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This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation
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3 BR 2 BA Sleeps 12$214 avg/night3 night min stayThis property’s not located within the current map view
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$249 avg/night2 night min stayThis property’s not located within the current map view
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4 BR 3 BA Sleeps 8$1,016 avg/night4-7 night min stayThis property’s not located within the current map view
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$215 avg/night3 night min stayThis property’s not located within the current map view
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$400 avg/night3 night min stayThis property’s not located within the current map view
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$205 avg/night2 night min stayThis property’s not located within the current map view
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$632 avg/night1-4 night min stayThis property’s not located within the current map view
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$129 avg/night1-15 night min stayThis property’s not located within the current map view
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3 BR 1 BA Sleeps 6$262 avg/night2-7 night min stayThis property’s not located within the current map view
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$307 avg/night1 night min stayThis property’s not located within the current map view
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$995 avg/night2-4 night min stayThis property’s not located within the current map view
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$736 avg/night2 night min stayThis property’s not located within the current map view
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$200 avg/night1 night min stayThis property’s not located within the current map view
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$283 avg/night7-90 night min stayThis property’s not located within the current map view
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$393 avg/night1 night min stayThis property’s not located within the current map view
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$405 avg/night2-6 night min stayThis property’s not located within the current map view
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$708 avg/night3 night min stayThis property’s not located within the current map view
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1 BR 1 BA Sleeps 2$173 avg/night3-30 night min stayThis property’s not located within the current map view
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$238 avg/night2-30 night min stayThis property’s not located within the current map view
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$275 avg/night15-30 night min stayThis property’s not located within the current map view
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View listing for price3 night min stayThis property’s not located within the current map view
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2 BR 1 BA Sleeps 4$204 avg/night7 night min stayThis property’s not located within the current map view
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2 BR 1.5 BA Sleeps 4$350 avg/night4 night min stayThis property’s not located within the current map view
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$250 avg/night7 night min stayThis property’s not located within the current map view
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$333 avg/night1 night min stayThis property’s not located within the current map view
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$185 avg/night2-3 night min stayThis property’s not located within the current map view
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$1,200 avg/night1 night min stayThis property’s not located within the current map view
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$243 avg/night3-6 night min stayThis property’s not located within the current map view
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$643 avg/night7 night min stayThis property’s not located within the current map view
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$567 avg/night4-7 night min stayThis property’s not located within the current map view
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4 BR 2.5 BA Sleeps 8$500 avg/night7 night min stayThis property’s not located within the current map view
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$305 avg/night3 night min stayThis property’s not located within the current map view
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$700 avg/night3 night min stayThis property’s not located within the current map view
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$239 avg/night2 night min stayThis property’s not located within the current map view
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$80 avg/night1 night min stayThis property’s not located within the current map view
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$104 avg/night1 night min stayThis property’s not located within the current map view
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2 BR 1 BA Sleeps 4$143 avg/night1 night min stayThis property’s not located within the current map view
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$114 avg/night2 night min stayThis property’s not located within the current map view
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$199 avg/night2 night min stayThis property’s not located within the current map view
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$66 avg/night1 night min stayThis property’s not located within the current map view
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$80 avg/night1 night min stayThis property’s not located within the current map view
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$311 avg/night30 night min stayThis property’s not located within the current map view
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View listing for priceThis property’s not located within the current map view
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View listing for priceThis property’s not located within the current map view
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$417 avg/night7 night min stayThis property’s not located within the current map view
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1 BR 1 BA Sleeps 2$156 avg/night6-13 night min stayThis property’s not located within the current map view
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$286 avg/night7 night min stayThis property’s not located within the current map view
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View listing for priceThis property’s not located within the current map view
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View listing for priceThis property’s not located within the current map view
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3 BR 2 BA Sleeps 4$166 avg/night4-31 night min stayThis property’s not located within the current map view
Recent Long Island reviews
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"My family looks forward to our summer vacation on Shelter Island mostly because we get to stay here. Little Gem is really special--a sweet little cottage perfect for us, a family of 4 from NYC with two little girls (ages 5 and 1). Joan keeps a tasteful, clean, quaint space. We spend our mornings in the front yard, lounging in the hammock or running around with the kids. Afternoons are spent at Wades Beach, just a mile down the road. Dinner is either at Commander Cody's just around the corner or something made off the grill. The kitchen is well equipped with all the essential items to cook every meal. Joan is an attentive host--this year we rented the last week of summer to find the gas tanks for the grill empty. Joan was readily available when we reached out to her about the issue and quickly refunded us for refilling the tanks the next day. By the end of our stay, we always wish we could stay longer. We are already mapping out our return next summer. Thanks Joan for another wonderful stay!"
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"Our stay at this home was fantastic. The condo was neat and nicely decorated. It was close to Gosman's Dock for shopping, dining and boat gazing. There was a great pool which we were lucky enough to enjoy due to good weather. The very best part, though, was the spectacular sound view and the killer sunsets. Such a great experience and looking forward to the next time!"
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"I recently booked to stay with 3 girlfriends. The cottage is extremely comfortable and well appointed. It's a short bike ride or drive to local wineries, brewery and restaurants. It's a short walk to the beach as well. The complimentary wine upon arrival was much appreciated as we sat in the beautiful backyard enjoying the scenery. I must mention that the Bose system was a huge bonus as well. I would definitely book this property again next year (or sooner)."
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"Our family had an amazing time renting this property. The house was so spacious and the grounds were beautiful! our son had a blast running around on the huge lawn! Everyday we had deer that would great us at night while we were cooking or dining out on the deck. The house had so much room...the rooms are at one end of the house so when the kids went to bed they would not hear us in the kitchen/great room area or on the deck outside. The location was ideal too! You get so much privacy with this house but then you are a quick walk or bike into town. We enjoyed going to the beach everyday which is only a quick car ride, for the kids, or a walk down the hill. Chris was great to deal with and was very accommodating. We will definitely be looking into renting next year to continue our family tradition! Thank you for everything Chris!"
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