Holiday houses in North Bellport

Bellport Captain's Carriage House (2 Floors)

Built in 1876, The Captain’s Carriage House is a private two-story guest cottage in the heart of Bellport—central, yet your own oasis. Tucked behind hedges, this historic hideaway offers Village vibrancy + convenience just steps away. French doors open to a bright living/dining space where beach-chic style meets modern comfort with fast WiFi, Smart TV with Netflix, Bosch AC/heat, and a full kitchen. Plus, gas burning fireplace for fall stays. Upstairs, a King bedroom + en suite full bathroom.

Dream Beach Home w/ Heated Saltwater Pool: 4bd/2bt

Escape to this sanctuary nestled within the coveted Brookhaven Hamlet, offering an unparalleled summer experience. This stylish, newly-renovated home boasts 4 bedrooms plus 2 full bathrooms and kitchens, providing ample space for relaxation and rejuvenation. Gorgeous backyard with a huge deck, grill, heated pool, and new fire pit area. Walk a few minutes to the beach or head down the main road to a vibrant array of shops & restaurants in town. Unleash the true potential of your summer vacation!

South Shore Studio

Welcome to your private Mastic studio! This brand-new space is perfect for two adults looking for a quiet getaway. ​Inside, you'll find a queen-size bed, a full bathroom, and a small but fully equipped kitchen with everything you need to prepare meals. ​Step outside to your private outdoor space, featuring a fire pit and comfortable seating—perfect for relaxing after a day of exploring. ​Conveniently located, just a short drive from local shopping and all the best Long Island has to offer.

Charming 2 Bedroom apartment

Enjoy our charming 2 Bedroom apartment that is in a quiet and friendly neighborhood in a cul-de-sac. Private entrance on first floor of our house with 2 Bedrooms, 1 Bathroom, Living room, Dining area, and a Kitchen. Close to: Main highways (Sunrise HWY/Long Island Expressway), Grocery stores, Winery & Vineyards, Davis park ferry, Downtown Patchogue village (Restaurants, bars, breweries, shopping), Beaches, Top Golf, MacArthur airport, Long Island Community Hospital, St Joseph’s College.

Home away from Home!

Whether traveling for business or pleasure you will be close to everything when you stay at this centrally-located place. Many comforts of home Minutes from two major roadways, Sunrise Hwy and Long Island expressway. 3 minutes-Shopping Center. 3 minutes to Pickleball Heaven 11 minutes-Topgolf. 15 minutes- LI MacArthur Airport. 12 minutes-Patchogue Village-many restaurants and bars. Train Station-can take to NYC or Hampton/Montauk 20 minutes-Ocean-Smith Point Beach 30 mins-Hamptons

Chic Retreat: Hot Tub, Heated Pool, Sunroom

Escape the city at our newly renovated @BrookhavenChicRetreat Tucked in a quiet cul-de-sac w/ a fully fenced yard, this home is private and safe for families. Relax or entertain w two living areas thanks to our new sunroom. Summer: Private Pool, outdoor living space Year-Round: Outdoor Hot Tub Work: Fast Wi-Fi & desks in every room Laundry: Washer/dryer Minutes from Deer Run Farm, Post-Morrow Trails, and Bellport Village. The Hamptons are just 25 mins away. Book your coastal getaway!

Joyful Beach House, viewing The Great South Bay

Amazing Great South Bay view with access to Shorefront and Rider Parks. This Ranch has an unobstructed view of the Shorefront Band Shell. Watch concerts and sunsets from the comfort of your patio. Walk down to the Patchogue Beach Club and enjoy the pool and beach. This open-concept home has 2 bedrooms, one bath, a remodeled bathroom, and a kitchen. The kitchen has stainless steel appliances, a farm sink, and a butcher block countertop with natural lighting that will brighten the home.

Stunning Guest Suite in Medford

Welcome to our stunning two-bedroom suite on the first floor of our high ranch home. Enjoy a quiet, self-contained retreat where your comfort and privacy come first. The second floor is private and occupied by the host. Our home is close to local shops and transport. You can enter the suite through our calm backyard, creating a calm and welcoming atmosphere. PLEASE CHECK THE PHOTOS and HOUSE RULES BEFORE BOOKING to ensure the space meets your needs. Enjoy your stay!

*NEW* Reno Bellport Village Home + Saltwater Pool

This newly renovated 3-bedroom home features a chef's kitchen with an induction range and espresso machine. Heated floors are found throughout the kitchen and bathrooms. Outside, discover a fully fenced backyard with a new saltwater pool, deck sofas, and chaises. Please note: we open the pool from Memorial Day to Labor Day in the summer only. It is a saltwater pool, and they come to clean it each week on a Friday. It is heated, but it is not a hot tub.

Medford Seclusive Getaway

A weekend getaway at Medford Seclusive offers a perfect escape for relaxation and recreation. Imagine checking in and settling into your comfortable accommodations. Perhaps a room overlooking a plush garden or the sparkling pool. You’ll spend the weekend enjoying a variety of activities, like playing a game of ping pong or cornhole. Evenings might involve a fire side chat at the outdoor fire pit. You’ll check out feeling relaxed and rejuvenated.

Cozy Apartment with King Bed - Separate Entrance

Enjoy your stay in this private, clean and comfy environment. Space offers a bedroom with a king size bed and a desk for at-home work. Living room includes a smart TV and a sectional. Unleash your inner chef! Access to kitchen utensils, dinnerware, and pots/pans. Free parking on premises. Convenient location with many necessities nearby (mall/gas station/restaurants). Great for visiting family in Port Jefferson, Patchogue, etc!

Guest House retreat with amazing pool !!!

Slice of Heaven #2 Bellport Village, a destination town overlooking the great south bay as seen in Coatal 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, and even its own performing arts center, all 90mins from NYC.