
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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for The Hamptons guesthouses
Family-Friendly guesthouses

One Bedroom Cottage in Cherry Grove

Beautiful Airy Barn in Springs

Montauk Heaven, Beach & Woods

Hamptons Private Studio Apartment

Waterfront cottage on beach
Guesthouses with a patio

The Guest House Retreat

Private guesthouse

The Private Guest House-Lake Ronkonkoma!

Retro Mid-Century Cottage 1/2 mile to CPI

La casita J place

Cozy Guesthouse 10 min to Ocean

Southampton Guesthouse Cottage

North Country Cottage
Guest house rentals with a washing machine and dryer

Private Luxe Cottage at Gates of Wine Country

3 Bedroom Guest House in Southampton

Cozy Hampton Bays Cottage for 5!

Stylish Studio Suite on Shelter Island

Southold- Adorable 1 Bedroom Cottage

Great Outdoors Beach, Pool & Cozy Cabin Welcome!

Charming 2 Bedroom 1 Bath Cottage w/ private yard

Hamptons Two Bedroom Cottage
Destinations to explore
- Long Island Holiday rentals
- Plainview Holiday rentals
- East River Holiday rentals
- New York Holiday rentals
- Hudson Valley Holiday rentals
- Boston Holiday rentals
- Jersey Shore Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Philadelphia Holiday rentals
- Ocean City Holiday rentals
- Washington Holiday rentals
- Rentals with beach access The Hamptons
- Rentals with an EV charger The Hamptons
- Rentals with outdoor seating The Hamptons
- Family-friendly rentals The Hamptons
- Rentals with lake access The Hamptons
- Waterfront rentals The Hamptons
- House rentals The Hamptons
- Rentals with a patio The Hamptons
- Bungalow rentals The Hamptons
- Luxury rentals The Hamptons
- Kid-friendly rentals The Hamptons
- Rentals with breakfast The Hamptons
- Rentals with an accessible height toilet The Hamptons
- Mansion rentals The Hamptons
- Villa rentals The Hamptons
- Rentals with a sauna The Hamptons
- Pet-friendly rentals The Hamptons
- Hotel rentals The Hamptons
- Beachfront rentals The Hamptons
- Farmstay rentals The Hamptons
- Condo rentals The Hamptons
- Rentals with a fireplace The Hamptons
- Apartment rentals The Hamptons
- Rentals with pools The Hamptons
- Cottage rentals The Hamptons
- Rentals with a hot tub The Hamptons
- Rentals with a fire pit The Hamptons
- Rentals with a washing machine and dryer The Hamptons
- Rentals with a kayak The Hamptons
- Beach house rentals The Hamptons
- Boutique hotel rentals The Hamptons
- Private suite rentals The Hamptons
- Fitness-friendly rentals The Hamptons
- Guesthouse rentals Suffolk County
- Guesthouse rentals New York
- Guesthouse rentals United States
- Cabins United States
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- Coastal Cottages United Kingdom
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- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Beach
- Charlestown Beach
- Fairfield Beach
- Yale University
- Southampton Beach
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Ocean Beach Park
- Napeague Beach
- Shinnecock Hills Golf Club
- Walnut Public Beach
- Woodmont Beach
- Jennings Beach
- Blue Shutters Beach
- Sunken Meadow State Park
- Amagansett Beach
- Ninigret Beach
- Silver Sands Beach
- Sandy Beach
- Groton Long Point Main Beach
- Brownstone Adventure Sports Park
- Cedar Beach
- Seaside Beach
- South Jamesport Beach