
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

Mod 8 / private bath & deck

Private Waterfront Cottage

Cozy Home

Guest House Southampton Village

Madison Bedroom B

The cleanest place you’ll see

A cozy bungalow in Southampton.

Steel & Modern House-
Guesthouses with a patio

Quaint One-Bedroom Cottage with Private Entry

Spacious cottage

Private guesthouse

2 BR Private Suite w/Private Living Room & Kitchen

Charming Pool House

The Private Guest House-Lake Ronkonkoma!

Retro Mid-Century Cottage 1/2 mile to CPI

Cozy Guesthouse 10 min to Ocean
Guest house rentals with a washing machine and dryer

Private Luxe Cottage at Gates of Wine Country

3 Bedroom Guest House in Southampton

Peaceful cottage

Southold- Adorable 1 Bedroom Cottage

Great Outdoors Beach, Pool & Cozy Cabin Welcome!

Charming 2 Bedroom 1 Bath Cottage w/ private yard

1 Bedroom Hamptons Waterfront Cottage Rental

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