Vacation rentals with outdoor seating in Greenport

The Greenport Townhouse - Amazing Location & Large Backyard

The house is located on a .35 acre lot with plenty of outdoor dining space and a huge grass area with a firepit & hammock. There are 2 floors. The first floor has an open floor plan with a connecting kitchen, dining room, and living room. The kitchen is well equipped with a dish washer, electric stove/oven, refrigerator, and coffee bar. There is also a bedroom on the 1st floor with 2 full-sized beds. The 2nd floor has 3 bedrooms and a loft/den area. The three bedrooms on this floor have 1 queen bed+futon, 2 full-sized beds, and 2 twin beds (which can be made together to form a king upon request), respectively. All rooms have AC. There are 2 full bathrooms (1 on each floor) and a washer/dryer. Guests have access to the entire house and backyard area. We respect your privacy, but we are accessible if you have questions or need anything throughout your stay. Greenport was voted one of the prettiest towns in America by Forbes magazine. It has a vibrant and relaxing culture, offering access to beaches, wine tasting, and wonderful restaurants. The Shelter Island Ferry and Hampton Jitney stops are nearby. We are just a few short blocks from the Hampton Jitney stop, the LIRR station, and the Shelter Island Ferry. No car necessary - you can walk wherever you need!

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.

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!

Secluded Farmhouse - Studio Apartment Style Unit

Beautiful, quiet, studio apartment-style unit (private entrance w/full bath) tucked away in a modern farmhouse on a gorgeous, secluded North Fork farm. Guests have exclusive use of screen porch, fire pit, bbq and outdoor seating area. Jess is a private chef and yoga instructor, so be sure to inquire for services! Private hiking trails, fresh eggs, produce from garden, beach gear, Keurig, mini fridge, homemade granola, tea. Fresh eggs, seasonal veg from the garden, and meals (inquire!)

Updated apartment in historic village home

Quiet updated apartment close to Main St, boats and beaches. This second floor apartment has a private entrance and allows use of the front yard. Our home was built in 1880 but has just been renovated for a modern beach bungalow feel. The location is the perfect balance of a quiet neighborhood and close proximity to Marine Park, shops, restaurants, the Hampton Jitney and nightlife. The center of main street is less than a quarter mile from the apartment (4 minutes on foot). Walk to all!

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 Greenport Suite—private entry + near the beach

Welcome to The Greenport Suite! With its separate entrance, secluded outdoor patio space and ideal location, this newly-redesigned private suite in our contemporary Village home is perfect for enjoying a North Fork getaway. We are located just a few short blocks from bay beaches, the harbor, and public transport, while the area's celebrated wineries are a short drive or bike ride away. Come see why Forbes named Greenport one of the 11 prettiest villages in the United States!

Harbor Heights

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Comfortable Suite, a walk to the beach

Keep it simple at this spacious and peaceful home. Built in 2019, this home was specially designed for sustainable, green living; ground-source heating, and super insulation allow for minimal environmental impact. Less than five minute walk to McCabe’s Beach. Very near to wineries, farms, and the quaint shops and bakeries of Southold and Greenport. Little Fish restaurant and oyster sales all down the street. Short drive from Sparkling Pointe vineyard, and Love Lane.

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.

The Greenport Bungalow

Sweet Modern Bungalow Walking Distance to Town Located in the historic town of Greenport Village - 8 min walk to the beach, center of town, Shelter Island Ferry and LIRR... A newly built sun filled 3 bedroom house with all the amenities you would need when renting a home. Enjoy the large and fenced in back yard after a fun day in this historic Long Island fishing village. Great restaurants, and even better locally produced wine and beer!

Greenport Beach house Mini Resort Spa & Catering

Nestled steps from the beach, and all that Greenport and the North Fork has to offer, this exquisitely charming 3 bedroom 2 bathroom waterfront home is absolutely delightful.. You’ll love my place because of the views, the location, the people, the ambiance, the outdoors space, and the Saltwater pool.. My place is good for couples, solo adventurers, business travelers, families (with kids), groups, and furry friends (pets).