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
4.93 out of 5 average rating, 61 reviewsOne Bedroom Cottage in Cherry Grove
Sep 13 – 20
Guesthouse in Sag Harbor
4.88 out of 5 average rating, 94 reviewsCharming 2BR Cottage, Walk to Town
Apr 24 – May 1
Guesthouse in Milford
4.92 out of 5 average rating, 191 reviewsSilversands Air-Bnb You’re right Here!
Sep 25 – Oct 2
Guesthouse in East Hampton
4.9 out of 5 average rating, 187 reviewsBeautiful Airy Barn in Springs
Oct 11 – 18
Guesthouse in Westhampton
4.33 out of 5 average rating, 9 reviewsCharming Westhampton SandDollar Cottage. AC.
Sep 28 – Oct 5
Guest house rentals with a patio
Guesthouse in Shirley
4.97 out of 5 average rating, 34 reviewsLa casita J place
May 13 – 20
Guesthouse in Shelter Island
5.0 out of 5 average rating, 50 reviewsBayfront 1BR/2BR detached guesthouse with pool
Jul 13 – 20
Guesthouse in Madison
4.97 out of 5 average rating, 68 reviewsBeachy & Bright Carriage House/5 min walk to Beach
Nov 16 – 23
Guesthouse in Hampton Bays
5.0 out of 5 average rating, 3 reviewsRetro Mid-Century Cottage 1/2 mile to CPI
Jun 5 – 12
Guesthouse in Guilford
5.0 out of 5 average rating, 61 reviewsPage Guest House
Sep 13 – 20
Guesthouse in Madison
4.95 out of 5 average rating, 56 reviewsThe Rising Tide Cottage
Aug 5 – 12
Guesthouse in Hampton Bays
Hill Coast Cottage: Freshly Renovated
Dec 3 – 10
Guesthouse in Southold
Picture perfect 2 bedroom, 1 bath private cottage
Feb 26 – Mar 5
Guest house rentals with a washer and dryer
Guesthouse in Madison
5.0 out of 5 average rating, 58 reviewsThe Barn by the Sound
Jan 28 – Feb 4
Guesthouse in Southold
4.95 out of 5 average rating, 40 reviewsSouthold- Adorable 1 Bedroom Cottage
May 7 – 14
Guesthouse in Southampton
4.88 out of 5 average rating, 42 reviewsModern Guesthouse
May 9 – 16
Guesthouse in Southampton
4.8 out of 5 average rating, 10 reviewsSouthampton Village Getaway
May 17 – 24
Guesthouse in East Haven
4.94 out of 5 average rating, 31 reviewsAdorable private 1-bedroom guesthouse with parking
Jun 8 – 15
Guesthouse in East Quogue
GuestHouse - Tennis court side luxury
May 19 – 26
Guesthouse in Clinton
4.94 out of 5 average rating, 192 reviewsThe Gardener's Cottage Dog friendly/ weekly/montly
Oct 24 – 31
Guesthouse in Setauket- East Setauket
4.85 out of 5 average rating, 135 reviewsNewly Renovated Water Front Cottage in Setauket
Mar 11 – 18
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