Bed and breakfast holiday rentals in Southampton

2BedKitchenette Water Views, Beaches/Golf/Vineyard

Our 2 full bed kitchenettes, Indigo & Ivory collection, are perfect for small families or a group of friends that prefer the extra amenities of being at home. Sleeping 4 on 2 full beds dressed with soft plush sheets. Rinse off after your day at the beach or pool in a shower/tub combo bath or a walk in shower. Kitchenette is equipped with counter height fridge, sink, Keurig, kettle & microwave. Catch the sunrise or sunset on your outside deck with water views. Southampton beach pass available!

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.

SEVEN on Shelter - Queen Room w/Private Bathroom

Seven is a number one rated resort style Inn on beautiful Shelter Island. One block from the beach, Seven features a heated swimming pool, and a gym. Each guest room has its own private bathroom. Our reviews are very good. Seven is walking distance to three restaurants, and Sunset Beach in the summer months - plus a nine hole public golf course & the Perlman Music Program. A European inspired breakfast buffet is offered each morning, including warm baguettes, croissants, yogurt, fruit

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

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.

Cottage King, Water Views, Beaches/Golf/Vineyard

Facing Shinnecock Bay, our Cottage King Rooms sleep two in a king bed dressed with soft plush sheets. From your deck overlooking the pool, sit and enjoy your coffee during the sunrise or unwind and relax at sunset. These rooms feature a standing shower bath to rinse off after your day at the beach or pool, smart TVs, mini fridge, coffee maker, tea kettle and handheld steamer upon request. Continental Breakfast everyday in the Social Den.

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.

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. Coffee maker, hot water kettle, microwave, toaster, coffee and tea 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

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.