Guesthouse vacation rentals in Long Island
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Top-rated guesthouse rentals in Long Island
Guests agree: these guesthouse rentals 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 guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Charlestown
4.89 out of 5 average rating, 271 reviewsCozy All Season Cabin Near Beach at Rockbriar Farm
Guesthouse in Southampton
4.95 out of 5 average rating, 413 reviewsTiny Home in Prime Spot in Southampton Village
Guesthouse in Fairfield
4.96 out of 5 average rating, 178 reviewsSouthport, CT across from BEACH
Guesthouse in Huntington Station
4.85 out of 5 average rating, 103 reviews2 large bedrooms in cozy little neighborhood.
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 Jamesport
4.97 out of 5 average rating, 110 reviewsWalk to Beautiful Beach in Heart of Wine Country
Guesthouse in Shelter Island
4.97 out of 5 average rating, 105 reviewsWaterfront carriage house studio
Guesthouse in Groton
4.94 out of 5 average rating, 390 reviewsQuiet studio with sleeping loft and deck
Guest house rentals with a patio
Guesthouse in Brewster
4.93 out of 5 average rating, 105 reviewsSherwood Barn - close to ski mountain
Guesthouse in Massapequa
4.9 out of 5 average rating, 21 reviewsModern Custom Studio: 50 mins to NYC
Guesthouse in Hempstead
4.86 out of 5 average rating, 90 reviewsPrivate Guest house with pool access.
Guesthouse in Shirley
4.95 out of 5 average rating, 42 reviewsLa casita J place
Guesthouse in Hampton Bays
4.89 out of 5 average rating, 46 reviewsQuaint One Bedroom Cottage with Private Entrance
Guesthouse in Shelter Island
5 out of 5 average rating, 51 reviewsBayfront 1BR/2BR detached guesthouse with pool
Guesthouse in North Castle
4.98 out of 5 average rating, 49 reviewsMagical 1700's 1 bedroom cottage
Guesthouse in Southbury
4.96 out of 5 average rating, 55 reviewsThe Nest. Large studio in the Woods.
Guest house rentals with a washer and dryer
Guesthouse in Stonington
4.99 out of 5 average rating, 197 reviewsSuper Adorable Cottage + Fire pit + King Bed!
Guesthouse in Bedford Hills
4.91 out of 5 average rating, 116 reviewsBarrett's Sanctuary
Guesthouse in Cold Spring
4.99 out of 5 average rating, 102 reviewsBright/modern forest escape. Near village & train
Guesthouse in Mamaroneck
4.95 out of 5 average rating, 130 reviewsYour Modern Guest Wing Near NYC
Guesthouse in Hopkinton
4.96 out of 5 average rating, 109 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 Southold
4.95 out of 5 average rating, 43 reviewsSouthold- Adorable 1 Bedroom Cottage
Guesthouse in Huntington Station
4.99 out of 5 average rating, 68 reviewsModern fully updated 2nd Floor apartment
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