Bed and breakfast holiday rentals in The Hamptons

White Contemporary in Classic Estate SOH for 2 max

***REQUESTS ONLY WITHIN 14 DAYS OF STAY. 3 NIGHT MINIMUM. 2GUESTS MAX stylish loft-like space in a gated estate , exquisite grounds and saltwater pool, close to ocean and Village shopping access by external staircase to a sunken patio . queen bed in an elevated area, CAC,full bathroom ,mini-frig..exclusive use of gym - Rogue ,rower, pingpong . Shared use of covered porches,lounging areas pool house for kitchenette (no cooking) 5.5% hotel/motel tax pay at check in

COMPLETE privacy ... and then some!

Welcome "New" & Returning Guests; our 2025 rooms are NOW open! MTK is an EXTRAordinary place; why not stay somewhere Special? This property is one of the most private in Montauk. The house offers complete seclusion for those that desire it. The house was built (new) in 2006/2007. This room is the Guest Master on the 2nd floor; it IS our BEST Guest Room. P.S. We DO have "Hot Water"; Airbnb, however, is having difficulty disclosing this fact.

Beautiful, Bright 3 room suite w/private entrance

Private entrance with front porch You will have 2 private bedrooms, 1.5 private bathrooms, and a large bright and cheerful private entrance room with a large couch and TV with Roku. Mini Fridge stocked with water, beer, milk, and sodas. Coffee maker, hot water kettle, microwave, toaster, coffee, tea, and breakfast cereal provided This suite is private and not shared with hosts 4 guests maximum, after 2 guests there is a $40 fee per additional guest per night

Peaceful Sag Harbor Geodesic Dome home

Convenient to all of the Hamptons, Sag Harbor has an amazing harbor, fabulous restaurants, cool mom-and-pop shops, and a quaint New England vibe. The most picturesque spot in the Hamptons, Sag Harbor is truly a gem. My house is a Buckminster Fuller-designed geodesic dome home. You'll be in a quiet cul-de-sac community 1 mile from Main Street with access to the back deck. Please check out all the photos to ensure my place is perfect for you.

1KING,Min to Beaches,KayaksPaddleboards,Wineries

Facing Shinnecock Bay, our Cottage King Rooms sleep two in a king bed dressed with soft plush sheets. From your deck overlooking the pool, sit and enjoy your coffee during the sunrise or unwind and relax at sunset. These rooms feature a standing shower bath to rinse off after your day at the beach or pool, smart TVs, mini fridge, coffee maker and handheld steamer upon request. Continental Breakfast everyday, 730am-930am in the Social Den.

Perfect in SH ~ Private Room Near Village Center

Bed & Breakfast Style ~ Old world charm in a turn of the century classic "Hamptons" house, one block from Southampton village and one mile from the beach. *Perfect place to work remotely with plenty of space and strong WIFI, ask about special weekday pricing for longer stays.* *I have a total of four rooms, each can be booked separately so you can come with friends or family! See all of my listings by clicking on my profile image.*

Grace House

Shelter Island Gem: Ranch on beautifully sited .53 acre abutting an 8 acre Reserve with a pond and open field. Wood fireplace. Lovely, verdant grounds w/brand new outdoor shower, covered porch overlooking the reserve. Launch your kayak or paddle board across the street. Minutes away wonderful restaurants and a short ferry ride to Sag Harbor or Greenport. A true country escape!

Head of Pond House- Edge of Woods Room

Stay in the center of the action in this one-of-a-kind place, our unique Bed & Breakfast located directly on Mill Pond in Water Mill. We are minutes away from all the Hamptons have to offer. Beaches, restaurants, museums and much more are all easily accessible from HOP House. En-suite room with Kingsize bed and lots of common areas will make your stay a memorable one.

Private Room in Amagansett Farmhouse

My house is in Amagansett 1 mile from the ocean beaches and 1 mile from the center of Amagansett Village. An easy bike ride to grocery stores, wine stores and all bars and restaurants in Amagansett village and East Hampton. We are a 5 minute walk to free public tennis, basketball and volleyball courts. An easy 15 minute car ride to Montauk.