Holiday rentals with a patio in Greenport West

Serenity + privacy; 1 block to waterfront dining

Enjoy the privacy and serenity of your own home! Located near all of the best Hampton's attractions. Enjoy your large home surrounded by nature and calm vibes. Swim in your pool, spark up the BBQ + firepit, enjoy al fresco dining under the stars. Stream your 80' TV + cook in your large Chef's kitchen. Stroll just 1 block to the best waterfront dining + cafe for dinner/drinks/coffee on the sea. You will be 8 mins to Main St., 10 mins to beaches, close to museums, coffee shops + so much more!

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!

Delightful Cape House in Greenport

Delightful blue Cape with heated saltwater pool & hot tub nestled in the heart of Greenport on the North Fork. This lovely 4-bedroom, 2 full bath home is walking distance from the beach, shops, restaurants, Hampton Jitney, LIRR, and Ferry. Step into the enchanting backyard boasting heated saltwater pool, hot tub, outdoor shower & fire pit. The first floor includes 2 bedrooms, living room, eat-in kitchen, and a full bath, while the second floor has 2 additional bedrooms and another full bath

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.

Beautiful View Cottage

Welcome to "Belle Vue Cottage". This charming and inviting cottage is located in a quiet and peaceful neighborhood in the South Cove area of Old Saybrook. Spend your days relaxing at Harvey's Beach, perusing the shops and restaurants along Main Street, taking in a show at The Kate, and unwind at the end of the day in your backyard oasis equipped with an outdoor TV and fire pit. We are less than a mile from Saybrook Point Inn and Spa, and 10 minutes to Water's Edge Resort and Spa.

Stunning Farmhouse in NoFo I Heated Pool, Wineries

Modern Farmhouse Oasis | Private Pool | Near Hamptons & North Fork Escape to a stylish sanctuary where modern design meets pastoral charm. Set on a private, one-acre land, this farmhouse is a masterclass in coastal living. Enjoy sun-drenched lounge areas, a sparkling pool, and the constant, cooling luxury of Atlantic breezes. Inside, the home offers a seamless blend of contemporary interiors, and high-speed Wi-Fi—perfect for a peaceful retreat or a "work-from-anywhere" getaway.

Waterfront Greenport Condo

This two-bedroom, two-bathroom condo at Cliffside Resort offers a serene escape with breathtaking views of the Long Island Sound. Your stay includes access to Cliffside Resort’s fantastic amenities. Enjoy a heated swimming pool for relaxing swims, private beach access with lounge chairs for soaking up the sun, and a great lawn ideal for picnics, outdoor games, or a barbecue. Book your stay today and explore the vibrant attractions of Greenport and the North Fork!

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.

Newly renovated farmhouse - steps to Village

Luxury home on a quiet street in the Village of Greenport. This brand new Farmhouse has been fully renovated with all modern amenities - a quick walk to town and local vineyards! This gorgeous home is bright with sunshine and hard wood floors throughout. Effortless beachside living. Oversized private backyard is fully fenced in. Sleep comfortably in the brand new tempur-pedic beds throughout.

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.