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Windwardside Cottage: Quaint, Quiet, romantic, Spa, Great Ocean View & gardens

Bedrooms 1
Property type cottage
Minimum Stay 1 - 7 nights


About the property

1BR Oceanview Vacation Rental St. John, Virgin Islands USA

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 and a blow dryer) 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.

More Details

Property Manager
Susan Brierley
Member since: 1998
Speaks English
Response time:
Within 12 hours
Response rate:
Calendar last updated:
22 June, 2018

About Susan Brierley

We are thirty year residents of St. John. My husband is a retired builder and we designed this home together. We built Windwardside in 1996 and have managed it as part of the Calabash Cottages group for over 20 years. Calabash Cottages offers charming and private cottages and villas in quiet secluded locations. Our main focus is to provide an assortment of options for couples in a tranquil setting.

We and our staff always do our best to insure your precious vacation time is well spent at one of our Calabash Cottages. We are very happy to answer any questions to help you decide if Windwardside Guest Cottage or one of our other Calabash Cottages is a good fit for you.

Susan Brierley purchased this cottage in 1996

Why Susan Brierley chose Estate Calabash Boom

We love Coral Bay and wanted to design a home that did not tower over the hillside but fit into it's natural surroundings. The shape and orientation allowed of this property allowed us to do just that while still offering fabulous views. We love quiet natural settings, tropical gardens and ocean views and we appeal to visitors who are looking for just that.

What makes this cottage unique

Windwardside Guest Cottage will make you fall in love with the view from the front porch. The first thing you will see in the morning right from your four poster bed is the palm fronds waving in the breeze. This compact cottage offers many amenities. It is also a great choice for two couples when rented with Windwardside Main House as each has a lot of privacy.


Accommodation and facilities for this holiday cottage in Estate Calabash Boom in Coral Bay

Property Type:
  • cottage
  • Self-catering
House Rules:
  • Max. occupancy: 2
  • not suitable for children
  • pets not allowed
Location Type:
  • Beach View
  • mountain
  • Mountain View
  • near the sea
  • Ocean View ...
  • village
  • Water View
  • Adventure
  • Away From It All
  • Romantic
  • Alarm Clock
  • Basic Soaps
  • Ceiling Fans
  • Filtered Water
  • Free Local Calls
  • Hair Dryer
  • Internet
  • Iron & Board
  • Linens Provided ...
  • Local Activities Guide
  • Local Maps
  • Local Restaurant Guide
  • Paper Towels
  • Parking
  • Parking Off Street
  • Safe
  • Telephone
  • Toilet Paper
  • Towels Provided
  • Wireless Internet
  • Blender
  • Coffee Grinder
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Kitchen ...
  • Kitchenette
  • Mini Refrigerator
  • Refrigerator
  • Hob
  • Stove
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 2 people
  • 1 Bathroom
  • Bathroom - Toilet , Shower Enclosure , Outdoor Shower , Toilet, sink and vanity indoors. Outdoor shower.
  • Spacious enclosed outdoor shower with shower garden
  • 1 Bedroom, Sleeps 2
  • Bedroom - 1 Large Double Bed
  • Books
  • CD Player
  • DVD Player
  • Radio
  • Stereo
  • Television ...
  • Video Library
  • Balcony
  • Deck Chairs
  • Beach Towels
  • Beach Umbrellas
  • Terrace ...
  • Deck Furniture
  • Large Cooler
  • Garden
  • Barbecue
  • Outdoor Grill Gas
  • Porch Furniture
  • Small Cooler
  • veranda
  • Water Sports Gear ...
  • Wood Decking
  • 2 deck chairs
  • wheelchair inaccessible
Pool / Spa:
  • Hot Tub ...
  • Outdoor Hot Tub
  • churches
  • duty free shops
  • forests
  • Health/Beauty Spa
  • library
  • reefs
  • restaurants
  • ruins
Leisure Activities:
  • beachcombing
  • bird watching
  • Boating
  • eco tourism
  • horse riding
  • Shopping
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • fitness centre
  • groceries
  • laundrette - serviced
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • deepsea fishing
  • fly fishing
  • hiking
  • Kayaking
  • Parasailing
  • sailing
  • diving
  • snorkelling
  • Snorkeling/Diving
  • bay fishing
  • swimming
  • tennis
  • wind-surfing


Wonderful! 4.9/5 -
(31 traveller reviews)

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Windwardside Cottage: Quaint, Quiet, romantic, Spa, Great Ocean View & gardens
average rating of 4.903226 based on 31 reviews

Magical Location on a magical island

  • 5 of 5

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.

  • Review Submitted: 27-May-2017
  • Date of Stay: May 2017
  • Source: VRBO, from HomeAway
Owner's Response: I really appreciate your review of Windwardside and it's always fun to hear how our guests spent their vacations. Thanks for writing and for spending your vacation with us. Hope to see you again! Susan
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Privacy, wonderful like kings

  • 5 of 5

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.

  • Review Submitted: 06-Mar-2017
  • Date of Stay: February 2017
  • Source: VRBO, from HomeAway
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New Orleans, LA

Hot, uncomfortable honeymoon, left early.

  • 3 of 5

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.

  • Review Submitted: 15-Jan-2017
  • Date of Stay: June 2016
  • Source: VRBO, from HomeAway
Owner's Response: My staff and I are known for going the extra mile to make sure our guests are happy. Our interactions with this guest were no exception. First, we try to make sure they are a good fit for our property since the location is remote. We also tell our guests (especially those from hotter states) that we have only fans (a fan over the bed and a tower fan on each side of it). As these guests were coming from Louisiana we most certainly had this discussion. When the guests indicated that they were uncomfortable, I offered them a much more expensive house that had more amenities but they declined. When they decided to leave and thus return their car early, it was beyond the cancellation period so I paid for it myself. I don't know what else I could have done. Lastly, St. John is great for folks looking for a tranquil and unspoiled island, picture postcard beaches, fun local music and charming cottages. This did not seem to be what these guests were looking for. If they were unhappy with their stay on the island and in our cottage, we feel it was due to a difference in expectation
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Caribbean Dream Cottage

  • 5 of 5

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.

  • Review Submitted: 15-Apr-2016
  • Date of Stay: April 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thank you for such a lovely review of Windwardside Guest Cottage and your time on the island. We do our best to anticipate guests needs but it is always nice to hear that we have succeeded. Vacation time is precious I am so happy to hear that you enjoyed yours. Hope to see you again! Susan
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Wonderful Vacation!!

  • 5 of 5

Our experience with the Calabash Cottage staff could not have been better, they took care of every detail! We had a wonderful trip and plan to return some day soon. We will most definitely do business with this rental company again. Thanks for everything!

  • Review Submitted: 29-Feb-2016
  • Date of Stay: December 2015
  • Source: VRBO, from HomeAway
Owner's Response: Hi Roberta, We really appreciate your lovely review. I'm so glad that the cottage met your expectations and that you found the staff so helpful. I am very lucky to have them! Hope to see you on another visit. Susan
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Great honeymoon stay!

  • 5 of 5

Perfect place for a 2 person getaway! All the staff made planning and everything on travel days go really smooth and stress free--arranging taxis, rental cars, and generally having good advice. The house itself was great, very small but has everything you need. The views from the cottage are amazing. The hot tub was great, we used it every night! The drive up from the main road to the cottage is pretty intimidating, but went well after the first time. Close to quite a few good restaurants on that side of the island. If you cook, make sure to clean the dishes right away and get up any crumbs, as the ants will find their way in quickly (but if you clean well won't be a problem). Also loved the outdoor shower!

  • Review Submitted: 28-Dec-2015
  • Date of Stay: December 2015
  • Source: VRBO, from HomeAway
Owner's Response: Thank you so much for taking the time to write a review the day after your departure! I know it must be a busy time do so we really appreciate the effort. You bring up two points that i like to have guests address because they can do so better than we can. Windwardside Guest Cottage was a special place for us to build because we had a particular intent. We wanted to build a small cottage that still had plenty of charm and comfort and we loved the challenge. We wanted visitors to St. John to be able to enjoy a very special place without blowing their budget. We feel a lot of pride in providing a compact space with a charming old time Caribbean feel, a great view. four poster bed and private hot tub. I am also glad that you mentioned the need to discourage insects. In the states it is common to leave sugar bowl on the counter but here.... oh no. Tropical rules apply. If it is open, put it in the fridge is you don't want ants! Even if you do want ant put it in the fridge because the next guests might not:) Thanks for your visit! Susan
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Nearest Airport
20 Miles
St. Thomas
Nearest Barpub
1 Miles
Shipwreck Landing
Nearest Ferry
8 Miles
Cruz Bay
Nearest Restaurant
1 Miles
Shipwreck Landing
Nearest Beach
2.5 Miles
Salt Pond Bay
Car: necessary

Remote and quiet setting, three quarters of a mile up dirt road with very little traffic. Beautiful view of Coral Bay and nearby islands. Near to beaches, shops restaurants, hiking trails and boating. Shares no facilities with other home on property except parking area.


Prices & Availability

Prices for this holiday cottage in Estate Calabash Boom, St John

Rental Basis:
per property
Manager accepts payment in:
Convert Currency
Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly Event Price
Low Season 2018
16 Apr 2018 - 14 Dec 2018
7 night minimum stay
for 7 nights

Additional pricing information

There is an additional 12.5% hotel tax that will be added to the weekly rate.
12/15 - 4/15 $1610/weekly (2 Guests).
4/16 - 12/14 $1330/weekly (2 Guests).

Hotel tax in the Virgin Islands is increasing to 12.5% as of January 1, 2016.
For larger groups the guest cottage can be rented along with the neighboring Windwardside Main House.
For that option, or to see our other cottage for two, Sago Cottage, please see our additional listings on the St. John page.

Check or money order. 50% at time of reservation. Balance due 30 days before arrival.

Manager's Cancellation Policy

Please ask the manager or check their rental agreement when booking the property.

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