Bed and breakfast holiday rentals in Southampton

1 King, Water Views, Beaches/Golf/Vineyard

Our studio king sleeps 3 & is perfect for small families or a group of friends that prefer the simplicity of their stay. These rooms are all dressed with soft plush sheets on one king bed & daybed situated in front of a coffee table to enjoy breakfast or play board games from the Social Den. Featuring either a shower/tub combo or a walk in shower to rinse off after your day at the beach or pool, mini fridge, handheld steamer upon request, & Samsung Smart TV. Enjoy water views from your deck.

Village ~ Summer Classic Southampton Private Room

Bright and Sunny! Get out of the city! Bed & Breakfast Style ~ Old world charm in a turn-of-the-century classic "Hamptons" house, one block from Southampton village & one mile from the beach. 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. Elegant, yet understated this house will feel like home. This is a private room with a full bed & shared bathroom. Ask about weekday discount

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.

Grace House

Shelter Island Gem: on beautifully sited .53 acre abutting an 8 acre Reserve with a pond and open field. Wood fplc and outdoor fire pit…verdant grounds w outdoor shower, covered porch overlooking the reserve. One 14-yr old 30-lb hypoallergenic dog LUCI and one outdoor cat Tootsie. Launch your kayak or paddle board acr the street. Stroll to wonderful restaurant “SALT” and a short ferry ride to Sag Harbor or Greenport. Price u see is for ONE King Bdrm . Second Queen Bedrm $175per nite

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.

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

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.

COMPLETE privacy ... and then some!

Welcome "New" & Returning Guests; our 2026 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 offer deals for longer stays; contact me.

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.

SEVEN on Shelter - Queen Guest Room

This newly restored award winning inn nails the 21st-century bed-and-breakfast formula, providing guests with a low-key hideaway while offering all the luxuries a modern globetrotter needs including sustainable toiletries (from Cold Spring Apothecary), walk-in well designed tile showers, flat-screen TVs and quality beds topped with goose-down comforters and colorful throw pillows from Capetown.