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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.

Surf Scoter Cottage Shelter Island

New heated gunnite Pool & pea gravel driveway. 4BR renovated mid-century ranch with a breezy nautical theme. Central A/C. Giant back deck: Propane & Charcoal BBQ, Jacuzzi, Hammock & glorious Outdoor Shower. Private front & back yards. Fab mirrored bar, cozy kitchen, double-sink master bath+full 2nd bath. Impressive vinyl collect & 4 speaker Bluetooth stereo, Piano, chill basement media room + ping pong & foosball ! washer/dryer. 4 bikes, beach chairs, cooler & umbrella. $100 /dog sorry no cats

Beach Block Hideaway

100% Walking Score 4 blocks away from Village 1 block away from Beach. 4 blocks away from Shelter Island Ferry. 4 blocks from Hampton Jitney & LIRR Newly renovated home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops. Down block from beach restaurants and dining, the beach, nightlife, and public transport. Incredible location, safe, cozy. 2 King Size(Bedrooms) 2 Pull-out Full-size (Porch) 1 Couch (Living Room) 1 Bathroom

Waterfront NoFo Cottage w/ public beach access

Enjoy this waterfront cottage overlooking Marion Lake surrounded by lush landscape and wildlife. Experience the local Vineyards, take a leisurely stroll in downtown Greenport, ferry to Shelter Island, drive to Orient, or discover local hiking trails. Savor the culinary delights at the area's great restaurants, with fresh seafood and farm-to-table dining. Nestled between Greenport and Orient Point, East Marion provides access to all the North Fork has to offer. Rental Permit #1060

Artists Sag Harbor Village Retreat

This light and spacious Sag Harbor Village studio apartment is a 10 minute walk from historic Main St. 5 minutes to Village beach. French doors open onto outdoor sitting area. Fully self contained and private. Main Street is lively and all restaurants are open. Central heat with it’s own thermostat controls & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking in driveway close to entrance. Not suitable for infants or children.

Cozy Shelter Island 2 Bedroom 1 Bath Cottage

This cozy cottage is perfect place to relax and unwind. Located in the center of the island about a mile from the beach and nature preserve. Sleeps up to 9 people - with queen size aero bed provided. Linens, dishes, utensils etc. included. Fridge has icemaker and filtered water feature. Outdoor covered dining area with table and 8 chairs. 2 person swing, BBQ & outdoor shower. 2/3 acre property. Relax with the whole family at this peaceful place to stay.

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.

Freshly renovated farmhouse

Enjoy the modern feel in this completely remodeled 1900’s farmhouse. It is within walking distance (1 mile) to Greenport Village restaurants, shops, beaches, and transportation. Relax in the fenced in backyard while sitting around the fire pit, or the front porch drinking your morning coffee. It is the perfect place to get away! If you would like a shorter stay, please reach out.

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 Gem

Enjoy a stylish experience at this newly renovated centrally-located in the village of Greenport. Located only one block from Front Street and Main Street, you will be able to walk anywhere in downtown Greenport. Less than a 5 minute walk to the Shelter Island Ferry and LIRR. Parking for 2 cars. Queen sized air mattress and extra bedding are available.

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.

Private Suite in a Greenport Historical Townhouse

Enjoy the Greenport experience at this centrally located, renovated Victorian home. Our place is a few minutes walk into town, where there is a flourishing restaurant and food scene. Lots of shops, cafes to explore too and beaches are a 15 minute walk. Take a boat tour of the harbor from nearby Preston's Dock.