
Cottage holiday rentals in Greenport
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Top-rated cottage rentals in Greenport
Guests agree: these cottages are highly rated for location, cleanliness and more.

Modern Southampton Cottage | Heated Pool & Peloton
Modern Hamptons cottage with mid-century modern interior, our 3 bedroom/ 2 bathroom cottage is set on manicured grounds and perfectly equipped for your stay. Heated gunite pool (summer months only) with retractable cover, Peloton bike and Central Air throughout. Newly renovated kitchen with high end appliances, large outdoor deck perfect for entertaining with new Weber grill. Private driveway accommodates 4 cars. 4 adult bicycles. 8 min ride to Southampton village. 15 min to Coopers Beach.

Savor Ocean Sunsets at a Soothing Beachfront Haven
Newly renovated and featured as a top Airbnb by New York Magazine, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

Enchanted Cottage on the Marsh, walk to beach
Enjoy an idyllic stay at Enchanted Cottage on the Marsh! Private, quiet one bedroom cottage on Farm River with breathtaking views from deck. Take in the herons, ospreys and other birds among the natural surroundings while relaxing on your very private deck. Or take a stroll to the neighborhood beach, trails or a restaurant. Enjoy daily retreat from everyday life. We want you to have a relaxing stay with us, free from worry. 10 min walk to beach, trails, 10 min drive to Yale University.

Cozy Home In Short Beach Community
A cozy home in a beach community that has a central location with easy access to outdoor activities & local restaurants. The home is also 5 minutes from the Branford Train Station, Stony Creek Brewery, & Branford's town center. We are also a 10 minute drive from New Haven, home to Yale University, Yale Hospital and other colleges/universities. Our guests also gain access to Johnsons' Beach, a private residents only beach, located just around the corner from the home(4min walk/900ft)

Waterfront Joshua Cove Cottage with private beach.
Beautiful architecturally designed 1 Bedroom + loft Cottage on Joshua Cove in Guilford. The sunsets are spectacular from your own private beach. Enjoy Fall Foliage, swimming, fishing, and some of the best Kayaking from this perfect setting. Minutes from the Guilford train station, restaurants, shopping, and historic town green. The property is just 15 minutes from New Haven, and the Yale campus. The Thimble Island cruise, and the Ct. river steam train/cruise are nearby as well.

Charming Southampton Light filled Cottage
Escape and relax in this beautiful tranquil Southampton retreat! Newly remodeled cottage just blocks from the water. The home is nestled on 1/2acre quiet park-like setting located at the end of a long gravel driveway. Enjoy the private outdoor space with a fire pit, outdoor dining table, new dual BBQ and lounge chairs. Inside, the large dining room table easily sits 8. This stylish Coastal farmhouse has all new beds and furniture. Complete with Wifi, Cable, AC and Nespresso maker!

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.

The Cottage at Indian Cove
A charming original turn of the century cottage that was recently renovated. One main room plus a full bathroom and Ikea kitchen. It includes a back porch that gets a perfect amount of late afternoon sun. The cottage has electric baseboard heat for cool nights. We are located in Indian Cove beach Association with a two block walk to the beach. You are welcome to enjoy our kayaks, bikes to tour the area and a fire pit.

Hamptons Cottage 3-minute walk to breezy bay beach
Bright, airy 3 bedroom classic Hamptons cottage less than a block from bay beach which is perfect temp and temperament for swimming, wading, paddleboarding and kayaking. Sunsets over the Peconic Bay are amazing especially when you do it with a cold beverage at Tiki Joe’s which has food, drink and fun bands every summer night—only a short stroll away.

Carriage House - Cottage in East Hampton Village
Darling cottage in East Hampton Village. Situated in a historic picturesque tree-canopied neighborhood. Easy stroll to Newtown Lane and Main Street shops. (1/2 mile). Classic atmosphere. Very comfortable, bright, and clean. A perfect place from which to enjoy East Hampton and the surrounding area. Fully renovated (2019).

3 Bedroom Cottage Gem
Traditional Shelter Island house, located in the heart of central village. This 3bedrooms/2 bathrooms house is really quiet, convenient for tennis players with courts cross the street, 4bikes to borrow. This house is close to restaurants and is close to the beach as well...

Cozy Cottage on the Great Pond near beach.
In the heart of wine country is the adorable , nautical inspired cottage surrounded by nature, on a beautiful freshwater pond, a quick walk or bike ride away from a beautiful beach on Long Island Sound. Hiking, fishing, wine tours, farmstands abound!
Popular amenities for cottage rentals in Greenport
Cottage rentals with a hot tub

3 bedroom Hamptons cottage 5 mins from beach

Walk/Bike to East Hampton Village & Ocean Beaches

Lovely 2 BR Beach House No. Shore

Private Room in the House that Art Built

Calf Creek Cottage (Water Mill/Bridgehampton)
Pet-friendly cottage rentals

Seabreeze #4: Charming Cottage Footsteps to Beach

New Suffolk Beach Cottage 1 | North Fork

Chic cottage on lush, secluded acre by the beach.

Cozy Sound-side Cottage steps from beach

Waterfront Cottage With Unforgettable Views

Peaceful cottage, close to beaches

walk to bay, woods cottage

Coastal Cottage | 1 Mi to Town | 2 Cozy Fire Pits
Private cottage rentals

Southampton Village Cottage

East Hampton Fisherman’s Cottage with Secret Bath

*Chic, Family Friendly Hamptons Cottage With Pool

Cozy Cottage Close to the Beach

Cottage in Calverton

Cozy Shelter Island 2 Bedroom 1 Bath Cottage

Beachside Branford- walk to Beach, Grill

Cozy&Chic Beach Cottage (wineries, remote working)
Quick stats about cottage rentals in Greenport

Nightly prices starting at
Greenport holiday rentals start at $614 SGD per night before taxes and fees

Verified guest reviews
Over 190 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Greenport rentals

5 Average rating
Greenport stays are highly rated by guests – averaging 5 out of 5!
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- Yale University
- Foxwoods Resort Casino
- Charlestown Beach
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- Southampton Beach
- Cooper's Beach, Southampton
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- Walnut Public Beach
- Shinnecock Hills Golf Club
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