Holiday rentals in Shelter Island
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Top-rated holiday rentals in Shelter Island
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Guest favourite
Guest suite in Hampton Bays
CHARMING OCEAN BUNGALOW
My ocean Bungalow is super well located in Hampton Bays. You will be 10 minutes away from the center of town where the Hampton Bays train station is. You also have Starbucks, Ride Aid, king Kullen, and great eateries at your fingertips. You will also have another two great supermarkets; Stop&Shop and Wild by Nature natural food store.
You will be staying in a room with a feeling of a Junior Suite with approximately 400sq feet, a much larger area than a standard room. It has an attached small full bathroom, a living space that I call “home theater” with a 75” smart TV, a wet Bar with Coffee, Expresso and Tea, your own refrigerator. No heavy cooking is allowed indoors but I will offer a grill outside, for the most gastronomically inclined guests ... there’s no dining area but you are more welcome to use the dining table at the outdoor stone patio.
One of the nicest thing about our location is that we are 5 minutes from Ponquogue Beach with excellent near by restaurants such as Oklands, Sundays on the Bay, on Beach Road and Dockers waterside on Dune Road. Meschutt beach is also a great location with live music throughout the summer, not a beach for surfers or adventure swimmers, since it’s on Peconic Bay, but on a plus side, there’s a full outdoor bar for adults, I love their Rum punch, and a full service snack bar, and a gift shop that sells beach gear... etc.
18–25 AprIndividual Host,
£106 per night
4.98 out of 5 average rating, 310 reviews
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.
18–25 AprIndividual Host,
£199 per night
4.88 out of 5 average rating, 308 reviews
Guest favourite
Flat 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!
7–14 SeptIndividual Host,
£249 per night
4.99 out of 5 average rating, 127 reviews
Holiday rentals for every style
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Quick stats about holiday rentals in Shelter Island
Total rentals | 140 properties |
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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 | £94 before taxes and fees |
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