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 Cherry Grove, Fire Island
4.94 out of 5 average rating, 63 reviewsOne Bedroom Cottage in Cherry Grove
Guesthouse in Sag Harbor
4.89 out of 5 average rating, 99 reviewsCharming 2BR Cottage, Walk to Town
Guesthouse in Milford
4.92 out of 5 average rating, 193 reviewsSilversands Air-Bnb You’re right Here!
Guesthouse in East Hampton
4.9 out of 5 average rating, 189 reviewsBeautiful Airy Barn in Springs
Guesthouse in Montauk
4.74 out of 5 average rating, 58 reviewsWave Crest Oceanfront Cottage.
Guesthouse in Westhampton
4.33 out of 5 average rating, 9 reviewsCharming Westhampton SandDollar Cottage. AC.
Guest house rentals with a patio
Guesthouse in Shirley
4.95 out of 5 average rating, 41 reviewsLa casita J place
Guesthouse in Madison
4.96 out of 5 average rating, 73 reviewsBeachy & Bright Carriage House/5 min walk to Beach
Guesthouse in Madison
4.95 out of 5 average rating, 56 reviewsThe Rising Tide Cottage
Guesthouse in Hampton Bays
Hill Coast Cottage: Freshly Renovated
Guesthouse in Westhampton Beach
4.83 out of 5 average rating, 18 reviewsTennis & Sea Escape
Guesthouse in Bellport
5.0 out of 5 average rating, 10 reviewsGuest House retreat with amazing pool !!!
Guesthouse in Wading River
5.0 out of 5 average rating, 6 reviewsNorth Country Cottage
Guesthouse in West Haven
4.6 out of 5 average rating, 5 reviewsCozy Waterfront Oasis
Guest house rentals with a washer and dryer
Guesthouse in Southold
4.95 out of 5 average rating, 43 reviewsSouthold- Adorable 1 Bedroom Cottage
Guesthouse in Madison
5.0 out of 5 average rating, 60 reviewsThe Barn by the Sound
Guesthouse in Calverton
4.96 out of 5 average rating, 28 reviewsPrivate Luxe Cottage at Gates of Wine Country
Guesthouse in Hampton Bays
5.0 out of 5 average rating, 3 reviewsRetro Mid-Century Cottage 1/2 mile to CPI
Guesthouse in Guilford
5.0 out of 5 average rating, 63 reviewsPage Guest House
Guesthouse in Southold
Picture perfect 2 bedroom, 1 bath private cottage
Guesthouse in Clinton
4.94 out of 5 average rating, 195 reviewsThe Gardener's Cottage Dog friendly/ weekly/montly
Guesthouse in Setauket- East Setauket
4.85 out of 5 average rating, 135 reviewsNewly Renovated Water Front Cottage in Setauket
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- Family travel hub Tips and inspiration
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