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Featured Guest Houses in Shelter Island

Estimated price for 1 night/2 adults

Bowen's by the Bays
Bowen's by the Bays
2.5 out of 5.0 177 West Montauk Highway, Hampton Bays, NY
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4.5/5 (55 reviews)

Love this place. I am running in the Southampton Marathon and this is perfect. The accommodations are wonderful. Clean, roomy and the kitchen is excellent for my very early breakfast. I will definitely come back and stay longer.

Reviewed on 28 Sep. 2019
Situated in Hampton Bays, this guesthouse is 2.7 mi (4.4 km) from Meschutt Beach and within 6 miles (10 km) of Ponquogue Beach and Shinnecock Hills Golf Course. ...
Victorian Seasons Stirling
Victorian Seasons Stirling
3.5 out of 5.0 857 NY-25, Greenport, NY
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Situated in Greenport, this beach guesthouse is within 1 mi (2 km) of Kontokosta Winery, Railroad Museum of Long Island and Island's End Golf and Country Club. ...
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Estimated price for 1 night/2 adults

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway, Montauk, NY
    4.0 out of 5.0
     
     
    4.3 out of 5 (300 reviews)

    Gurney's Montauk Resort & Seawater SpaAU$410

    23 Oct. - 24 Oct.

    Gurney's Montauk Resort & Seawater SpaAU$410
    Saybrook Point Inn, Marina and Spa

    Saybrook Point Inn, Marina and Spa

    2 Bridge St, Old Saybrook, CT
      3.5 out of 5.0
       
       
      4.7 out of 5 (241 reviews)

      Saybrook Point Inn, Marina and SpaAU$368

      30 Oct. - 31 Oct.

      Saybrook Point Inn, Marina and SpaAU$368

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