Holiday rentals in Shelter Island Heights
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Top-rated holiday rentals in Shelter Island Heights
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Guest favourite
Guest house in Shelter Island
Lovely Island Cottage
Kick back and relax in this serene, stylish, sparkling adorable cottage. Large, airy living room with vaulted ceiling, fan, AC and full open kitchen. Cozy bedroom with queen size bed and luscious European linens. Spacious, bright bathroom with roomy stall shower. Newly painted with charming wicker furniture and cafe bistro table, Apple TV, Sonos and wifi. Enjoy the peace and beauty of Shelter Island living. Long time residents, we are happy to share all the ins and outs of the island.
16–23 NovIndividual Host,
€ 405 per night
4.95 out of 5 average rating, 22 reviews
Guest favourite
Apartment in Greenport
Beachside Waterview 2Br Condo w/ Pool in Greenport
Relax in a pristine 2Br condo with ocean & pool views. Our remodeled apartment is part of high-end development nestled on LI Sound, just minutes from downtown Greenport. Sip a glass of wine while watching sunset, catch some rays on the beach or deep in the pool.
2 bedroom condo with ocean view, beach, and pool (seasonal)
Comfortably sleeps 6
Private beach access year-around
Pool (seasonal)
Functional kitchenette
2 bathrooms, all toiletries
Linens and towels are provided
Smart TV
AC/Heat
22–29 MarIndividual Host,
€ 227 per night
4.91 out of 5 average rating, 107 reviews
Guest favourite
Flat in Greenport
Upscale Newly Constructed Apartment
Upscale 2- story building offers 3 bedrooms, 2 baths spacious apartment in the heart of Greenport. A vaulted ceiling in the great room (kitchen, dining & living room) with large windows and hardwood floors with plenty of natural light. Utilities included. CAC, Laundry. Less than a mile to a public beach, public transportation, restaurants, shops and Mitchell park. Off street parking for 2-3 cars.
It is a week minimum during the peak season ( memorial day weekend until labor day weekend)
8–15 JulIndividual Host,
€ 416 per night
4.95 out of 5 average rating, 122 reviews
Holiday rentals for every style
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Quick stats about holiday rentals in Shelter Island Heights
Total rentals | 290 properties |
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Rentals with a pool | 90 properties have a pool |
Pet-friendly rentals | 100 properties allow pets |
Family-friendly rentals | 210 properties are a good fit for families |
Total number of reviews | 8.5K reviews |
Nightly prices starting at | € 92 before taxes and fees |
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- Family-friendly rentals Shelter Island Heights
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