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
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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 Milford
4.92 out of 5 average rating, 191 reviewsSilversands Air-Bnb You’re right Here!
Jan 14 – 21
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
Guesthouse in Sag Harbor
4.88 out of 5 average rating, 94 reviewsCharming 2BR Cottage, Walk to Town
Sep 18 – 25
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 Hampton Bays
5.0 out of 5 average rating, 3 reviewsRetro Mid-Century Cottage 1/2 mile to CPI
Jun 5 – 12
Guesthouse in Hampton Bays
Hill Coast Cottage: Freshly Renovated
Oct 26 – Nov 2
Guesthouse in Southold
Picture perfect 2 bedroom, 1 bath private cottage
Feb 26 – Mar 5
Guesthouse in Westhampton Beach
4.79 out of 5 average rating, 14 reviewsTennis & Sea Escape
Sep 15 – 22
Guesthouse in Bellport
5.0 out of 5 average rating, 9 reviewsGuest House retreat with amazing pool !!!
Oct 4 – 11
Guesthouse in Miller Place
4.69 out of 5 average rating, 32 reviewsPrivate guesthouse
Oct 20 – 27
Guest house rentals with a washer and dryer
Guesthouse in Southampton
4.8 out of 5 average rating, 10 reviewsSouthampton Village Getaway
May 13 – 20
Guesthouse in Southold
4.95 out of 5 average rating, 40 reviewsSouthold- Adorable 1 Bedroom Cottage
May 4 – 11
Guesthouse in Southampton
4.88 out of 5 average rating, 42 reviewsModern Guesthouse
Jun 20 – 27
Guesthouse in East Quogue
GuestHouse - Tennis court side luxury
May 22 – 29
Guesthouse in Setauket- East Setauket
4.85 out of 5 average rating, 135 reviewsNewly Renovated Water Front Cottage in Setauket
Apr 9 – 16
Guesthouse in Hampton Bays
5.0 out of 5 average rating, 13 reviewsOne Bedroom Hamptons Waterfront Cottage
Jan 17 – 24
Guesthouse in Mount Sinai
4.6 out of 5 average rating, 5 reviewsGreat Outdoors Beach & Pool Welcome!
Aug 31 – Sep 7
Guesthouse in East Quogue
4.91 out of 5 average rating, 22 reviewsHamptons Two Bedroom Cottage
Oct 17 – 24
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