Bed and breakfast holiday rentals in Suffolk County

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!

The Town View

What a rare treat to delight in a large and roomy space all to yourself in a quaint historical home. Be surrounded by five sunny windows that offer a panoramic view from so many different vantage points. The cozy nook with sofa bed, chairs, and desk with chair are perfect for sharing wine and cheese or to read a book. Slumber in the comfy queen sized bed and enjoy the bright bathroom with Jacuzzi tub and gentle rain shower that complete this guest room. This guest room is not pet friendly.

Vine + Sand Southold, NY's Newest B&B-Room 2

CHECK OUT OUR REDUCED 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.

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!

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

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.

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.

Relaxing Attic studio

Beautifully updated Colonial in Brooklawn section of Bridgeport offers an air bnb for individual or couple. Use of kitchen,laundry, pool, workout studio is available. Elegant walk-in shower with river rock stones and glass doors. Off-street parking available. I HAVE A CAT AND POODLE!! No guests' pet(s) allowed!