$33,780
Available: Right Now
Listed: 07/07/2024
Town of Southold, NY, 11944
Beach front with a private beach. Ideal for sunbathing, swimming, fishing & kayaking. Enjoy daily gorgeous sunset views from the beach, the house and the spacious deck. Outdoor dinning BBQ area. One side of the deck has the firepit area and the other...
$7,500
Available: Right Now
Listed: 07/07/2024
Shelter Island Heights, NY
Come stay in the heart of Shelter Island, central to all beaches, shopping, and restaurants. Spacious 3 bedroom ranch sleeps up to 6, with blissfully comfy "W Hotel" beds. Bedroom lamps have built-in USB ports for charging your phone. Living room wit...
$25,230
Available: Right Now
Listed: 08/07/2024
Town of Shelter Island, NY, 11964
Beautiful Waterfront Home on West Neck Creek on Shelter Island. New deck overlooking West Neck Creek -Great for relaxing or entertaining. Bright & Airy vacation home on private road. Newly decorated with central air conditioning, pool/game room. Larg...
$50,850
Available: Right Now
Listed: 08/07/2024
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...
$33,270
Available: Right Now
Listed: 07/07/2024
Town of Southold, NY, 11944
Enchanted home with beautiful bay views. This house has it all. Modern updates with old-world charm. Gorgeous chefs kitchen, hardwood floors throughout, stone and marble baths. Located in the center of Greenport, Walk to town. Lovely renovations thro...
$27,060
Available: Right Now
Listed: 07/07/2024
Town of Southold, NY, 11944
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 a private backyard.This home is walking distance to many restaurants...
$18,480
Available: Right Now
Listed: 07/07/2024
Town of Shelter Island, NY, 11964
This fresh and inviting 3 bedroom, 4 bath cottage on 1.12 +/- acres has been completely renovated. Some of the many highlights are a sunny open layout including living room with elevated ceilings, dining area with adjacent screened porch and entertai...
$45,000
Available: Right Now
Listed: 01/07/2024
Town of Shelter Island, NY, 11964
Newly renovated sun-drenched Shelter Island retreat featuring a stunning contemporary art collection and set on one acre of lush private garden and close to the South Ferry. The heated gunite saltwater pool is built into 2500 square feet of mahogany ...
$32,580
Available: Right Now
Listed: 07/07/2024
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, outdoor seating, and gas grill. The property is in a doub...
$32,400
Available: Right Now
Listed: 07/07/2024
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...
$18,420
Available: Right Now
Listed: 08/07/2024
Town of Southold, NY, 11944
A quiet Cape home within walking distance to all Greenport Village has to offer - dining, shopping, the beach and transportation hub. A perfect getaway for families, couples or friends who want to explore the North Fork, including wineries, breweries...
$27,420
Available: Right Now
Listed: 08/07/2024
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...
$29,010
Available: Right Now
Listed: 08/07/2024
Shelter Island, NY
This is a magical house. It is surrounded by woods and a pond. The only sounds you hear are the birds and other animals, the wind in the trees. It is a one minute walk to Dering Harbor where the sunsets are neon pink. Upstairs, a glass room that ...
$37,800
Available: Right Now
Listed: 07/07/2024
Shelter Island Heights, NY
This is a 2 house property that can sleep up to 15 if necessary. The Main house has 4 bedrooms and 3 baths, while the cottage has 3 bedrooms and one bath -- as well as an outdoor shower! You can rent one or both--it is up to you! The homes sit on a l...
$23,730
Available: Right Now
Listed: 08/07/2024
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...
$30,000
Available: Right Now
Listed: 06/07/2024
Town of Southold, NY, 11944
Welcome to this stunning & newly renovated Greenport home. This magnificent home seamlessly blends comfort, style and luxury living. The home provides a bright & airy feel throughout amongst its two levels of living. The first floor provides two spac...
$38,610
Available: Right Now
Listed: 07/07/2024
Shelter Island Heights, NY
Please contact us if you are interested in booking a month or longer stay for the 2024 summer season.An impeccably restored and charming Victorian summer cottage originally built in 1876 and located in the heart of historic Shelter Island Heights...
$19,110
Available: Right Now
Listed: 07/07/2024
Town of Southold, NY, 11944
Luxury 2 bedroom, first floor apartment located across the street from Townsend Manor Marina in the heart of Greenport Village . Walk to town and enjoy the amazing restaurants and shopping that Greenport has offer. This custom Victorian Farmhouse has...
$17,730
Available: Right Now
Listed: 07/07/2024
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...
$22,800
Available: Right Now
Listed: 07/07/2024
Town of Southold, NY, 11944
Newly restored antique home, 3 bedrooms, 1.5 baths with outdoor shower surrounded by manicured lawn & bucolic grounds. Sunlit and immaculate, decorated in a simple seaside style. Three cozy, fresh bedrooms with full closets. 1.5 Baths wit...
$18,270
Available: Right Now
Listed: 06/07/2024
Town of Southold, NY, 11944
Modern, brand new, house, with private beach, for rent. Experience North Fork summer living in this newly constructed gem! Nestled in the sought-after Stirling Eastern Shores community, this impeccably designed modern farmhouse offers exclusive a...
$67,500
Available: Right Now
Listed: 04/07/2024
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...