Guesthouse vacation rentals in Long Island
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Top-rated guesthouses in Long Island
Guests agree: these guesthouses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Long Island guesthouses
Family-friendly guesthouses
Guesthouse in Groton
4.94 out of 5 average rating, 387 reviewsQuiet studio with sleeping loft and deck
Guesthouse in Shelter Island
4.97 out of 5 average rating, 105 reviewsWaterfront carriage house studio
Guesthouse in Jamesport
4.97 out of 5 average rating, 107 reviewsWalk to Beautiful Beach in Heart of Wine Country
Guesthouse in South Salem
4.93 out of 5 average rating, 222 reviews1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt
Guesthouse in Atlantic Highlands
4.88 out of 5 average rating, 304 reviewsPrivate cabin
Guesthouse in Warwick
4.96 out of 5 average rating, 253 reviewsBellvale Guest House on Solar Powered Mini-estate
Guesthouse in North Stonington
4.93 out of 5 average rating, 185 reviewsCharming Post and Beam cottage (near Foxwoods)
Guesthouse in Yonkers
4.76 out of 5 average rating, 106 reviewsSt James Guest House
Guesthouses with a patio
Guesthouse in Brewster
4.94 out of 5 average rating, 101 reviewsSherwood Barn - close to ski mountain
Guesthouse in Massapequa
4.89 out of 5 average rating, 18 reviewsModern Custom Studio: 50 mins to NYC
Guesthouse in Hempstead
4.85 out of 5 average rating, 84 reviewsPrivate Guest house with pool access.
Guesthouse in Shirley
4.97 out of 5 average rating, 37 reviewsLa little house J place
Guesthouse in Shelter Island
5.0 out of 5 average rating, 50 reviewsBayfront 1BR/2BR detached guesthouse with pool
Guesthouse in Hampton Bays
4.91 out of 5 average rating, 44 reviewsQuaint One Bedroom Cottage with Private Entrance
Guesthouse in Bridgehampton
4.82 out of 5 average rating, 67 reviewsCentral Hamptons Guesthouse
Guesthouse in Greenwich
4.94 out of 5 average rating, 64 reviewsThe Cottage in Greenwich
Guesthouse rentals with a washer and dryer
Guesthouse in New Haven
4.94 out of 5 average rating, 243 reviewsSquare 6ix
Guesthouse in Stonington
4.99 out of 5 average rating, 191 reviewsSuper Adorable Cottage + Fire pit + King Bed!
Guesthouse in Bedford Hills
4.91 out of 5 average rating, 112 reviewsBarrett's Sanctuary
Guesthouse in Mamaroneck
4.95 out of 5 average rating, 128 reviewsYour Modern Guest Wing Near NYC
Guesthouse in Hopkinton
4.96 out of 5 average rating, 107 reviewsCozy Vintage Cottage at Cornerstone Farm
Guesthouse in Plainfield
4.91 out of 5 average rating, 251 reviewsCarriage House On Park (C.H.O.P.)
Guesthouse in Madison
5.0 out of 5 average rating, 59 reviewsThe Barn by the Sound
Guesthouse in Huntington Station
4.99 out of 5 average rating, 68 reviewsModern fully updated 2nd Floor apartment
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