There are a multitude of quaint hotels and bed and breakfasts' on Shelter Island, however, we found a true gem.
We rented the absolute charming upper half of the Beech Tree House. Our floor featured three bedrooms, all with beds big enough to fit two per room, a large bathroom, a small sitting area, a living room and a full kitchen. Perfect for a weekend out of the city with a group of friends. Note: The bottom half of the house is a one bedroom with a living room.
The property was beautiful, featuring a large lawn surrounding the house and a multitude of outdoor seating options, for complete relaxation.
I would highly recommend The Beech Tree House to anyone heading to Shelter Island, and may in fact be back again this fall with the same group I went with originally. We had such a lovely time and it was nice to have the comforts of home while away.
Divided by 6 (the maximum guests due to beds), the cost for a full weekend was under $60 a person. A FANTASTIC deal and well worth much more than that. Plus, the owner of the Beech Tree House (and Azalea Bed & Breakfast - a separate option) is also the owner of the Shelter Island cab company, making transportation a breeze!
As night settled around us we actually kicked it back in the room. This is a rare occassion, we usually only use a hotel room for the pure reason as a home base. The rooms were so inviting that par-laying there was actually like doing something. Tapping the case of bottles from the North Fork wineries we faded the night into the next day, seamlessly.
Perched atop the hill right when you depart the NorthFerry, The Chequit Inn bares its barrel-chested facade. Grandpa has been around since 1872, so his tastes are well developed. As i scoured the net for a place to lay our heads, my main priorety was 1.good food, relying heavily on Long Island product, and 2. a extensive wine list, shedding heavily on the Long Island selection. With a viewable menu on their website, they hooked and reeled me in. Our room was great, no television to distract my peace, a outside porch with two sunning lounges, full bathroom, and a great paint job. I painted houses for years in the Hamptons so I do pay close attention to the application of their paint. I noticed there was no paint tape used, just a fine cut where ceiling meets wall. Origional detailing outlined all doors and windows also painted professionally. A paintjob can shed light on the care that a place puts into itself. There is a large restaurant on premises with outside dining. Even if you do not stay, try the food here, it's excellent.
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