We very much enjoyed our stay at Jessica's place in Shelter island. The house is in a very quiet, wooded area and the backyard is almost completely enclosed by tall trees so you get maximum privacy and quiet. The pool is big and heated with a lovely deck, very comfortable lounge chairs, a big umbrella and lots of fun floats - even a diving board! The only downside because of all this beautiful woodedness is bugs! So many mosquitos. So bring the bug spray and we used citronella candles when we ate upstairs on the deck and also when lounging by the pool. The outdoor eating and lounging area upstairs is very pretty and comfortable. The house was big inside, living room and beds very comfortable. TVs in most rooms and tons of books and games in the basement. Would have loved some more large plates and cups as well as plastic cups for by the pool, but otherwise kitchen was well equipped. The owner and house manager were communicative and helpful. Would definitely recommend the home and area.
We loved Wade's Beach, the nearby nature preserve (again, bring bug spray), and we ate at Ram's Head, Vine Street, Isola and Fortino's (in Greenport) - all delicious. Slice down the road had good take out pizza. Salt restaurant location is gorgeous, food just OK. Cool outdoor bar and food truck with live music next door. Everything on the island is like an 8 minute drive or less, love it!