Guesthouse vacation rentals in The Hamptons
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouses in The Hamptons
Guests agree: these guesthouses 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 guesthouses
Family-friendly guesthouses
Guesthouse in Cherry Grove, Fire Island
4.93 out of 5 average rating, 61 reviewsOne Bedroom Cottage in Cherry Grove
Guesthouse in Milford
4.92 out of 5 average rating, 192 reviewsSilversands Air-Bnb You’re right Here!
Guesthouse in East Hampton
4.9 out of 5 average rating, 187 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.
Guesthouse in Sag Harbor
4.89 out of 5 average rating, 96 reviewsCharming 2BR Cottage, Walk to Town
Guesthouses with a patio
Guesthouse in Shirley
4.97 out of 5 average rating, 37 reviewsLa little house J place
Guesthouse in Hampton Bays
Hill Coast Cottage: Freshly Renovated
Guesthouse in Westhampton Beach
4.8 out of 5 average rating, 15 reviewsTennis & Sea Escape
Guesthouse in Southampton
5.0 out of 5 average rating, 7 reviewsSummer rental- July-August cute home
Guesthouse in Bellport
5.0 out of 5 average rating, 9 reviewsGuest House retreat with amazing pool !!!
Guesthouse in Miller Place
4.69 out of 5 average rating, 32 reviewsPrivate guesthouse
Guesthouse in Montauk
4.71 out of 5 average rating, 14 reviewsStylish Surf Cottage Two Minute Walk From Beach
Guesthouse in Fire Island Pines
5.0 out of 5 average rating, 4 reviews2 BR Private Poolside Suite in Fire Island Pines
Guesthouse rentals with a washer and dryer
Guesthouse in Shelter Island
5.0 out of 5 average rating, 50 reviewsBayfront 1BR/2BR detached guesthouse with pool
Guesthouse in Southampton
4.8 out of 5 average rating, 10 reviewsSouthampton Village Getaway
Guesthouse in Southampton
4.89 out of 5 average rating, 44 reviewsModern Guesthouse
Guesthouse in Southold
4.95 out of 5 average rating, 41 reviewsSouthold- Adorable 1 Bedroom Cottage
Guesthouse in Hampton Bays
5.0 out of 5 average rating, 3 reviewsRetro Mid-Century Cottage 1/2 mile to CPI
Guesthouse in Calverton
4.96 out of 5 average rating, 28 reviewsPrivate Luxe Cottage at Gates of Wine Country
Guesthouse in East Quogue
GuestHouse - Tennis court side luxury
Guesthouse in Southold
Picture perfect 2 bedroom, 1 bath private cottage
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