
Guesthouse holiday 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.
Holiday 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 Westhampton
4.57 out of 5 average rating, 14 reviewsCharming Westhampton SandDollar Cottage. AC.

Guesthouse in Cherry Grove, Fire Island
4.92 out of 5 average rating, 76 reviewsOne Bedroom Cottage in Cherry Grove

Guesthouse in Montauk
4.74 out of 5 average rating, 58 reviewsWave Crest Oceanfront Cottage.

Guesthouse in East Hampton
4.9 out of 5 average rating, 195 reviewsBeautiful Airy Barn in Springs
Guesthouses with a patio

Guesthouse in Hampton Bays
4.87 out of 5 average rating, 60 reviewsQuaint One-Bedroom Cottage with Private Entry

Guesthouse in Montauk
4.71 out of 5 average rating, 14 reviewsStylish Surf Cottage Two Minute Walk From Beach

Guesthouse in Miller Place
4.71 out of 5 average rating, 49 reviewsPrivate guesthouse

Guesthouse in Bridgehampton
4.81 out of 5 average rating, 75 reviewsCentral Hamptons Guesthouse

Guesthouse in Fire Island Pines
5 out of 5 average rating, 16 reviews2 BR Private Suite w/Private Living Room & Kitchen

Guesthouse in Shirley
4.96 out of 5 average rating, 73 reviewsLa little house J place

Guesthouse in Mastic Beach
5 out of 5 average rating, 6 reviewsCozy Guesthouse 10 min to Ocean
Guest house rentals with a washing machine and dryer

Guesthouse in Calverton
4.98 out of 5 average rating, 46 reviewsPrivate Luxe Cottage at Gates of Wine Country

Guesthouse in Shelter Island
4.89 out of 5 average rating, 9 reviewsStylish Studio Suite on Shelter Island

Guesthouse in Setauket- East Setauket
4.85 out of 5 average rating, 135 reviewsNewly Renovated Water Front Cottage in Setauket

Guesthouse in Ronkonkoma
New place to stayPrivate Guest House-Lake Ronkonkoma

Guesthouse in Hampton Bays
5 out of 5 average rating, 9 reviewsRetro Mid-Century Cottage 1/2 mile to CPI

Guesthouse in Southold
4.91 out of 5 average rating, 54 reviewsSouthold- Adorable 1 Bedroom Cottage

Guesthouse in Mount Sinai
4.59 out of 5 average rating, 44 reviewsGreat Outdoors Beach, Pool & Cozy Cabin Welcome!
Destinations to explore
- Long Island Holiday rentals
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