Vacation rentals with a patio in Greenport

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.

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)

Relax with friends / family at this home in a magical setting overlooking Lily pond Completely private but 5 mins to Sag Harbor downtown / restaurants / Havens beach, and 10 mins to Bridgehampton. Location, location! And Views! - 3 Beds and 2.5 baths + pool house - Pool house with twin sofa bed + full bath - 50ft heated Gunite pool (125/d extra to heat) - Outdoor deck overlooking pond - Amazing views! - Fire pit with Adirondack chairs Unique house to unwind while being close to the action

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!

Modern farmhouse w/ pool, beach, horses and winery

A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

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.

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 😎

The Village Villa 1st Floor

Welcome to the Village Villa—a newly renovated, spacious 3-bedroom home nestled right in the heart of Greenport Village. Located just 500 steps from a beloved local restaurant and grocery store, and a short walk to Front Street’s vibrant selection of coffee shops, breakfast cafés, award-winning restaurants, boutiques, bars, the Greenport Marina, and Mitchell Park—you’ll be perfectly positioned to enjoy everything the Village 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.

Secluded Farmhouse - Studio Apartment Style Unit

Private studio suite with separate entrance and full bath in a modern North Fork farmhouse on a peaceful farm property. Enjoy a screened porch, fire pit, and outdoor seating. Includes mini fridge, Keurig, tea, homemade granola, and seasonal eggs/produce. Attached to our home, so some light household noise is possible. Private chef + yoga services available.