Guesthouse vacation rentals in Long Island Sound
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Top-rated guesthouse rentals in Long Island Sound
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Long Island Sound guesthouse rentals
Family-friendly guest house rentals
Guesthouse in East Meadow
4.95 out of 5 average rating, 138 reviewsPetite Cottage
Oct 6 – 13
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 Charlestown
4.88 out of 5 average rating, 269 reviewsCozy All Season Cabin Near Beach at Rockbriar Farm
Mar 2 – 9
Guesthouse in Southampton
4.95 out of 5 average rating, 411 reviewsTiny Home in Prime Spot in Southampton Village
Oct 20 – 27
Guesthouse in Shelter Island
4.97 out of 5 average rating, 105 reviewsWaterfront carriage house studio
Jul 24 – 31
Guesthouse in Groton
4.94 out of 5 average rating, 385 reviewsQuiet studio with sleeping loft and deck
Oct 5 – 12
Guesthouse in Ulster Park
4.85 out of 5 average rating, 457 reviewsHudson Valley Hideaway
Mar 11 – 18
Guesthouse in Jamesport
4.97 out of 5 average rating, 107 reviewsWalk to Beautiful Beach in Heart of Wine Country
Jan 26 – Feb 2
Guest house rentals with a patio
Guesthouse in Gardiner
4.99 out of 5 average rating, 137 reviewsRed Barn Retreat - Shawangunk Mountains Getaway
Jun 12 – 19
Guesthouse in Montgomery
4.93 out of 5 average rating, 120 reviewsLuxury mins from angry orchard and city winery
Nov 15 – 22
Guesthouse in Calverton
4.96 out of 5 average rating, 28 reviewsPrivate Luxe Cottage at Gates of Wine Country
Apr 13 – 20
Guesthouse in Sharon
5.0 out of 5 average rating, 65 reviewsCottage with a Waterfall View
Sep 15 – 22
Guesthouse in Shirley
4.97 out of 5 average rating, 35 reviewsLa casita J place
Sep 27 – Oct 4
Guesthouse in Southbury
4.96 out of 5 average rating, 52 reviewsThe Nest. Large studio in the Woods.
Jul 21 – 28
Guesthouse in Madison
4.97 out of 5 average rating, 69 reviewsBeachy & Bright Carriage House/5 min walk to Beach
Dec 10 – 17
Guesthouse in North Castle
4.98 out of 5 average rating, 43 reviewsMagical 1700's 1 bedroom cottage
Dec 28 – Jan 4
Guest house rentals with a washer and dryer
Guesthouse in New Haven
4.94 out of 5 average rating, 241 reviewsSquare 6ix
Aug 29 – Sep 5
Guesthouse in Morristown
4.96 out of 5 average rating, 155 reviewsPrivate Guest House
Feb 9 – 16
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 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 New Milford
4.94 out of 5 average rating, 178 reviewsCharming Cottage w/Pastoral Views
Nov 7 – 14
Guesthouse in Stanfordville
4.92 out of 5 average rating, 164 reviewsEco Cottage in the Woods
Apr 1 – 8
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