Guesthouse holiday 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.
Holiday 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 Charlestown
4.89 out of 5 average rating, 271 reviewsCozy All Season Cabin Near Beach at Rockbriar Farm
Guesthouse in Fairfield
4.96 out of 5 average rating, 178 reviewsSouthport, CT across from BEACH
Guesthouse in Shelter Island
4.97 out of 5 average rating, 105 reviewsWaterfront carriage house studio
Guesthouse in South Salem
4.93 out of 5 average rating, 226 reviews1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt
Guesthouse in Groton
4.94 out of 5 average rating, 390 reviewsQuiet studio with sleeping loft and deck
Guesthouse in Huntington Station
4.85 out of 5 average rating, 102 reviews2 large bedrooms in cozy little neighborhood.
Guesthouse in Atlantic Highlands
4.87 out of 5 average rating, 307 reviewsPrivate cabin
Guesthouse in Warwick
4.97 out of 5 average rating, 258 reviewsBellvale Guest House on Solar Powered Mini-estate
Guesthouses with a patio
Guesthouse in Brewster
4.94 out of 5 average rating, 104 reviewsSherwood Barn - close to ski mountain
Guesthouse in Massapequa
4.9 out of 5 average rating, 20 reviewsModern Custom Studio: 50 mins to NYC
Guesthouse in Hempstead
4.85 out of 5 average rating, 87 reviewsPrivate Guest house with pool access.
Guesthouse in Shelter Island
5.0 out of 5 average rating, 51 reviewsBayfront 1BR/2BR detached guesthouse with pool
Guesthouse in Shirley
4.95 out of 5 average rating, 41 reviewsLa little house J place
Guesthouse in Hampton Bays
4.89 out of 5 average rating, 46 reviewsQuaint One Bedroom Cottage with Private Entrance
Guesthouse in Copiague
4.87 out of 5 average rating, 38 reviewsPalms by the bay: Waterside Cute Cozy Cottage
Guesthouse in Greenwich
4.94 out of 5 average rating, 65 reviewsThe Cottage in Greenwich
Guest house rentals with a washing machine and dryer
Guesthouse in Brookhaven
4.97 out of 5 average rating, 218 reviewsThe Unhampton
Guesthouse in Cold Spring
4.99 out of 5 average rating, 102 reviewsBright/modern forest escape. Near village & train
Guesthouse in Bedford Hills
4.91 out of 5 average rating, 115 reviewsBarrett's Sanctuary
Guesthouse in Mamaroneck
4.95 out of 5 average rating, 130 reviewsYour Modern Guest Wing Near NYC
Guesthouse in Stonington
4.99 out of 5 average rating, 193 reviewsSuper Adorable Cottage + Fire pit + King Bed!
Guesthouse in Hopkinton
4.96 out of 5 average rating, 108 reviewsCozy Vintage Cottage at Cornerstone Farm
Guesthouse in Plainfield
4.91 out of 5 average rating, 253 reviewsCarriage House On Park (C.H.O.P.)
Guesthouse in Madison
5.0 out of 5 average rating, 60 reviewsThe Barn by the Sound
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