Vacation rentals with a patio in Greenport

Serene w/ large pool, 1 block to waterfront dining

Enjoy your private, chic Hamptons oasis! With large pool, located 1 block to waterfront dining. Swim in your pool, spark up the firepit, have a meal on the porch or under the stars! Cook in your Chef's kitchen + stream on your 80' TV. Enjoy the nature surrounding the home. Take a stroll 1 block to the best waterfront dining + cafe where you can enjoy your morning coffee overlooking the sea + have cocktails and dinner watching the sunset. You'll be 8 mins to Main St., shopping, beaches + more!

Beautiful 2 Bedroom, 2 Bath Greenport Village Loft

Enjoy this newly renovated 2 bedroom 2 bath loft apartment centrally located in the village of Greenport. Conveinient 5 minute walk to Front street, Main street shops, restaurants, bars and across from park/playground. Private rear deck for outdoor dining and a covered front porch for a glass of wine or morning coffee. Parking for 2 midsize cars in driveway. Power outlet available for EVs. Private yard with BBQ, firepit, adirondack chairs grassy area and lounges for sunning, reading or napping.

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

Year-Round Heated Pool Villa - 3 blocks from town

Pool heated to hot tub temperatures & open year round! This brand new construction house is perfect for large groups. Gather with friends and family in the double height ceiling open concept living room/dining room/kitchen area. Soak up the sun lounging by the pool. Take a super short walk to town to enjoy the incredible local shops, restaurants, and bars. Then end with a nightcap relaxing in the heated hot tub seating section of the pool. There's no better place to stay in Greenport Village.

Elegant Greenport Victorian-Winter Harbor House-

Winter Harbor House is a stylish Victorian walking distance from the best restaurants, bars and beaches in Greenport Village. Absolutely perfect location. Only a few hundred feet from the Mitchell Park/Marina, Waterfront Boardwalk/Beach and the North Ferry to Shelter Island. Enjoy gorgeous marina views and great people watching from the front porch. This 1890's Victorian has all the modern amenities you want while making you feel like you're experiencing a part of Greenport's history.

Greenport Village Getaway

Welcome to the Greenport Getaway! Located in the center of the Greenport Village, this spacious residential home boasts two recently renovated floors, a deck off the kitchen and private back yard. This home is walking distance to many restaurants in Greenport, and a short drive to the best vineyards and beaches the North Fork has to offer. This home is also walking distance from the Long Island Rail Road station, the ferry to Shelter Island, and the Hampton Jitney. We hope you enjoy!

Private 1st flr apt w/ patio 3 blocks from beach

We are centrally located in a quiet neighborhood within blocks from the heart of Greenport Village, Peconic Bay Beach, LIRR/Jitney, restaurants, shopping, Mitchell Park, and more! Explore local farms, wineries, breweries and all the North Fork has to offer. Beautifully furnished, ground floor apt with private entrance & patio area comfortably sleeps four, features a queen Tempur-Pedic mattress & convertible couch. Friendly, housetrained pets are welcome for an additional charge.

Greenport on The Golf Course - North Fork Rental

Golf, beaches, farms and vineyards! Magical views over Island's End Golf & Country Club from this updated 1800s farmhouse featuring 3 beds, 2.5 baths, and fenced yard. First floor has bathroom with stand up shower and bedroom. Attached 3 season breezeway game room with pool table and porch off kitchen. Outdoor patio area leading to expansive 1.17 acres with sweeping views over golf course. Located just 1 mile outside downtown Greenport! Experience the best of the North Fork!

The Bailey House

The Bailey House is a 1,900 square foot, fully renovated, 2 bed 2 bath home, with a modern rustic style. It has a beautiful indoor fireplace, baby grand piano, updated appliances, large smart tv and built in bluetooth speakers throughout. The backyard is fully fenced in with a pool, patio, fire pit, and koi pond. Just a short drive or long walk to town, the ferry, train, and jitney. This is not a new listing we have just changed management 😎

Modern Farmhouse Steps to Beach & Love Lane

Our home is professionally designed and set on a spacious, manicured green parcel enclosed by a Cul-de-sac with complete privacy inside and out. The home is designed with all modern conveniences and is located less than a 5 minute walk to Love Lane (Mattituck's charming downtown), Veteran's Beach (one of the best beaches on the Northfork) and the Mattituck train station. It is a place to relax, unwind and enjoy all that North Fork has to offer.

Walk to Breakwater Beach in Heart of Wine Country

Private and peaceful cottage walking distance to Breakwater Beach and Old Mill Inn Restaurant on the water opening Spring 2025. There are two large decks to relax by the firepit and drink your wine from the local wineries. Bikes, kayak, and paddle board are stored in the barn for guests use. Easy access to the marina, fishing, fine dining, vineyards, and farm stands.

Quaint Chalet w/Salt-heated Pool

Our heated pool is open until the beginning of October in 2025. A brand-new two-bedroom chalet that opens onto a heated, saltwater pool directly outside your patio doors. This is your ideal year-around gateway to experience Greenport. This private oasis is walking distance to Greenport Village, 4th & 5th Street beaches, as well as the train station and Jitney stop.