Holiday rentals with a washing machine and dryer in Greenport

Cozy Farmhouse Retreat in North Fork, NY

A 1905 farmhouse with modern touches, Arthur's Vineyard is a cozy 3-bed, 2-bath home in walking distance of Greenport village's beaches, marina, restaurants and boutiques. An open plan living area, breezy decor and a large landscaped backyard for spending relaxed summer days and nights with your family and friends, including the 4-legged ones. Walk to the train station/jitney or take a short drive to the wineries & farm stands of the North Fork. Recent updates: central heat/AC & new bathrooms.

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 Village View - Walk Downtown 2BR/1BA

Located in the heart of Greenport Village with easy walking access to restaurants, shops, Greenport Brewery, Kontakasta Winery, and much much more! Originally from Greenport, we look forward to hosting you and sharing our local favorites to make your stay memorable. Please note this rental may not suitable for small children due to the staircase. A new baby gate has been installed at the top of the stairs. Village of Greenport Short Term Rental Permit #R26-021.

Designer's Dream - Charming Boathouse

An architect's and interior decorator's dream home! This home is a historic boathouse built in the late 1890's with modern updates. In the middle of Greenport Village - walking distance to train station, Jitney stop, and Shelter Island Ferry as well as the best North Fork restaurants, vineyards, bars, and beaches. Two bedroom home with ground floor fireplace, outdoor shower (not enclosed), and beautifully landscaped outside patio w/grilling & dining areas.

Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)

100% Walking Score 1 block away from Village 3 blocks away from Beach. 1 block away from Shelter Island Ferry. Around the corner from Hampton Jitney & LIRR Newly renovated 2-Family Home! This is for rental of 1st floor apartment (only) plus cabana, plus outdoor jacuzzi. Close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place! Incredible location, safe, cozy.

Waterfront Escape | Private Beach, Pool & Views

Overlooking the Long Island Sound, this beautiful waterfront condo is the perfect North Fork coastal escape. Enjoy peaceful mornings with panoramic water views, spend your days soaking up the sun on the private beach, and unwind on the waterfront deck as the sun sets over the Sound. Located just minutes from Greenport Village, you’ll be close to charming boutiques, local farms, award-winning wineries, and gourmet dining.

1830 Historic garden wing - walk to it all

This historic Captain's house is located in the heart of beautiful Greenport Village. It dates back to 1830 and has been beautifully renovated preserving its historic detail. It has a huge garden with mature trees, plants and a wonderful gazebo. Once you step outside, you can walk to all the restaurants, bars, shops, the water as well as the Hampton Jitney and the LIRR. It's an ideal yet very quaint location.

Renovated Townhouse, Walk to All

Discover the North Fork from our stylishly renovated 100-year-old townhouse! Perfectly located, you can walk to town, beaches, and a local brewery. This bright, airy home features a new kitchen, central AC, and a private patio with a grill. Comfortably sleeping up to 8 guests, it's the ideal base for families or groups exploring Long Island's wine country. Park your car and enjoy a walkable getaway!

Upscale Newly Constructed Apartment

Upscale 2- story building offers 3 bedrooms, 2 baths spacious apartment in the heart of Greenport. A vaulted ceiling in the great room (kitchen, dining & living room) with large windows and hardwood floors with plenty of natural light. Utilities included. CAC, Laundry. Less than a mile to a public beach, public transportation, restaurants, shops and Mitchell park. Off street parking for 2-3 cars.

Lovely 2-bedroom apartment in a historic home

Restored apartment in a Victorian home, centrally located in the Village of Greenport. Short, few minutes walk to restaurants, shops, cafes in town. Also, conveniently located (10 minute walk) to the Hampton Jitney bus stop, LI Railroad and Shelter Island Ferry as well as local beaches. Enjoy the charm of a historic home, with all the convenience of modern amenities!

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.

Beach House in L.I. Wine Country

Time to wine 🍷 down and make your way to the scenic North Fork. A clean and clutter-free beach house awaits. The Navy House is centrally located in a quiet residential enclave, steps away from Norman E. Klipp Marine Park (aka Gull Pond Beach) and a short drive to Greenport’s Historic Village, vineyards and farmstands.