from $190 /per night
Enter dates for availability

Adorable studio with a great view, hot tub, very quiet location

HomeEscape Sleeps
Sleeps 2
HomeEscape Bedrooms
1 Bedroom
HomeEscape Bathrooms
1 Bathroom
HomeEscape Bathrooms
Min stay 7
from $190 /per night

Adorable studio with a great view, hot tub, very quiet location

HomeEscape Sleeps
Sleeps 2
HomeEscape Bedrooms
1 Bedrooms
HomeEscape Bathrooms
1 Bathrooms
HomeEscape Bathrooms
Min stay 7 Nights
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. The lush tropical plantings, built in privacy screening and the orientation of the buildings seclud ... more +
Property Type: Studio
Location Type: Near The Ocean
Size: 300 SQ-FT
Children Welcome
Wheelchair Accessible
Minimum Age Limit for Renters
Senior Adults Only Community
Long Term Renters
Events Allowed
Internet Access
Air Conditioned
Wood Stove
Fitness Room / Equipment
Living Room
Washing Machine
Clothes Dryer
Linens Provided
Towels Provided
Hair Dryer
Iron Board
Music Library
Premium Channels
Wireless Internet Access
Video Games
Video Library
Board & Card Games
Pool Table
Coffee Maker
Kitchen Utensils
Garbage Disposal
Communal Pool
Private Pool
Hot Tub
Heated Pool
Indoor Pool
Car Available
Private Chef
Bar/Night Club
Charter Boats
Deep Sea Fishing
Horseback Riding
One queen sized for poster bed with water view

Standard Rate

Per Night
Weekend Night
Minimum Stay
Sunday to Sunday rentals. Plus a USVI hotel tax of 12.5%.
Payment Policies

The owner of this property requires full payment to reserve.

Fees & Taxes
Lodging Tax: 12.5%
Maximum Stay: 7 Days
Check-In: 4:00 PM
Check-Out: 10:00 AM
Deposit Requirements
50 percent at time of booking. Balance due 30 days before arrival.
Cancellation without penalty only if we are able to book the same time period
Susan Brierley
Speaks: English
Member Since 2015
This property was purchased in 1996
About Susan Brierley
My husband Paul and I are long term residents of St. John. We love to travel and our travel almost always focuses on finding beautiful natural surroundings. My husband (a retired builder on the island) and I designed Windwardside and Sago Cottage (calabash Cottages) with the intention of providing that to like minded guests. We care very much about preserving the beauty of Coral Bay. An import ... more +
Why This Property?
Our goal in constructing Windwardside 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 t ... more +
Unique Benefits
Location: Coral Bay, St. John, U.S. Virgin Islands. Windwardside Guest Cottage is located in quiet seclusion with mesmerizing views of Coral Bay, nearby islands and the Caribbean Sea. The house is situated two thirds of a mile up a little used road in Coral Bay. Surrounded by tropical plantings and marvelous vistas, you are still just a short drive to a cool splash in Salt Pond Bay or other equall ... more +
Roberta M
February 29th , 2016
Wonderful Vacation
Date of Stay: December 27th , 2015

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! Recommended for: Sightseeing, Adventure Seekers, Romantic Getaway My 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


Matthew b
December 28th , 2015
Great Honeymoon stay
Date of Stay: December 20th , 2015

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! Recommended for: Adventure Seekers, Romantic Getaway My 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 ants put it in the fridge because the next guests might not:) Thanks for your visit! Susan


Shayla L
February 20th , 2015
Stay here if ya wanna have an amazing adventure!
Date of Stay: September 28th , 2014

t has taken me a bit to get on here and leave my review..mainly because I miss this place so much. It is truly breath taking,gorgeous,romantic,adventurous,charming,convienent, spaciousand almost perfection! My husband and I loved the drive up because it was just fun and felt like we were staying off the beaten path. I seriously miss how I would laugh going down the hill, and after the first day my husband was a pro driving up and down. Bottom line, if you want one of those high up gorgeous views, you have to stay up in the hill tops to get those amazing pictures! And trust me this is the place to stay! The grounds are just , wow. All the flowers and greenery made you feel like you were in the jungle. I loved waking up every morning and drinking coffee on the porch , staring at the rising sun and being in awe of the views. There are bugs here though, so be mindful...staying here is being closer to nature and if you are looking for a high end resort feel I would go blow your money at the hilton...but if you want a fantastic deal for what you get and to be surrounded by absolute nature with still outstanding natural luxury experience, then please stay here! It made our trip so much fun staying on the more private side of the island. Yes there is alot to do on the boat dock side, but this side of the island has so much more breathing can visit beaches that have nobody on them , seriously ! And there is a great conveince store right before you turn into the neighborhood, it just opened last year and the owner is a really great guy. He actually has an IOU when I forgot my money he let me take my groceries as long as I would pay him back before out trip ended ( I did duh lol ) ...cannot find that in Texas anywhere! And besides that there are some great resturants, but Aqua Bistro was our favorite. We ate there 4 times and loved it everytime. And the drive to the other side of the island is just absolutly first we would drive thru the middle but after a few days we switched to the right side of island, going along the beaches...get to know your maps and do it both ways, it really is a great drive across....and please plan your beach visits accordingly. I made a loose schedule for each day ( it may have been laminated ) and by doing so we were able to visit and enjoy SO many beaches...also I highly recommend going in off season...yes some resturants will be closed, but you will be on a island that feels almost empty and that is a really amazing feeling.... it made it more romantic, less stressful ...and easier driving cause there was almost no traffic! ...back to this property.... it is wonderful...tree frogs at nightime, the outdoor shower which is so beautiful , the huge courtyard, the hot tub we spent everynight in (we rigged our laptop and set it on chair and watched movies every night out there ) , the full sized kitchen was such a plus....and the absolute best part was the customer service from the managment team!! Please I urge you if you stay here ( you really should do this anywhere you stay) and have any issue contact them and I promise you these guys will be there to fix or help out in any way. We had one small issue and literally in an hour I recieved a phone call (in suite landline) and they were on it immediatly. Truly great group of managment and because of this place and their team my husband and I had an amazing wedding anniversary was just perfect in so many ways and I tear up thinking about it !! P.S I am adding pictures of not only the grounds but also some of the beaches, so that you can see what the beaches look like during off season...I will trade in every resturant being open for peopless beaches any day! Makes for much better pictures ; ) Management Response Mar 20, 2015 Thank you for your review. I agree with you that there are definitely some advantages to being here during the off season. The quiet beaches are so incredibly peaceful. We always make sure guests know about our bumpy road but like you mentioned that's where the beautiful views are and it is all part of the adventure. Fortunately, it is only 2/3 of a mile but it can seem a bit longer. I am very fortunate to have such great support staff and I am happy that your maintenance issue was taken care of promptly. That's our goal. I hope that you make it back to Windwardside in the future. Thanks for trusting us with your vacation time. All the best- Susan


Therese & Mikael
January 18th , 2015
Date of Stay: November 24th , 2014

The cottage was absolutely a paradise. It was tiny but clean and maintained down to the smallest detail. Breakfasts on the balcony with the stunning view will we never forget. We have never been so welcomed and taken cared off. The whole arrangement with taxis, pickup and car rental was excellent. We will be back!!! Thanks for everything!!! Recommended for: Girls Getaway, Age 55+, Romantic Getaway My Response Thank you, Therese and Mikael. We are honored to have guests come from so far away to stay at our cottage. I am glad that we were able to live up to your expectations. Thank you for taking the time to review that cottage. I hope that we see you again. Susan


Dick (Maryland)
December 29th , 2014
Great surprise birthday gift!
Date of Stay: December 14th , 2014

This cottage was all we expected from the exciting pictures on the web. It did not disappoint. The view was even better than expected. Everything was clean and well organized, with many extras helpfully available. The location on the quiet side of the island a dream, with excellent restaurants nearby. The transportation from the St. Thomas airport to the St. John ferry and back, the car rental, a leisurely stop at the one big supermarket, and the taking us to the cottage upon arrival were all arranged for us as promised. The greeter was terrific! She guided us through all this with patience and many suggestions and information that proved very helpful later. The car rental agency that was arranged was also helpful, letting us park there when visiting Cruz Bay and even taking us back to the ferry at the end when he saw how much luggage we had. Four wheel drive is necessary to get to the cottage (Mr. Toad's wild ride up the mountain on dirt roads), but the view and quiet are well worth it (just toads at night, roosters in the morning, and stars overhead.) And four wheel drive (the island is awash in Jeeps) is necessary to get to the great isolated beach at Little Lameshur Bay for swimming and snorkeling. They promised a 5 star vacation, and it was! Thanks to all. Owner's Response: Dear Richard, I am so glad that your birthday surprise for Steve's 60th was a hit. Also, I am happy that you got to explore "little" lameshur. It's one of my favorite snorkel spots that I always take my family to when they visit. Thank you for staying with us and taking the time to write a review. All the best- Susan


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