
There was a power outage which killed the only source of breeze, the fan and also no water.
My husband and I spent each day getting out as early as we could and taking in the many beautiful beaches the island offered. We stayed out as long as we could because we did not want to go back to the hot villa. It was hard to sleep, we were hot and sticky and this did not make for a very romantic setting.
Many of the beaches offer no amenities whatsoever, you must pack an ice chest with food and drinks and bring chairs (which were provided with villa). If a relaxing vacation with food and drinks on the beach is what you have in mind, this really is not the place to go. I realize that the trade-off for having no development on the beaches is the natural scenery, but we went to Grand Cayman later in the summer with our family and that is the kind of island vacation we like...air conditioners, full kitchens in the condo which is on the beach footsteps away from the water and cold drinks abound.
We ended up leaving a day early because that was the soonest we could get out with making a flight change. We have no interest in going back to St. John.
The owner did offer us use of the larger home nextdoor with a full kitchen, etc. but we did not find it to be any cooler over there. She also was able to give us a partial refund for the unused time of the rental car, but nothing on the villa.
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Top rated by guests
9.8Outstanding
(31 Ratings)
Guests praise Calabash Cottage for its magical and romantic isolated experience, surrounded by nature with helpful staff and great advice. The view, adventures, and local community create an unforgettable stay.
From real guest reviews summarized by AIDon't miss out! Price and availability may change
