Bed and breakfast holiday rentals in The Hamptons

Vine + Sand Southold, NY's Newest B&B-Room 2

CHECK OUT OUR REDUCED 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.

White Contemporary in Classic Estate SOH for 3 max

***REQUESTS ONLY WITHIN 14 DAYS OF STAY. 3 person 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, twin in open space,CAC,full bathroom ,mini-frig..exclusive use of gym - Rogue ,rower . Shared use of porches, pool house for kitchenette (no cooking) 5.5% hotel/motel tax pay at check in No pets,smoking,vaping

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

Danny's Resort.2

bedroom with queen bed, sleeps 2 Situated on 3 acres at the end of a cul-de-sac, this home offers all the privacy, peace and quiet one could desire. Sag Harbor and Southampton Village are just minutes away. The Golden Pear in Southampton is 4.4 miles away. The Beacon restaurant in Sag Harbor is 5.9 miles away. The ferry to Shelter Island is 5 miles away. Includes continental breakfast, fresh ground coffee and bagels, oj, yogurt, berries ...

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.

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.*

Harbor Knoll Bed & Breakfast - Harbor Room

A historic Bed & Breakfast and Beachfront Inn in Greenport, NY. Experience the finest of seaside luxury at Harbor Knoll. Built in the Dutch Colonial style, and decorated in the English country house decor, Harbor Knoll is the ultimate romantic getaway. Each room is complete with wonderful views of the bay, beautiful furnishings, exquisite linens, and a selection of classic books. We'll show you the true meaning of hospitality.

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.

1BR,Mins to Beaches, Kayaks Paddleboards,Wineries

Welcome to Deluxe King Suite. This one bedroom sleeps 3 with a king & futon sleeper. Here, you can lounge in your sitting area while streaming on your Samsung TV. Prepare & enjoy meals in a full sit-in kitchen. Wash off from the beach in an oversized standing shower. Seasonal onsite kayak & paddleboard rentals available. Continental Breakfast is offered everyday, 830am-1030am in the Social Den.

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.