Windwardside Guest Cottage

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.

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."

I'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!

This was our second time to windwardside Guest cottage and we had another amazing experience. The view, the hot tub, the island, everything was great. Susan, Diane, and Margaret were fabulous with everything. Hope to be back again soon!

Emily and Zack

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!