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.

Head of Pond House - The Mill Pond Suite

Enjoy sweeping views of Mill Pond from this stylish suite at HOP House, our unique Bed & Breakfast in Water Mill. Large windows provide unobstructed lake and garden views, allowing you to relax in bed or an armchair while admiring the water and lush surroundings. The lake is a haven for wildlife; early risers often witness deer sipping from the shore and wild turkeys and geese roaming the underbrush. Besides the many wild birds you can occasionally see our residents eagles.

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.

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!

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.

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.