Bed and breakfast holiday rentals in Southampton

Private Upstairs Chef’s Suite at Griswold Cottage

This is a Private suite with private bath. My place is close to the Village Green, it’s shops, restaurants, Chocolatier and bookstore. It’s a half mile to the Guilford beach, 4 miles to the Hammonasett beach in Madison. The house has great light, a cozy relaxing porch, a walking location to the village. You want to take a Picnic lunch with you? talk to me... My place is good for couples, solo adventurers, business travelers, bicyclists or hiking enthusiasts, anyone who just loves history!

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.

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.*

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.

Madison Getaway

This first floor deluxe room has a fireplace, private bath, large two person Jacuzzi, rain shower and queen size bed. The back window overlook the vista of the gardens, water fountain and gazebo. A cozy sun porch, and a large porch with wicker rockers to relax with lemonade, or wine as you watch the town go by the front view of the inn. This guest room is pet friendly.

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.