$40,470
Available: Right Now
Listed: 04/05/2024
Shelter Island Heights, NY
Beautiful turn-of-the century Victorian Summer Beautiful turn of the century home located on Rainbow Park with breathtaking views of Dering Harbor !Large sunny eat- in kitchen with marble floors and countertops with access to veranda and patio to...
$12,000
Available: Right Now
Listed: 01/05/2024
Town of Southold, NY, 11944
Brand new gut renovation - 3br, 3 full bath unit in the heart of Greenport Village! Have it all - walk to the train and Jitney, town, beach, Shelter Island ferry and more! This second floor unit features large windows and great natural light, central...
$60,000
Available: Right Now
Listed: 06/05/2024
Town of Southold, NY, 11944
LI Sound Waterfront Cottage with 2 Bedrooms and 1 Bathroom. Completely Renovated and Modern Living Space with Open Layout. Home comes complete with Quality Appliances, including Wine Fridge. Approx 1 Acre of Manicured lawn, Private Heated Pool, Viney...
$24,000
Available: Right Now
Listed: 04/05/2024
Town of Southold, NY, 11944
Coastal Vibes: Home with waterviews, short distance from a secluded beach on Pipes Cove overlooking Shelter Island. Beach/ water access is a 0.4mile walk. The bay is across the street for views. Home features 4 bedrooms and 2 full bathrooms (plus out...
$11,670
Available: Right Now
Listed: 04/05/2024
Town of Southold, NY, 11944
Our house is an historic Dutch colonial, both cozy and spacious, with warm wood trim and wood floors throughout. The 20 x 20ft. Great Room, a perfect gathering space for family and friends is complete with a baby grand piano, cable TV, children's toy...
$22,890
Available: Right Now
Listed: 01/05/2024
Town of Southold, NY, 11944
Fully Renovated Townhouse walking distance to town, beaches, parks, brewery and short bike to wineries. Brand new Kitchen, bathrooms & bedrooms. Enjoy all the North Fork has to offer: wineries, breweries, amazing restaurants, shops and beaches! 3 Bed...
$52,380
Available: Right Now
Listed: 06/05/2024
Town of Southold, NY, 11944
Snug Harbor StylishPristine waterfront home with direct access to private bay and dock, primary bedroom balcony, spacious deck with grill, multiple outdoor lounge areas, minutes to Greenport village and local beaches!3BR/4BA:Nautical-themed i...
$27,750
Available: Right Now
Listed: 06/05/2024
Town of Southold, NY, 11944
2024 Rates: MD-June $28k, June $25k July $35k , Weekly rental$8,500/week 2 week minimum. Luxurious living in Greenport's private Rock Cove Estates. A stone's throw away to the deed private beach on the Long Island Sound. Highly desirable area where y...
$18,540
Available: Right Now
Listed: 04/05/2024
Town of Southold, NY, 11944
Seaside Greenport Village HistoricDistrict, on Long Island’s North Fork, New York.“Rose Cottage” is within the Greenport Village Historic District with water views of Sterling Harbour’s busy mooring field of classic to modern sailboats, and p...
$22,080
Available: Right Now
Listed: 06/05/2024
Town of Southold, NY, 11944
Stay in our wonderful Greenport home on one of the quietest blocks in the area. Enjoy a short 10-minute walk into town. Stroll down Main Street where you can find great restaurants, coffee shops, bakeries, bike rentals, and artisanal shops. Norman E....
$26,970
Available: Right Now
Listed: 06/05/2024
Town of Southold, NY, 11944
Gorgeous 4 bedroom, 3.5 bath house with a fenced in pool, primely located close to everything Greenport has to offer & in a quiet development. This beautiful home is a short walk to the private beach & conveniently 2.5 miles from the village. Enjoy a...
$71,250
Available: Right Now
Listed: 04/05/2024
Shelter Island Heights, NY
This extraordinary modern home offers an abundance of amenities with easy access to the white sands of Sunset Beach. Perched on .71 of an acre, this 3,200 square feet of open living space brings the outdoors inside effortlessly in an elegantly design...
$12,030
Available: Right Now
Listed: 01/05/2024
Town of Southold, NY, 11944
Greenport Village Vacationer's DelightOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape the hustle and bustle of everyday life at this lovely, newly-...
$11,460
Available: Right Now
Listed: 06/05/2024
Town of Southold, NY, 11944
Modern on 9th Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Originally an old-time candy and soda shop this 1957 home is truly a charmer. Recently updat...
$8,370
Available: Right Now
Listed: 04/05/2024
Town of Southold, NY, 11944
2024 availability !Looking to escape the city for a couple of weeks or even a month? The house is well set up for working remotely and we are pet friendly!We value inclusion and respect and happily welcome guests of all backgrounds....
$35,730
Available: Right Now
Listed: 06/05/2024
Town of Southold, NY, 11944
An outdoor oasis is one element of this extraordinary property. This one of a kind 5 bedroom, 3.5 bath residence is the perfect home to make special memories this season. The perfect rental with one of the most extraordinary pool and garden areas on ...
$7,500
Available: Right Now
Listed: 04/05/2024
Town of Southold, NY, 11944
Lovely Victorian home with private entrance, porch, and brick patio. Floor to ceiling windows in light filled large bedroom with en suite bathroom. Cozy den has a beautiful bay window and a queen size pull out sofa bed for additional guests. Sunny si...
$16,470
Available: Right Now
Listed: 06/05/2024
Town of Southold, NY, 11944
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 rest...
$33,330
Available: Right Now
Listed: 06/05/2024
Town of Southold, NY, 11944
This brand new modern home offers everything you could ask for from a summer retreat in Greenport. Two story height great room with gas fireplace, a seamless layout with bonus room that includes shuffleboard, ping pong and pool table. Large balcony w...
$15,390
Available: Right Now
Listed: 06/05/2024
Town of Southold, NY, 11944
Beautifully appointed townhouse in coveted Stirling Cove Condominiums. Enter a light filled room with magnificent views of the cove and bay. Featuring newly renovated, spacious kitchen, dining room, elegant living room with wood burning fireplace, wa...
$16,500
Available: Right Now
Listed: 06/05/2024
Town of Southold, NY, 11944
Cozy Greenport CottageOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to Maple Street Manor, managed by Vacasa. This house is located in Greenport...
$8,010
Available: Right Now
Listed: 05/05/2024
Town of Southold, NY, 11944
Combine peace and quiet with bustling downtown action when you book this charming Greenport vacation rental! The 1-bedroom, 1-bath apartment sits on a peaceful side street right off of Main Rd., allowing you easy access to unique shops, restaurants, ...