Vacation rentals with a patio in Greenport

A well-lit bedroom features a spacious bed adorned with crisp white linens. Natural light enters through two windows, illuminating a rug beneath. A small table and a decorative plant are positioned beside the bed, creating a serene and inviting atmosphere.

4.96 out of 5 average rating, 49 reviews

Greenport Getaway - North Fork Rental

Vineyards, beaches, farms, golf, village of Greenport! Magical views over Island's End Golf & Country Club from this updated 1800s farmhouse featuring 3 beds, 2.5 baths, and fenced yard. First floor has bathroom with stand up shower and bedroom. Attached 3 season breezeway game room with pool table and porch off kitchen. Outdoor patio area leading to expansive 1.17 acres with sweeping views over golf course. Located just 1 mile outside downtown Greenport! Experience the best of the North Fork

A beachfront house with a wooden exterior is depicted, featuring multiple windows adorned with green planters. Soft sand covers the area in front, leading to the water, which reflects the clear blue sky. A small chair is visible on the sand, emphasizing the serene beach setting.

4.89 out of 5 average rating, 28 reviews

The Sandy Shack - Coastal Escape

Escape to your own private oasis at this charming beach house in Greenport. This beachfront home offers views of the ocean in every room. Inside, the living space gives plenty of natural light and sitting areas. The kitchen has everything you need to cook for family & friends. There are 4 beds to choose from, which can sleep 6 total. Outside, enjoy your own private beach as well as kayaks to use at your leisure. Located next to Greenport's best restaurants and wineries, book your stay today!

A serene screen porch features rustic wooden furniture, including a table and seating, with views of the expansive green yard. Light filters through large screens, creating a bright atmosphere. A walkway leads outdoors, while a dog is seen exploring the property.

4.98 out of 5 average rating, 178 reviews

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!)

4.92 out of 5 average rating, 115 reviews

A cozy living area features a comfortable gray sofa adorned with patterned pillows. A light-colored side table and an illuminated lamp create a soft glow. A decorative coffee table sits in front, accompanied by a potted plant in the corner, adding a touch of greenery.

Apartment in North Fork

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.

4.87 out of 5 average rating, 47 reviews

Cottage in Guilford

Your own Thimble Islands private cottage!

Escape to your own piece of private paradise! This unforgettable property encompasses 1+ acres of Narrows Island (Thimble Islands/Old Quarry Peninsula) - accessible by car via permanent land-bridge to island. Spectacular one-bedroom cottage with jaw-dropping surround oceanfront and accompanying views; modern and well-appointed. Approx 20 min to Yale, 5-10 min to town green and shops/restaurants. Indulge in sanctuary on an exclusive piece of Connecticut's most coveted shoreline.

Superhost

A bright living space features a classic sofa, two armchairs, and decorative lighting. A stone fireplace adds a cozy element, while a large window invites natural light. Indoor plants provide greenery, and a kitchen area with modern appliances is visible in the background.

Home in The Hamptons

4.85 out of 5 average rating, 126 reviews

Sag Harbor Wonder, 3 bedroom 2 Bath & Heated Pool

Situated on a half-acre of land, this classic shingle cottage with brand new designer interiors offers the ideal Hamptons getaway. Located in the picturesque village of Sag Harbor, less than a mile from town, bay beaches. 10 minute drive to Wolffer & ocean beaches. 3 bedrooms, 2 modern bathrooms and heated pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

4.92 out of 5 average rating, 50 reviews

An inviting two-story home is highlighted by a stone facade and a decorative chimney. A spacious deck is furnished with chairs for relaxation, surrounded by a well-kept lawn and a variety of trees, creating a serene outdoor environment.

Home in South End

Gorgeous home with saltwater pool. Steps to beach!

Built in 1928, this gorgeous home is fully equipped to host your getaway. You're within easy walking distance of Horton's Lighthouse, where lovely beach walks and stunning sunsets await you. The local wineries are all within short drives of this lovely retreat. Enjoy the new heated gunnite pool with plenty of poolside seating. The family friendly layout features plenty of seating inside and out. You're just 100 yards north of a public beach, come enjoy the sunsets!

A comfortable outdoor seating area features a sectional sofa adorned with colorful cushions. A sturdy rectangular coffee table made of stone sits at the center, surrounded by brick flooring. Large windows offer views of the water beyond.

5 out of 5 average rating, 14 reviews

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

★ "Beautiful hidden home on the water… enjoy the North Fork summer in style." Private beachfront property with 2 homes & views of Gardiner’s bay. ☞ Bikes + kayaks + paddle boards ☞ Wrap around balcony w/ seating ☞ Fully equipped + stocked kitchen ☞ Deck w/ lounging + water views ☞ Dedicated workspace + printer ☞ Master w/ king + bathroom ☞ 55” Smart TV + Xbox ☞ Indoor gas fireplace 6 mins → DT Greenport (cafes, dining, shopping) 13 mins → Orient Beach State Park ⛱

5 out of 5 average rating, 34 reviews

A vibrant sunset is captured over the Long Island Sound, with rich hues of orange and pink blending into the deep blue water. The shoreline is lined with lush greenery, while the sky is filled with soft, swirling clouds, creating a serene evening scene.

Apartment in North Fork

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!

Superhost

A modern black-clad home is visible with large windows reflecting soft light. Lounge chairs line the pool area, accompanied by umbrellas providing shade. A playful inflatable is positioned in the sparkling aqua pool, framed by lush greenery creating a serene outdoor environment.

Cottage in The Hamptons

4.75 out of 5 average rating, 102 reviews

Spacious East Hampton Getaway with Pool

This bright and comfortable 3 bedroom, 2 bath Scandinavian home awaits! Located just a 5 minute drive Sag Harbor and 10 minutes to the heart of East Hampton to enjoy beaches, shopping, restaurants and bars. The light hardwood floors create a crisp feel that you have to witness. The first floor's two guest beds open out to a lovely eat-in kitchen with dining and living rooms featuring a wood-burning fireplace and pool to check every box for year-round fun.

A bright living area features light-colored walls and wooden flooring. A comfortable sofa and a plush chair are arranged around a rustic coffee table. A ceiling fan hangs above, while a kitchen with a blue island is visible in the background, enhancing the space's openness.

4.93 out of 5 average rating, 145 reviews

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.