Vacation rentals in Shelter Island
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Top-rated holiday rentals in Shelter Island
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Guest favourite
Guest suite in Sag Harbor
Artists Sag Harbor Village Retreat
January special -book second night for $125! This light and spacious Sag Harbor Village studio apartment is a 10 minute walk from historic Main St. 5 minutes to Village beach. French doors open onto outdoor sitting area.
Ideal for a fall or winter visit to explore the area during the quieter season. Main Street is lively and all restaurants are open. Central heat & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking. Fully self contained and private.
14 – 21 Nov
4.88 out of 5 average rating, 308 reviews
Guest favourite
Condo 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
1 – 8 Apr
4.91 out of 5 average rating, 107 reviews
Guest favourite
Apartment in Sag Harbor
Updated apartment in historic village home
Quiet updated apartment close to Main St, boats and beaches. This second floor apartment has a private entrance and allows use of the front yard. Our home was built in 1880 but has just been renovated for a modern beach bungalow feel. The location is the perfect balance of a quiet neighborhood and close proximity to Marine Park, shops, restaurants, the Hampton Jitney and nightlife. The center of main street is less than a quarter mile from the apartment (4 minutes on foot). Walk to all!
1 – 8 May
4.99 out of 5 average rating, 127 reviews
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Quick stats about holiday rentals in Shelter Island
Total rentals | 140 properties |
---|---|
Rentals with a pool | 50 properties have a pool |
Pet-friendly rentals | 50 properties allow pets |
Family-friendly rentals | 100 properties are a good fit for families |
Total number of reviews | 3K reviews |
Nightly prices starting at | $183 AUD before taxes and fees |
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