Bed and breakfast vacation rentals in Southampton

Stunning Master Bed & Bath in Southampton Village Center

Luxury Experience! This beautiful master bed & bath has old-world charm in a timeless turn-of-the-century home. Relax and enjoy this stunning, spacious private suite. Enjoy the serenity of the back terrace or the charm of the front porch. Breakfast is served in the gorgeous kitchen every morning and can be enjoyed indoors or outside on the terrace. The house is just one block from Southampton Village Center & a mile from the ocean beaches. I have a total of four rooms each booked separately so you can come with friends or family! See all of my listings by clicking on my profile image. High vaulted ceiling, beautiful hardwood floors, comfortable bed, and ample closet space as well as sitting area. Access to entire master suite, living & dining room, kitchen, outside patio, and classic front porch, there is another patio area with a firepit. The house is set back on a flag lot and very private, only one block from Southampton Village Center and one mile from the ocean beaches. Walk from the LIRR train station (15 - 20 minutes), parking on premises available, local taxi's and Uber available. Continental Breakfast every morning, outdoor shower, bicycles available on a first come first serve basis.

1KING, Beaches, Kayaks, Wineries

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 & futon sleeper 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 the view 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.

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.

Head of Pond House - The Water Mill Room

Enjoy sweeping views of Mill Pond from this stylish room 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.

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.*

Southampton Center ~ Light & Airy Private Room

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 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 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!