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 Fairfield
4.96 out of 5 average rating, 173 reviewsSouthport, CT across from BEACH
Mar 18 – 25
Guesthouse in Shelter Island
4.97 out of 5 average rating, 105 reviewsWaterfront carriage house studio
Jul 24 – 31
Guesthouse in South Salem
4.93 out of 5 average rating, 220 reviews1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt
Apr 18 – 25
Guesthouse in Jamesport
4.97 out of 5 average rating, 107 reviewsWalk to Beautiful Beach in Heart of Wine Country
Jan 26 – Feb 2
Guesthouse in Atlantic Highlands
4.88 out of 5 average rating, 304 reviewsPrivate cabin
Sep 17 – 24
Guesthouse in Warwick
4.96 out of 5 average rating, 249 reviewsBellvale Guest House on Solar Powered Mini-estate
Mar 9 – 16
Guesthouse in North Stonington
4.93 out of 5 average rating, 185 reviewsCharming Post and Beam cottage (near Foxwoods)
Jun 27 – Jul 4
Guesthouse in Yonkers
4.76 out of 5 average rating, 105 reviewsSt James Guest House
Mar 23 – 30
Guest house rentals with a patio
Guesthouse in Hempstead
4.86 out of 5 average rating, 80 reviewsPrivate Guest house with pool access.
Apr 9 – 16
Guesthouse in Massapequa
4.88 out of 5 average rating, 16 reviewsModern Custom Studio: 50 mins to NYC
Mar 11 – 18
Guesthouse in Shirley
4.97 out of 5 average rating, 35 reviewsLa casita J place
Sep 27 – Oct 4
Guesthouse in Calverton
4.96 out of 5 average rating, 28 reviewsPrivate Luxe Cottage at Gates of Wine Country
Apr 13 – 20
Guesthouse in Cedarhurst
5.0 out of 5 average rating, 25 reviewsCozy and Private Guest House Near JFK, LIRR, NYC!
Nov 15 – 22
Guesthouse in North Castle
4.98 out of 5 average rating, 43 reviewsMagical 1700's 1 bedroom cottage
Dec 28 – Jan 4
Guesthouse in Copiague
4.86 out of 5 average rating, 37 reviewsPalms by the bay: Waterside Cute Cozy Cottage
Sep 20 – 27
Guesthouse in Shelter Island
5.0 out of 5 average rating, 50 reviewsBayfront 1BR/2BR detached guesthouse with pool
Aug 10 – 17
Guest house rentals with a washer and dryer
Guesthouse in Stonington
4.97 out of 5 average rating, 223 reviewsTrue Artist Loft, 5 minutes to downtown Mystic
Sep 17 – 24
Guesthouse in Brewster
5.0 out of 5 average rating, 290 reviewsThe Cottage by the Lake: Hudson Valley Indulgence
Aug 1 – 8
Guesthouse in New Haven
4.94 out of 5 average rating, 241 reviewsSquare 6ix
Aug 29 – Sep 5
Guesthouse in Bedford Hills
4.91 out of 5 average rating, 112 reviewsBarrett's Sanctuary
Nov 7 – 14
Guesthouse in Mamaroneck
4.94 out of 5 average rating, 127 reviewsYour Modern Guest Wing Near NYC
May 23 – 30
Guesthouse in Stonington
4.99 out of 5 average rating, 188 reviewsSuper Adorable Cottage + Fire pit + King Bed!
Nov 26 – Dec 3
Guesthouse in Plainfield
4.91 out of 5 average rating, 251 reviewsCarriage House On Park (C.H.O.P.)
Jul 8 – 15
Guesthouse in Southold
4.95 out of 5 average rating, 40 reviewsSouthold- Adorable 1 Bedroom Cottage
May 9 – 16
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