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Shelter Island Short Term Vacation Rentals(33)

33 Results
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 14 night min stay
1 Review
$5,000 - $5,833
per week
14 - 31 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
14 - 31 night min stay
  • 6 BR,
  • 7 BA,
  • Sleeps 14
3 night min stay
(8)
$12,500 - $25,000
per month
30 - 31 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
30 - 31 night min stay
(3)
$425 - $575
per night
2 - 6 night min stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
2 - 6 night min stay
(6)
$500 - $575
per night
2 - 6 night min stay
  • 4 BR,
  • 1 BA,
  • Sleeps 8
2 - 6 night min stay
(3)
  • 3 BR,
  • 2 BA,
  • Sleeps 10
3 - 28 night min stay
1 Review
$2,275
per week
7 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
(3)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 night min stay
(4)
$350 - $571
per night
2 - 7 night min stay
  • 3 BR,
  • 1 BA,
  • Sleeps 8
2 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 night min stay
$1,500 - $3,500
per week
7 - 31 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
7 - 31 night min stay
$2,650 - $6,250
per week
7 - 14 night min stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
7 - 14 night min stay
1 Review
  • 6 BR,
  • 4 BA,
  • Sleeps 12
3 - 5 night min stay
2 Reviews
$500 - $600
per night
3 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 - 7 night min stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
30 night min stay
  • 5 BR,
  • 3 BA,
  • Sleeps 10
14 night min stay
16 more choices from the HomeAway Network
$4,300
per week
7 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 5
7 night min stay
(4)
$357 - $700
per night
1 - 7 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
1 - 7 night min stay
1 Review
$4,400 - $5,133
per week
3 - 7 night min stay
  • 3 BR,
  • 4 BA,
  • Sleeps 8
3 - 7 night min stay
1 Review
  • 3 BR,
  • Sleeps 4
7 night min stay
1 Review
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
2 Reviews
$2,002 - $4,004
per week
7 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
7 night min stay
(4)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night min stay
$300 - $329
per night
3 - 7 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 10
3 - 7 night min stay
(5)
$1,000
per night
7 - 13 night min stay
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
7 - 13 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 night min stay
$5,000 - $7,000
per week
7 - 14 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
7 - 14 night min stay
$5,000
per week
7 - 14 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 5
7 - 14 night min stay
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Recent Shelter Island Reviews

Perfect kid friendly getaway

5 of 5
We spent a week there last Summer with our two young children (4 and 1) and loved the house. Very spacious, with a nice playroom in the basement. The pool is gorgeous : big enough to swim and for children to have fun. It was spotless, well equipped (including for small children) and decorated with a lot of taste. With two small children we ended up spending a lot of time in and around the house and never got bored. The outside terrace and bbq are perfect for lunch and dinner by the pool. Also close to the beach, Sunset Beach (nice cocktails), Reddings (now Marie Effeil I think) for nice coffee, bread, cheese and viennoiseries. Mashomack Preserve nearby is gorgeous and they provide strollers for kids! You can also walk/jog to the beach from the house. Stefan and Sabrina are very nice, professional and responsive. All in all a perfect place to relax. So nice that we are planning to go back there this Summer with my sister and her family.
  • Submitted: Apr 24, 2015
  • Stayed: Sep 2014

LOVELY HOME - WONDERFUL LOCATION!

4 of 5
Lovely views of the harbor and very close to restaurants, cafes and shops - A great house and it was very comfortable for our 'girlfriends' weekend, we were five women who enjoyed relaxing on the front porch chatting with a glass of wine - We did cook one meal and it was great to have access to fresh herbs and tomatoes from the garden in the yard - The caretaker, Tom, even brought us peppers from his own garden that were delicious - Thank you Tom! This is a 5-star property but I gave it a 4-star rating only because of the constant traffic in front of the house going to the ferry - We were there in October so it was considerably less than it must be in the summer months - Even after saying that, I would definitely stay there again! (One suggestion would be to have a full length mirror somewhere in the bedroom area)
  • Submitted: Oct 29, 2014
  • Stayed: Oct 2014

Everything in the photos - and so much more!

5 of 5
This property is just absolutely stunning and so wonderful. My husband and I got married on Shelter Island and stayed here for 4 nights during our wedding weekend. We had countless numbers of family and friends filtering in and out throughout those days, and the size was more than accommodating. There are so many different spaces for different groups to socialize in, and we just had a blast. And nobody could get over what a beautiful property it was! It’s so well suited and fun for guests of any age, and every single room inside (there are many!), as well as the pool and the grounds outside are so well kept and spotless. And huge! Little touches like the amazing sound system, the on-site laundry services, all of the kitchen amenities, and the bikes in the garage just make you feel even more at home. And the beautiful porches both upstairs and downstairs are so perfect for relaxing. I enjoyed my coffee every morning on the upstairs balcony with a view of the water. The house is also on such a beautiful and quiet block only steps away from the beach, with the occasional deer families stopping by the front lawn. We just had the most fantastic and memorable few days on Shelter Island, and this house was integral to our good time. Andrew was also always so responsive and helpful in answering all of my questions both before our stay, and during. I can’t thank you enough for sharing your beautiful home with us Andrew! We will be back!
  • Submitted: Sep 29, 2014
  • Stayed: Sep 2014