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

  • Bedrooms
  • Bathrooms
  • Sleeps

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 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.
covered porch.
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.
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.
When you are enjoying the view from the deck you will have an unbeatable view of the ocean. However, there is also an abundance of lush tropical plantings that provide complete privacy from the neighboring villa, Windwardside Main House.
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 equally inviting white sand beaches. Restaurants, shops and watersports are all available within two miles in Coral Bay. The main town on the island, Cruz Bay, is located 8 miles away. The airport is in St. Thomas which is reached via a twenty minute ferry ride. (Ferries leave every hour on the hour and cost $7 each way)

We are happy to make suggestions for activities that suit your interests. When you arrive at your cottage we will go over a map of the island and point out the best beaches, hiking trails, snorkel spots, etc. Most activities can be arranged once you are on island but if you are planning a day on the water you may want to arrange that in advance. Consider Busy Bee Charters “Lap of St. John” on Wednesday for a really fun trip that departs right from Coral Bay.

Windwardside is managed by on island owners. We will meet your ferry 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.


Virgin Islands, US Virgin Islands, St. John

Address: 28-13 Calabash Boom St. John
Zip or Postal Code: 00830
Latitude/Longitude: 18.33038769813498 / -64.70888077636721
Nearest AirportSt. Thomas (STT)25 miles
Nearest BeachSalt Pond Bay2.5 miles
Nearest FerryCruz Bay Dock9 miles


We meet guests upon arrival to show them out to the cottage.


Coral Bay


Property Type:
Guests provide meals
Floor Area:
6,458.35 sq. f.
Location Type:
1 Bedroom, Sleeps 1
Queen Beds: 1
1 Bathroom
Baths: 1
Showers: 1
Sinks: 1
Toilets: 1
Off-road parking
Hot Tub
Activities guide
Beach chairs
Beach towels
Dining guide
Indoor hot tub
Outdoor hot tub
Private location
Alarm clock
Bathroom tissue
Ceiling fans
Coffee maker
Cooking utensils
DVD player
Filtered water
Iron and board
Paper towels
Deck furniture
Gas grill
Pet Friendly: No
Smoking Allowed: No
Child Friendly: Yes
Long Term: No
Elderly Accessible: Yes
Wheelchair Accessible: No
Other Services:
Cleaning inclusive
Linens provided
Towels provided
Local Activities:
Horseback riding
Scuba diving
Area Services & Attractions:
ATM / Bank (2 miles)
Duty free shops (9 miles)
Rainforests (6 miles)
Restaurants (1 miles)
Ruins (4 miles)
While we are not wheel chair accessible we have many elderly guests. There are steps involved but we would not want to say that automatically made it unsuitable for the elderly. I could be in big trouble with my mom.


June 2024
September 2024
November 2024
December 2024
February 2025
March 2025
April 2025
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Rental Terms

 Check-in Time: 4:00 PM
 Check-out Time: 11:00 AM
  Payment Options: Checks
Security Deposit: None
Rental Agreement:
50% of payment is due via personal check when reservation is made. The balance is due 30 days before your arrival. Payments are fully refundable if we are able to find another guest to fill your vacancy. We do not charge service fees, reservation fees or cleaning fees.

on Apr 07, 2016
Wonderful Vacation

ur 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

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

on Apr 07, 2016
Great Honeymoon stay

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

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 ants put it in the fridge because the next guests might not:) Thanks for your visit! Susan

on Apr 07, 2016
Great surprise birthday gift!

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.

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

on Apr 07, 2016

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

Owner's Response:

hank 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

on Apr 07, 2016

m happy to report that your cottage has a magical quality. What an amazing, relaxing (albeit daily snorkeling, hikes and further adventures) lovely way to visit St. John. Windward Guest Cottage quickly became my new favorite place to stay! The pictures on the Homeaway website showed a tropical paradise but what we found here was so much more.
Thank you for the wonderful amenities. The house was well equipped for a comfortable stay. And anyone reading this has already been stunned by this view! No words...
We will definitely come back!

Owner's Response:

It was a pleasure meeting you both. So glad that you enjoyed your week at the cottage. We hope you make it back for another stay. Thank you for spending your vacation with us and sharing your experience.

on Apr 07, 2016
Stay here if ya wanna have an amazing adventure!

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 ; )

Owner's Response:

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

on Apr 07, 2016
Take me back there, right now.

We had such a glorious time. The cottage is tiny but wonderful -- clean, airy, bright. There's no A/C because it's designed with windows on all sides and a ceiling fan to help the cross-breezes along. We were comfortable in mid-May. It felt like much more of a real island experience than staying in a resort.
I was nervous about privacy because this cottage is attached to a larger house. They told us the plantings would provide privacy, and they really, really do. The entire place is cloaked by beautiful tropical plantings, with the exception of the view straight out to the ocean. The only time you'd see other people is on the path to the shared parking lot, which crosses directly in front of the cottage by the double screen doors right in front of the bedroom. There are curtains you can pull in front of the doors, though.
The garden shower is very private. The wall around it is probably 7 feet tall, with vines and plants coming down the walls. It was awesome.
The views pictured on this website are not exaggerated, btw. I was pretty sure the photos were prettified in some way, but the view is exactly as pictured, and I have a bunch of photos on my camera to prove it. Basically, that's what you see when you're sitting up in bed.
They're not exaggerating about the road, either. The first time we drove up it, we were both white-knuckled. By the end of the week, we were rocking and rolling down that road like old pros. It was great. A little tutorial from the car-rental agency didn't hurt, either.
We used the grill, but we never got around to using the hot tub -- we'd rather have spent our time on the beach. The WiFi was not quite strong enough to stream Netflix, but there is a small TV with a DVD player, so I'd bring DVDs if you want to watch movies at night.
We liked Coral Bay way better than Cruz Bay, the more populous town on the other end of the island. There are far fewer people and more donkeys/chickens in the road, which was amusing, and just as many great beaches. We went over to the west end to visit, but we always ended up preferring Coral Bay.
Word of warning: If you're going to the islands in May or later, be sure to bring plenty of DEET, because the mosquitoes will be out in force, including in the garden shower. As one local told us, "Better spray than dengue."

Owner's Response:

Thanks for posting about your stay at Windwardside Cottage, Sarah. I'm glad to hear that we lived up your expectations. I especially appreciate your addressing the issue of privacy from the main house. It means much more to potential visitors to hear this from a former guest than directly from us. Sorry- that your trip was during one of the "buggy". It isn't necessarily an issue related to the month of the year. When we get a big rain after a dry period mosquitoes tend to hatch out 5-7 days later. Fortunately, the "bloom" does not usually last very long. Thanks again for staying with us and we hope to see you again. Susan

on Apr 07, 2016

This was our first visit to St John and now that we’re in love with the island we can’t imagine staying anywhere other than the Windwardside Guest Cottage - except perhaps another Calabash Cottages property. We just can’t gush enough about this sweet little bungalow. Its setting is spectacular; the view will knock your socks off! A teeny note of caution for those less adventurous, the last mile approaching the cottage is slightly intimidating (steep, quite a drop down [thus the fabulous view!] and mostly not paved/bumpy). However, don’t let that sway you – you get used to it by your 2nd or 3rd try and it’s worth it.
The cottage was perfectly appointed for two. Everything you’ll need for your stay is there. The little galley kitchen will surprise you by how well equipped it is, between it and the grill we were very set to have most of our dinners in, and we’re not talking PB&J here. The cottage was spotless and extremely well cared, particularly given how rough an island environment can be on metal, wood, etc. It appears as if it is tended to regularly.
The level of service from this team was top-notch. Margaret & Diane answered all of our pre-arrival questions & provided great tips for our stay. Beth (aka Yoga Beth) met us at the ferry dock & generously spent about 2 hrs with us. In addition to what was promised (ferry pick-up, rental car retrieval, grocery stop in the big city, follow-me to the cottage), Beth took us to the National Park Visitor Center so we could pick up our tickets for a hike the next morning. She also provided us some wonderful “local’ tips on beaches for snorkeling and restaurants not to miss. Beth never once made us feel rushed; she really introduced us to the concept of island time. Oh almost forgot Warren from Dynamic tours, the car service from the airport to the ferry in St Thomas which was recommended & we highly suggest using it. It made our arrival & departure so smooth. Warren was warmly welcoming & completely reliable, there for us at the airport despite that our flight was over an hour late & then he called at the end of the week to find out which ferry we were taking from St John so that he’d be waiting our arrival. Lastly, Susan (the owner?) called us the last night to be sure our stay had gone well. Really, this is stellar service that is rare to find these days.
Thank you Calabash Cottage team. …..and for prospective future guests reading this: don’t hesitate, this place is a gem!

Owner's Response:

Thank you, Jon and Lynne, for your detailed review. I know how helpful it is to future guests to hear from people who have already stayed with us. I am so glad that that you enjoyed your week. I will pass on your appreciation to the rest of the team. We hope to see you on your next visit to St. John. Thanks again for staying with us. Susan

on Apr 07, 2016
Breathtaking views, perfect home in paradise”

am writing this a year later, but I had to give a raving review about this place! My husband and I came here for our honeymoon, and are longing to go back! Everything was incredibly clean, beautiful, and well taken care of. The view was indescribable, and the jeep rental was great! All of our transportation from the dock to our jeep rental place and then to our place was perfectly planned. We raved about this place so much that our friends decided to spend their honeymoon in one of the Calabash Cottages as well!! Thank you for providing the perfect place for a honeymoon in paradise!

on Apr 07, 2016
Wonderful Romantic Getaway - Picturesque, Private and Beautiful

Surround yourself with the natural beauty of Coral Harbor water and the lush green mountainside into which this lovely cottage has been built. We stayed for a week in this romantic getaway. We took multiple pictures from the four-poster bed of the water below, just to show how beautiful this setting was. The view from this cottage is outstanding, and as the ad says, we watched many sailboats entering and exiting Coral Harbor. We also watched a little hummingbird come back time after time drinking from the beautiful flowers growing just below the deck. Whether you're showering, enjoying champagne in the hot tub, or eating dinner on the deck, you have the same view of the hillside and the harbor below. If you're looking for a romantic getaway, away from the hustle and bustle of the crowed hotels and city streets, this quaint tropical cottage is definitely the place.
Recommended for: Sightseeing, Girls Getaway, Adventure Seekers, Age 55+, Romantic Getaway


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