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
Feb 11 – 18
Guesthouse in Shelter Island
4.97 out of 5 average rating, 105 reviewsWaterfront carriage house studio
Sep 20 – 27
Guesthouse in South Salem
4.93 out of 5 average rating, 220 reviews1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt
Mar 6 – 13
Guesthouse in Jamesport
4.97 out of 5 average rating, 107 reviewsWalk to Beautiful Beach in Heart of Wine Country
Jan 2 – 9
Guesthouse in Atlantic Highlands
4.87 out of 5 average rating, 303 reviewsPrivate cabin
Aug 23 – 30
Guesthouse in Warwick
4.96 out of 5 average rating, 249 reviewsBellvale Guest House on Solar Powered Mini-estate
Feb 27 – Mar 6
Guesthouse in Yonkers
4.76 out of 5 average rating, 105 reviewsSt James Guest House
Sep 24 – Oct 1
Guesthouse in Huntington Station
4.86 out of 5 average rating, 97 reviews2 large bedrooms in cozy little neighborhood.
Feb 27 – Mar 6
Guest house rentals with a patio
Guesthouse in Hempstead
4.86 out of 5 average rating, 80 reviewsPrivate Guest house with pool access.
Dec 24 – 31
Guesthouse in Shirley
4.97 out of 5 average rating, 35 reviewsLa casita J place
Sep 25 – Oct 2
Guesthouse in Massapequa
5.0 out of 5 average rating, 15 reviewsModern Custom Studio: 50 mins to NYC
Mar 25 – Apr 1
Guesthouse in Hampton Bays
4.91 out of 5 average rating, 43 reviewsQuaint One Bedroom Cottage with Private Entrance
Nov 30 – Dec 7
Guesthouse in Bridgehampton
4.82 out of 5 average rating, 61 reviewsCentral Hamptons Guesthouse
May 10 – 17
Guesthouse in Cedarhurst
5.0 out of 5 average rating, 25 reviewsCozy and Private Guest House Near JFK, LIRR, NYC!
Dec 10 – 17
Guesthouse in North Castle
4.98 out of 5 average rating, 43 reviewsMagical 1700's 1 bedroom cottage
Nov 30 – Dec 7
Guesthouse in Copiague
4.86 out of 5 average rating, 37 reviewsPalms by the bay: Waterside Cute Cozy Cottage
Jan 29 – Feb 5
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
Jul 29 – Aug 5
Guesthouse in Brewster
5.0 out of 5 average rating, 290 reviewsThe Cottage by the Lake: Hudson Valley Indulgence
Aug 1 – 8
Guesthouse in Bedford Hills
4.91 out of 5 average rating, 112 reviewsBarrett's Sanctuary
May 21 – 28
Guesthouse in Mamaroneck
4.94 out of 5 average rating, 127 reviewsYour Modern Guest Wing Near NYC
Aug 5 – 12
Guesthouse in Stonington
4.99 out of 5 average rating, 188 reviewsSuper Adorable Cottage + Fire pit + King Bed!
Oct 10 – 17
Guesthouse in Plainfield
4.91 out of 5 average rating, 251 reviewsCarriage House On Park (C.H.O.P.)
Jul 10 – 17
Guesthouse in Madison
5.0 out of 5 average rating, 58 reviewsThe Barn by the Sound
Mar 31 – Apr 7
Guesthouse in Southold
4.95 out of 5 average rating, 40 reviewsSouthold- Adorable 1 Bedroom Cottage
May 9 – 16
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