$21,750
Available: Right Now
Listed: 26/04/2024
Town of Southold, NY, 11944
This condo is one of the nicest decorated in Cliffside. Gorgeous shiplap walls with navy accents. It has a beautiful fireplace, new deck and much more. This unit has the capabilities to be handicap accessible. The master bathroom has a queen size bed...
$11,670
Available: Right Now
Listed: 28/04/2024
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...
$29,010
Available: Right Now
Listed: 28/04/2024
Town of Southold, NY, 11944
High on a bluff overlooking the Sound, this amazing Sound front home has been completely renovated with a chef's gourmet kitchen (fully equipped), bright open living room, panoramic water views from every room. 3 Bedrooms, 2 bathrooms and a huge deck...
$36,750
Available: Right Now
Listed: 28/04/2024
Town of Southold, NY, 11944
One of the nicest spots on the North Fork (that's a quote from a knowledgeable local!), beautifully designer-renovated beach house. 3 bedrooms, 2.5 baths, sleeps 6.Water views from 3 sides of the house, and all bedrooms have water views. Beautifu...
$5,370
Available: Right Now
Listed: 28/04/2024
Town of Southold, NY, 11944
The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern and tasteful American Beech Boutique Hotel, Restaurant & Bar. During your stay, you can explore the vibrant village, natural scen...
$13,710
Available: Right Now
Listed: 26/04/2024
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...
$11,880
Available: Right Now
Listed: 22/04/2024
Town of Southold, NY, 11944
Enjoy this entire home with all the amenities located on a large wooded lot on a quiet private lane. Close to beach, convenient to town. Walk or ride a bike (2 provided) less than 3 miles to downtown Greenport for shopping, bars, and restaurants....
$32,220
Available: Right Now
Listed: 26/04/2024
Town of Southold, NY, 11944
Welcome to our home in the heart of Greenport Village. This beautiful 2,440 sq foot home features 4 bedrooms, 3.5 baths, as well as a queen sleeper sofa in the basement. The house is open, bright and airy, with new stainless steel appliance, gas fire...
$34,080
Available: Right Now
Listed: 26/04/2024
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 ...
$21,000
Available: Right Now
Listed: 22/04/2024
Town of Southold, NY, 11944
Greenport conkling pt creekfront mint 3br cottage w/prime views - This cottage on a half-acre lot fronts on the pristine creek inside Conkling Point with one of the finest estuarine views in the Peconic Bay system. Facing southwest, it is bath...
$5,970
Available: Right Now
Listed: 28/04/2024
Town of Southold, NY, 11944
The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern and tasteful American Beech Boutique Hotel, Restaurant & Bar. During your stay, you can explore the vibrant village, natural scen...
$67,500
Available: Right Now
Listed: 28/04/2024
Town of Southold, NY, 11944
This extraordinarily beautiful, one-of-a-kind beach house is located on 4+ acres with a private beach spanning 1,100' on either side of the Greenport Jetty. Nearly 270 degree views of the water. The property enjoys a spectacular view of Shelter Islan...
$15,000
Available: Right Now
Listed: 22/04/2024
Town of Southold, NY, 11944
Three bedrooms, 2 bathrooms completely renovated home. Sleeps 6. One full bath, one half bath. Outdoor shower. Fully renovated. All bedding freshly washed and beds made, towels, 6 beach chairs and 6 plush beach towels are included. A large air condit...
$10,110
Available: Right Now
Listed: 27/04/2024
Town of Southold, NY, 11944
*Two Week Minimum Rental as per Southold Township requirements. Please message host for more information/availability. This unique home has a style all its own. Stylish and chic, an impeccably restored historic Salt Box. It boasts an updated kitc...
$13,500
Available: Right Now
Listed: 22/04/2024
Town of Southold, NY, 11944
This beautiful house is located in a private beach community. An 8 minute walk brings you to a private beach with views of the Peconic Bay and Shelter Island. Enjoy the complimentary use of two kayaks and two stand up paddle boards, which are easily ...
$6,450
Available: Right Now
Listed: 28/04/2024
Town of Southold, NY, 11944
The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern and tasteful American Beech Boutique Hotel, Restaurant & Bar. During your stay, you can explore the vibrant village, natural scen...
$18,540
Available: Right Now
Listed: 22/04/2024
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...
$12,000
Available: Right Now
Listed: 23/04/2024
Town of Southold, NY, 11944
Discounts available for stays 14 days. Please inquire prior to booking for details.Completely updated, modern and light-filled Cape Cod-style home. You cannot beat this location overlooking the vineyard and only a short walk to the beach or a sho...
$11,280
Available: Right Now
Listed: 23/04/2024
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...
$12,510
Available: Right Now
Listed: 23/04/2024
Town of Southold, NY, 11944
Tennis, swimming, walk to town, sailboats, birds of all kinds in this private community with spectacular views of Sterling Cove and Shelter Island. All new appliances and renovated space with fireplace packed with amenities....
$9,870
Available: Right Now
Listed: 26/04/2024
Town of Southold, NY, 11944
The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern and tasteful American Beech Boutique Hotel, Restaurant & Bar. During your stay, you can explore the vibrant village, natural scen...
$24,240
Available: Right Now
Listed: 26/04/2024
Town of Southold, NY, 11944
Located steps from town, this historic gem is perfect for a weekend getaway. With a spacious kitchen, living and dining spaces as well as a back yard perfect for entertaining and easy walking access to all the best Greenport has to offer, you’ll love...
$25,500
Available: Right Now
Listed: 23/03/2024
Town of Southold, NY, 11944
No extra fees for cleaning, extra guests & Amenities ! Relax in one of America's most beautiful seaside villages, historic Greenport. Walk to the village and within minutes to vineyards, Lavender farm, golf and beaches also Shelter ...
$6,570
Available: Right Now
Listed: 23/03/2024
Town of Southold, NY, 11944
The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern and tasteful American Beech Boutique Hotel, Restaurant & Bar. During your stay, you can explore the vibrant village, natural scen...
$6,570
Available: Right Now
Listed: 23/03/2024
Town of Southold, NY, 11944
The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern and tasteful American Beech Boutique Hotel, Restaurant & Bar. During your stay, you can explore the vibrant village, natural scen...
$15,450
Available: Right Now
Listed: 27/03/2024
Town of Southold, NY, 11944
Family friendly cottage, nestled in a quiet street in Greenport village. The private property has fully fenced backyard, 4 bedrooms, 4 bathrooms, wood burning fireplace, fully stocked kitchen, indoor heating throughout the house, outdoor seating, fir...