Guest house holiday rentals in The Hamptons
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Top-rated guest house rentals in The Hamptons
Guests agree: these guest house rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for guest house rentals in The Hamptons
Family-friendly guest house rentals
Guest house in Cherry Grove, Fire Island
4.94 out of 5 average rating, 63 reviewsOne Bedroom Cottage in Cherry Grove
Guest house in Sag Harbor
4.89 out of 5 average rating, 98 reviewsCharming 2BR Cottage, Walk to Town
Guest house in Milford
4.92 out of 5 average rating, 192 reviewsSilversands Air-Bnb You’re right Here!
Guest house in East Hampton
4.9 out of 5 average rating, 189 reviewsBeautiful Airy Barn in Springs
Guest house in Montauk
4.74 out of 5 average rating, 58 reviewsWave Crest Oceanfront Cottage.
Guest house in Westhampton
4.33 out of 5 average rating, 9 reviewsCharming Westhampton SandDollar Cottage. AC.
Guest house rentals with a patio
Guest house in Shirley
4.97 out of 5 average rating, 39 reviewsLa little house J place
Guest house in Madison
4.97 out of 5 average rating, 70 reviewsBeachy & Bright Carriage House/5 min walk to Beach
Guest house in Madison
4.95 out of 5 average rating, 56 reviewsThe Rising Tide Cottage
Guest house in Hampton Bays
Hill Coast Cottage: Freshly Renovated
Guest house in Westhampton Beach
4.81 out of 5 average rating, 16 reviewsTennis & Sea Escape
Guest house in Bellport
5.0 out of 5 average rating, 9 reviewsGuest House retreat with amazing pool !!!
Guest house in Wading River
5.0 out of 5 average rating, 4 reviewsNorth Country Cottage
Guest house in West Haven
4.5 out of 5 average rating, 4 reviewsCozy Waterfront Oasis
Guest house rentals with a washing machine and dryer
Guest house in Southold
4.95 out of 5 average rating, 41 reviewsSouthold- Adorable 1 Bedroom Cottage
Guest house in Southampton
4.89 out of 5 average rating, 46 reviewsModern Guesthouse
Guest house in Madison
5.0 out of 5 average rating, 60 reviewsThe Barn by the Sound
Guest house in Hampton Bays
5.0 out of 5 average rating, 3 reviewsRetro Mid-Century Cottage 1/2 mile to CPI
Guest house in Calverton
4.96 out of 5 average rating, 28 reviewsPrivate Luxe Cottage at Gates of Wine Country
Guest house in Guilford
5.0 out of 5 average rating, 62 reviewsPage Guest House
Guest house in East Quogue
GuestHouse - Tennis court side luxury
Guest house in Southold
Picture perfect 2 bedroom, 1 bath private cottage
Destinations to explore
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