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 9 – 16
Guesthouse in Milford
4.92 out of 5 average rating, 191 reviewsSilversands Air-Bnb You’re right Here!
Oct 24 – 31
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 27 – Oct 4
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
Oct 26 – Nov 2
Guesthouse in Shelter Island
5.0 out of 5 average rating, 50 reviewsBayfront 1BR/2BR detached guesthouse with pool
Sep 21 – 28
Guesthouse in Hampton Bays
5.0 out of 5 average rating, 3 reviewsRetro Mid-Century Cottage 1/2 mile to CPI
May 22 – 29
Guesthouse in Hampton Bays
Hill Coast Cottage: Freshly Renovated
Oct 25 – Nov 1
Guesthouse in Southold
Picture perfect 2 bedroom, 1 bath private cottage
Feb 25 – Mar 4
Guesthouse in Westhampton Beach
4.77 out of 5 average rating, 13 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
Apr 13 – 20
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 Southampton
4.88 out of 5 average rating, 42 reviewsModern Guesthouse
Jun 20 – 27
Guesthouse in Southold
4.95 out of 5 average rating, 40 reviewsSouthold- Adorable 1 Bedroom Cottage
Jun 12 – 19
Guesthouse in East Quogue
GuestHouse - Tennis court side luxury
May 2 – 9
Guesthouse in Setauket- East Setauket
4.85 out of 5 average rating, 135 reviewsNewly Renovated Water Front Cottage in Setauket
Mar 25 – Apr 1
Guesthouse in Hampton Bays
5.0 out of 5 average rating, 13 reviewsOne Bedroom Hamptons Waterfront Cottage
Oct 2 – 9
Guesthouse in Mount Sinai
4.6 out of 5 average rating, 5 reviewsGreat Outdoors Beach & Pool Welcome!
Oct 14 – 21
Guesthouse in East Quogue
4.91 out of 5 average rating, 22 reviewsHamptons Two Bedroom Cottage
Oct 17 – 24
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- Family travel hub Tips and inspiration
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