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 Cherry Grove, Fire Island
One Bedroom Cottage in Cherry Grove
Guesthouse in Sag Harbor
Charming 2BR Cottage, Walk to Town
Guesthouse in Milford
Silversands Air-Bnb You’re right Here!
Guesthouse in East Hampton
Beautiful Airy Barn in Springs
Guesthouse in Montauk
Wave Crest Oceanfront Cottage.
Guesthouse in Westhampton
Charming Westhampton SandDollar Cottage. AC.
Guesthouses with a patio
Guesthouse in Calverton
Private Luxe Cottage at Gates of Wine Country
Guesthouse in Hampton Bays
Retro Mid-Century Cottage 1/2 mile to CPI
Guesthouse in Madison
Beachy & Bright Carriage House/5 min walk to Beach
Guesthouse in Guilford
Page Guest House
Guesthouse in Madison
The Rising Tide Cottage
Guesthouse in Hampton Bays
Hill Coast Cottage: Freshly Renovated
Guesthouse in Southold
Picture perfect 2 bedroom, 1 bath private cottage
Guesthouse in Westhampton Beach
Tennis & Sea Escape
Guest house rentals with a washing machine and dryer
Guesthouse in Southampton
Modern Guesthouse
Guesthouse in Madison
The Barn by the Sound
Guesthouse in Southold
Southold- Adorable 1 Bedroom Cottage
Guesthouse in Southampton
Southampton Village Getaway
Guesthouse in East Quogue
GuestHouse - Tennis court side luxury
Guesthouse in Clinton
The Gardener's Cottage Dog friendly/ weekly/montly
Guesthouse in Setauket- East Setauket
Newly Renovated Water Front Cottage in Setauket
Guesthouse in Guilford
The Little Blue Cottage
Destinations to explore
- New City Holiday rentals
- Long Island Holiday rentals
- Newark Holiday rentals
- Martha's Vineyard Holiday rentals
- Montauk Holiday rentals
- Hoboken Holiday rentals
- New Haven Holiday rentals
- Washington Holiday rentals
- Philadelphia Holiday rentals
- New York Holiday rentals
- Jersey City Holiday rentals
- Boston Holiday rentals
- Guesthouse rentals New York
- House rentals New York
- Guesthouse rentals United States
- House rentals United States
- House rentals Manhattan
- Guesthouse rentals Manhattan
- Fitness-friendly rentals The Hamptons
- Rentals with a fireplace The Hamptons
- Monthly Rentals The Hamptons
- Beachfront rentals The Hamptons
- Cottage rentals The Hamptons
- Mansion rentals The Hamptons
- Rentals with a kayak The Hamptons
- Apartment rentals The Hamptons
- Rentals with lake access The Hamptons
- Beach house rentals The Hamptons
- Rentals with outdoor seating The Hamptons
- Rentals with pools The Hamptons
- Family-friendly rentals The Hamptons
- Luxury rentals The Hamptons
- Smoking-friendly rentals The Hamptons
- Villa rentals The Hamptons
- Farmstay rentals The Hamptons
- Rentals with a washing machine and dryer The Hamptons
- Rentals with a hot tub The Hamptons
- Pet-friendly rentals The Hamptons
- Condo rentals The Hamptons
- House rentals The Hamptons
- Rentals with a patio The Hamptons
- Waterfront rentals The Hamptons
- Bungalow rentals The Hamptons
- Bed and breakfasts The Hamptons
- Rentals with a sauna The Hamptons
- Kid-friendly rentals The Hamptons
- Rentals with beach access The Hamptons
- Rentals with an EV charger The Hamptons
- Rentals with breakfast The Hamptons
- Private suite rentals The Hamptons
- Rentals with a fire pit The Hamptons
- House rentals Brooklyn
- Guesthouse rentals Brooklyn
- Guesthouse rentals New York
- House 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