Windwardside Guest Cottage

1 Bedroom, 1 Bath, Hot Tub
Sleeps 2
$1330 Low Season (Apr 16-Dec 14)
$1750 High Season (Dec 15-Apr 15)

Please note: We never advertise on Craigslist. We will never request guests to wire money directly to our bank accounts.
If you should encounter either of these please contact us directly to avoid fraud.

Windwardside Guest Cottage

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.

Guest cottage hot tub

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.

Cozy, cheerful interior

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.

Kitchen

Bedroom

In short Windwardside Guest Cottage offers a serene location, fabulous view, charming furnishings, a private hot tub, kitchenette and bbq, plus dedicated staff that 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 our former guests. We hope to host you on our next visit to St. John.

Read Reviews

Ocean view from porch

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.

Garden

Coconut Palm

garden path

garden

Dine on the covered porch

Covered porch

Covered porch

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).

Additional Images

Nearby Beaches & Sights

Amenities

  • Hot Tub
  • Snorkel Gear
  • Beach Chairs
  • Cooler
  • Beach Umbrella
  • BBQ
  • CD & VCR Player
  • Phone
  • Fresh Flowers
  • Robes, All Linens & Towels
  • Safe for Valuables
  • Wi-Fi Internet

Activities

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.

Arrival

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.

For details about our our policies, reservations and travel suggestions please read our FAQ.

Availability Calendar for Windwardside Guest Cottage

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Guest Reviews for Windwardside Guest Cottage

Wonderful Romantic Getaway – Picturesque, Private and Beautiful
Christopher H.
10-29-2013

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.

THE PERFECT SECLUDED GET AWAY – BEST ISLAND VIEWS POSSIBLE
Snorkel Man
10-19-2013

MY WIFE AND I HAVE TAKEN SEVERAL CARIBBEAN TRIPS AND THIS WAS OUR ABSOLUTE BEST.

ALL THAT THE OTHER REVIEWS SAY RE THE TRIP ARRANGEMENTS SUCH AS PLANE CONNECTIONS, JEEP RENTALS AND STAFF ATTENTIVENESS ARE VERY TRUE.

THIS COTTAGE IS VERY SECLUDED, PERFECTLY SIZED AND FEATURED TO MAKE YOUR STAY THE BEST IT COULD EVER BE. ESPECIALLY THE HOT TUB - SO VERY PRIVATE AND TO LOOK UP AT THE STARS WHILE LAYING THERE WITH A DRINK IN HAND IS JUST THE BEST EXPERIENCE ONE COULD WISH FOR - GENTLE BREEZES KEEP YOU COOL AND COMFY WHILE SLEEPING AT NIGHT AND THEN TO WAKE UP TO THE ISLAND VIEW - OH MY !!!

THE SNORKELING IS TO DIE FOR - VERY MANY LOCATIONS WITH OVERFLOWING OCEANLIFE FROM RAYS TO TURTLES TO BARRACUDA ( NOT A CONCERN ) TO STARFISH TO OCTOPUS TO SHARK - MORE THAN ONE COULD HOPE FOR.

WE HAD SUCH A WONDERFUL TIME WE SO HATED TO LEAVE - WE WILL BE BACK AND STAY LONGER EVEN THAN WE DID THE FIRST TIME.

WE CANNOT SAY ENOUGH GOOD RE ALL THE FEATURES OF THE COTTAGE, THE STAFF, THE FOOD ON TH ISLAND, THE SNORKELING AND THE FRIENDLY FOLK ON THE ISLAND.

PLEASE PLEASE DO NOT PASS UP THE CHANCE TO SEE ALL THAT THE COTTAGE AND THE ISLAND OF ST JOHNS - US VI - HAS TO OFFER - YOU WON'T REGRET COMING TO SEE THIS ISLAND PARADISE WHICH BYW IS VERY EASY TO GET TO BUT OH SO HARD TO LEAVE !!!

TODD / LAURIE

The Windwardside Guest Cottage is Wonderful!
Binger and Lillie
03-06-2013

We just returned from a wonderful week long stay at the Windwardside Guest Cottage (Feburary 24-March 3, 2013). The cottage is even nicer then the pictures on the web site! The view from the porch looking down on Coral Bay is incredible. Diane and Susan were both terrific to communicate with prior to our arrival and made sure we had all the information we needed. Diane is just a local phone call away if you need any information during your stay. The cottage is very clean and well maintained and fully stocked even down to beach towels and snorkeling gear. I was pleased to learn that some of the electrical energy comes from five solar panels mounted on top of the porch – very Green! You will need a four wheel drive Jeep to get to the cottage and Diane took care of arranging that for us as well when we made our cottage reservation. Bruce met us in Coral Bay and made sure we got to the cottage as the first time up the road is a bit tricky. Bruce also answered our questions about the cottage and offered his insights on good snorkeling spots. The WIFI worked great in the cottage and so we streamed NetFlix movies on our Kindle at night. Pack your swimming suit, tee shirt, shorts, sun glasses and sun screen and head over to Waterlemon Cay, Haulover Bay, Salt Pond or Hansen’s Beach for some great snorkeling and Miss Lucy’s or The Shipwreck for fun dinners. Don't forget to have at least one lunch at Skinny Legs! Sure hope we can stay at the Windwardside Guest Cottage again in the future! Special thanks to Diane for her great communications!

Best little cottage on the Island
Jamie and Mona
02-28-2013

Our trip to Calabash Cottages couldn’t have been better from start to finish. Prior to departure, Susan and Diane made sure that all of our travel arrangements were coordinated. They arranged for a private driver to pick us up at the St Thomas airport to drive us to the Red Hook ferry dock and for a second driver, or greeter, to meet us at the Cruz Bay, St John ferry dock. And, when I phoned Diane at 7am on the morning of our flight and told her that we would be catching an earlier flight, she still managed to rearrange all the pick-ups and accommodate our last minute travel change. Our greeter in St. John was Bruce. He took us to the Courtesy rental car company which gave us a discount because we booked it through Susan and Diane. After picking up our rental Jeep, he then had us follow him to a local grocery market and gave us suggestions as to what to buy and where. After waiting for us to shop, he gave us some driving tips for the island and we followed him to Coral Bay and made another stop at a local market in Coral Bay so that we would know where to shop on the other side of the island. The drive up to the cottage is not for the faint of hearted, but it is totally worth it. Upon reaching the cottage, we were amazed at the quaintness, the view, the privacy, the top notch attention to detail; it was perfect. Bruce showed us around and made sure that we knew where everything was. And to top off this first class pick up treatment, Bruce spent the extra time to tell us about some of the best snorkeling locations, the best eating locations, the best off the beaten path beaches, the best hiking trails, the best times to go, etc… making sure that we really were ready for our trip.

During our trip, we made sure to get up early and hike the island and visit every beach. We hiked the Lind Point Trail early in the morning to have Solomon Beach and Honeymoon Beach all to ourselves for quite a time and then hiked Margaret Hill and Caneel Hill to witness the amazing views. We hike the Lameshur Bay trail all the way to Reef bay, enjoying a strenuous hike and the ruins along the way (and back again!) and enjoying the entire bay to ourselves. The south beaches of Salt Pond Bay and Little Lameshur Bay are just as great as the famous north shore beaches and less crowded. We did go to Hawksnest Bay and Trunk Bay early in the morning and enjoyed the hike to Peace Hill to see these views of the north shore bays from there. We hit the Brown Bay Trail and the

Paradise Found!!!
Julie G.
11-02-2012

My husband and I visited St. John for the first time and had an amazing vacation! We are already planning our next trip! The Windwardside Guest Cottage was the perfect place for our romantic getaway! It was clean, comfortable and Susan and Diane were so helpful and accomodating from day one of booking my vacation. We had a problem with the water going out and they were there to fix it within 10 minutes of our call-what wonderful service! I loved waking up to the spectacular view from our cottage-it really is breathtaking! The outdoor shower was awesome too! There are some wonderful restaraunts nearby and its a short drive to many beaches! It was really relaxing to end our busy day of exploring to get in the hot tub and look up at the stars. If you are looking for a small, cozy romantic place to stay on the island, look no further. This little cottage is perfect!

Our Response
Thanks for such a lovely review. I am very happy to hear that you enjoyed your stay with us. We look forward to seeing you on your next trip. Susan

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