Guesthouse vacation rentals in The Hamptons
Find and book unique guesthouse rentals on Airbnb
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 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 Montauk
4.59 out of 5 average rating, 90 reviewsMontauk Heaven, Beach & Woods
Guesthouse in East Hampton
4.9 out of 5 average rating, 192 reviewsBeautiful Airy Barn in Springs
Guest house rentals with a patio
Guesthouse in Sag Harbor
5 out of 5 average rating, 3 reviewsSag Harbor Bungalow
Guesthouse in Montauk
4.71 out of 5 average rating, 14 reviewsStylish Surf Cottage Two Minute Walk From Beach
Guesthouse in Miller Place
4.69 out of 5 average rating, 45 reviewsPrivate guesthouse
Guesthouse in Hampton Bays
New place to stayPrivate Waterfront Cottage
Guesthouse in Sag Harbor
5 out of 5 average rating, 15 reviewsRomantic studio cottage; Walk to town
Guesthouse in Shirley
4.96 out of 5 average rating, 72 reviewsLa casita J place
Guesthouse in Mastic Beach
5 out of 5 average rating, 4 reviewsCozy Guesthouse 10 min to Ocean
Guest house rentals with a washer and dryer
Guesthouse in Calverton
4.98 out of 5 average rating, 46 reviewsPrivate Luxe Cottage at Gates of Wine Country
Guesthouse in Southampton
New place to stayPond-side Southampton Studio
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 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, 53 reviewsSouthold- Adorable 1 Bedroom Cottage
Guesthouse in Mount Sinai
4.56 out of 5 average rating, 39 reviewsGreat Outdoors Beach, Pool & Cozy Cabin Welcome!
Guesthouse in Shelter Island
5 out of 5 average rating, 64 reviewsBayfront 1BR/2BR detached guesthouse with pool
Destinations to explore
- New City Vacation rentals
- Long Island Vacation rentals
- Newark Vacation rentals
- Martha's Vineyard Vacation rentals
- Hoboken Vacation rentals
- Montauk Vacation rentals
- Washington Vacation rentals
- Philadelphia Vacation rentals
- New York Vacation rentals
- Jersey City Vacation rentals
- Boston Vacation rentals
- Cape Cod Vacation rentals
- Guesthouse rentals New York
- House rentals New York
- Guesthouse rentals United States
- House rentals United States
- House rentals Manhattan
- Villa rentals The Hamptons
- Beachfront rentals The Hamptons
- Cottage rentals The Hamptons
- Fitness-friendly rentals The Hamptons
- Rentals with pools The Hamptons
- Kid-friendly rentals The Hamptons
- Bed and breakfasts The Hamptons
- Private suite rentals The Hamptons
- Rentals with a kayak The Hamptons
- Luxury rentals The Hamptons
- Waterfront rentals The Hamptons
- Mansion rentals The Hamptons
- House rentals The Hamptons
- Rentals with a patio The Hamptons
- Condo rentals The Hamptons
- Boutique hotel rentals The Hamptons
- Rentals with a hot tub The Hamptons
- Rentals with beach access The Hamptons
- Rentals with an EV charger The Hamptons
- Bungalow rentals The Hamptons
- Rentals with a washer and dryer The Hamptons
- Rentals with outdoor seating The Hamptons
- Apartment rentals The Hamptons
- Rentals with lake access The Hamptons
- Rentals with a fireplace The Hamptons
- Rentals with breakfast The Hamptons
- Pet-friendly rentals The Hamptons
- Smoking-friendly rentals The Hamptons
- Family-friendly rentals The Hamptons
- Beach house rentals The Hamptons
- Monthly Rentals The Hamptons
- Farmstay rentals The Hamptons
- Rentals with a fire pit The Hamptons
- Guesthouse rentals Brooklyn
- House rentals Brooklyn
- House rentals New York
- Guesthouse rentals New York
- Guesthouse rentals Suffolk County
- House rentals Suffolk County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Things to do United States
- Sports activities United States
- Food and drink United States
- Art and culture United States
- Wellness United States
- Sightseeing United States
- Entertainment United States
- Nature and outdoors United States
- Things to do New York
- Art and culture New York
- Wellness New York
- Entertainment New York
- Sports activities New York
- Food and drink New York
- Sightseeing New York
- Nature and outdoors New York
- Things to do Suffolk County
- Things to do The Hamptons