Guesthouse vacation rentals in The Hamptons
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Top-rated guesthouse rentals in The Hamptons
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 The Hamptons guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Westhampton
4.57 out of 5 average rating, 14 reviewsCharming Westhampton SandDollar Cottage. AC.
Guesthouse in Cherry Grove, Fire Island
4.92 out of 5 average rating, 76 reviewsOne Bedroom Cottage in Cherry Grove
Guesthouse in Montauk
4.74 out of 5 average rating, 58 reviewsWave Crest Oceanfront Cottage.
Guesthouse in Montauk
4.59 out of 5 average rating, 90 reviewsMontauk Heaven, Beach & Woods
Guesthouse in East Hampton
4.9 out of 5 average rating, 192 reviewsBeautiful Airy Barn in Springs
Guest house rentals with a patio
Guesthouse in Sag Harbor
5 out of 5 average rating, 3 reviewsSag Harbor Bungalow
Guesthouse in Montauk
4.71 out of 5 average rating, 14 reviewsStylish Surf Cottage Two Minute Walk From Beach
Guesthouse in Miller Place
4.7 out of 5 average rating, 46 reviewsPrivate guesthouse
Guesthouse in Hampton Bays
New place to stayPrivate Waterfront Cottage
Guesthouse in Sag Harbor
5 out of 5 average rating, 15 reviewsRomantic studio cottage; Walk to town
Guesthouse in Milford
New place to stayCute single floor cottage
Guesthouse in Shirley
4.96 out of 5 average rating, 72 reviewsLa casita J place
Guesthouse in Mastic Beach
5 out of 5 average rating, 4 reviewsCozy Guesthouse 10 min to Ocean
Guest house rentals with a washer and dryer
Guesthouse in Calverton
4.98 out of 5 average rating, 46 reviewsPrivate Luxe Cottage at Gates of Wine Country
Guesthouse in Shelter Island
4.89 out of 5 average rating, 9 reviewsStylish Studio Suite on Shelter Island
Guesthouse in Setauket- East Setauket
4.85 out of 5 average rating, 135 reviewsNewly Renovated Water Front Cottage in Setauket
Guesthouse in Hampton Bays
5 out of 5 average rating, 9 reviewsRetro Mid-Century Cottage 1/2 mile to CPI
Guesthouse in Southold
4.91 out of 5 average rating, 53 reviewsSouthold- Adorable 1 Bedroom Cottage
Guesthouse in Mount Sinai
4.56 out of 5 average rating, 39 reviewsGreat Outdoors Beach, Pool & Cozy Cabin Welcome!
Guesthouse in Shelter Island
5 out of 5 average rating, 64 reviewsBayfront 1BR/2BR detached guesthouse with pool
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