Bed and breakfast vacation rentals in Southampton

Vine + Sand Southold, NY's Newest B&B-Room 3

CHECK OUT OUR LOW SEASONAL RATES 50% OFF PEAK SEASON PRICES 6 WINERIES IN UNDER A MILE NO CLEANING FEES NO EXTRA PERSON FEES FREE BIKES FREE BEACH PASSES We're a genuine, licensed B&B. Experience this Insta-ready, newly renovated 1820 farmhouse. Your comfort and relaxation are our goal; designer flourishes are inside and out, filled with unique all-new furnishings. Our Salon features the latest in the arts: sculpture, painting, poetry, readings. Nothing has been overlooked.

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

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.*

Slice of heaven: Suite w/ separate entrance

Bellport village, a destination town overlooking the Great South Bay- as seen in Coastal Living ‘s top places to vacation. Written by Coastal Living: A gorgeously unassuming little seaport on Long Island’s South Shore, this village holds a royal flush of pleasures- a small town community feel, Colonial-style architecture, a charming marina, and even its own performing arts center, all just 90 minutes from New York City.

Sereno's Retreat

This room is named after the homestead's original owner, Sereno H. Scranton. Tucked away in the rear of the home, this a bright and sunny gem of a room with 4 big windows looking out on to the rear gardens. You also have the beautiful view of our giant Norway Spruce which is the tallest tree in Madison. This room offers a full sized bed and a private bathroom with shower. This guest room is not pet friendly.

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.