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
Get the amount of space that is right for you
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
Mar 2 – 9
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 11 – 18
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 Shelter Island
4.97 out of 5 average rating, 105 reviewsWaterfront carriage house studio
Jul 28 – Aug 4
Guesthouse in Groton
4.94 out of 5 average rating, 385 reviewsQuiet studio with sleeping loft and deck
Sep 27 – Oct 4
Guesthouse in Ulster Park
4.85 out of 5 average rating, 457 reviewsHudson Valley Hideaway
Jan 9 – 16
Guesthouse in Jamesport
4.97 out of 5 average rating, 107 reviewsWalk to Beautiful Beach in Heart of Wine Country
Nov 4 – 11
Guesthouse in New Paltz
4.99 out of 5 average rating, 387 reviewsRidge View Walk-Up | Your GUNKS Home
Jun 11 – 18
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 Sharon
5.0 out of 5 average rating, 65 reviewsCottage with a Waterfall View
Aug 21 – 28
Guesthouse in Calverton
4.96 out of 5 average rating, 28 reviewsPrivate Luxe Cottage at Gates of Wine Country
Apr 14 – 21
Guesthouse in Shirley
4.97 out of 5 average rating, 35 reviewsLa casita J place
Jan 9 – 16
Guesthouse in North Castle
4.98 out of 5 average rating, 44 reviewsMagical 1700's 1 bedroom cottage
Oct 11 – 18
Guesthouse in Southbury
4.96 out of 5 average rating, 52 reviewsThe Nest. Large studio in the Woods.
Feb 26 – Mar 5
Guesthouse in Madison
4.97 out of 5 average rating, 69 reviewsBeachy & Bright Carriage House/5 min walk to Beach
Nov 29 – Dec 6
Guest house rentals with a washer and dryer
Guesthouse in New Haven
4.94 out of 5 average rating, 241 reviewsSquare 6ix
Aug 27 – Sep 3
Guesthouse in Cranston
4.92 out of 5 average rating, 302 reviewsWaterfront Studio, 10 min to Downtown Providence
Oct 12 – 19
Guesthouse in Morristown
4.96 out of 5 average rating, 155 reviewsPrivate Guest House
Dec 30 – Jan 6
Guesthouse in Stonington
4.97 out of 5 average rating, 223 reviewsTrue Artist Loft, 5 minutes to downtown Mystic
Oct 20 – 27
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
Sep 23 – 30
Guesthouse in Mamaroneck
4.94 out of 5 average rating, 127 reviewsYour Modern Guest Wing Near NYC
Aug 11 – 18
Guesthouse in Stonington
4.99 out of 5 average rating, 188 reviewsSuper Adorable Cottage + Fire pit + King Bed!
Nov 26 – Dec 3
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