$36,750
Available: Right Now
Listed: 22/04/2024
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...
$20,970
Available: Right Now
Listed: 22/04/2024
Town of Southold, NY, 11944
Spacious Greenport 2600 square foot Four Bedroom Cottage Beach Bungalow. Five minute waking distance to Greenport Village (restaurants, bars, coffee shops, shopping and much more) Near 5th & 6th Street Beach & Park , Shelter Island Ferry, Train and C...
$24,000
Available: Right Now
Listed: 22/04/2024
Town of Southold, NY, 11944
Our Greenport beach house is steps from Pipes Cove Beach with beach access, water views from the house, a big yard, and a short drive or bike ride into Greenport Village.This 4 bedroom, 2 bathroom home between Southold and Greenport Village rests...
$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...
$31,920
Available: Right Now
Listed: 22/04/2024
Town of Shelter Island, NY, 11964
Enjoy this newly renovated home on Shelter Island. A gorgeous, well-stocked gourmet kitchen with vaulted ceiling great room allows the chef(s) to be a part of the fun. Sliders out to the pool and tons of outdoor seating provide plenty of options for ...
$23,250
Available: Right Now
Listed: 22/04/2024
Town of Shelter Island, NY, 11964
Privately located on a wooded hill near Wades Beach (5 minute walk) and Fresh Pond (1 minute walk). Open concept floor plan. Clean lines and modern furniture. Chef's kitchen with Viking appliances.Spacious deck off the living room perfect for lou...
$26,010
Available: Right Now
Listed: 26/04/2024
Town of Shelter Island, NY, 11964
Fabulous open floor plan featuring soaring ceilings, striking stone fireplace, designer furnishings, and gourmet fully equipped kitchen for the discerning cook. This 4 bedroom/3.5 bath beautiful home is private, nestled among mature trees and set far...
$23,970
Available: Right Now
Listed: 24/04/2024
Town of Southold, NY, 11944
Please read full description ! Rental registry # 0952Private modern cabin near the bay situated on 3.8 acres on culdesac. The cabin is set 200 ft off a quiet culdesac that lies across the street from Gull Pond. Separated on three sides by ...
$17,130
Available: Right Now
Listed: 22/04/2024
Town of Shelter Island, NY, 11964
Summer 2023 calendar has been updated ! The month of July is now available and can be rented for the entire period or in 2 week blocks- August 1-18 is also available Please note 2 week minimum rental period This serene, modern sun drenched spacio...
$36,750
Available: Right Now
Listed: 22/04/2024
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...
$53,340
Available: Right Now
Listed: 19/04/2024
Town of Shelter Island, NY, 11964
Please note that a reservation for this property needs to be approved before it is confirmed.Wake up smiling every morning in this sun-filled house. Spend days lounging and evenings grilling and dining around the 40’ long pool. Relax inside on th...
$12,750
Available: Right Now
Listed: 25/04/2024
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...
$42,870
Available: Right Now
Listed: 22/04/2024
Town of Shelter Island, NY, 11964
Sunny and bright spacious home with 4 bedrooms, 2 living rms, laundry and office.Perfect home to enjoy any season6 min from ferrylocated on Menantic Creekbedroom 1 has king bedbedroom 2 and 3 have queensbedroom 4 has 2 twins...
$5,970
Available: Right Now
Listed: 22/04/2024
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...
$29,490
Available: Right Now
Listed: 26/04/2024
Shelter Island Heights, NY
Beat the heat in this fabulous summer retreat on laid back Shelter Island. Restaurants, antiquing, wineries, hiking, biking, paddle-boarding, kayaking, tennis, golf and of course the beach are all yours to be had at this special gem in the genteel pa...
$9,750
Available: Right Now
Listed: 26/04/2024
Town of Southold, NY, 11944
Designed and built in 2003, this cozy house has water views of Peconic Bay, enormous glass skylights, fully equipped kitchen, two bedroom, two bath, washer, dryer, Wifi, flat screen tv, private rose garden, outdoor studio/bedroom, private parking, a ...
$17,640
Available: Right Now
Listed: 19/04/2024
Town of Shelter Island, NY, 11964
Huge 4 bedroom, 2 1/2bathroom home on heavenly Shelter Island. Minutes to beach and town. Overlooks a tranquil pond. Large grounds and deck, Kawai grand piano. Cathedral entrance, breakfast room, with bay windows, dining room, fireplace, laundry room...
$31,110
Available: Right Now
Listed: 23/04/2024
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...
$30,390
Available: Right Now
Listed: 25/04/2024
Town of Southold, NY, 11944
Bachelorette, weddings and big party escape.Go fishing, boating, hiking, golfing, antique shopping etcwalk to town, walk to beach,walk to vineyard, walk to restaurantsEnjoy Greenport, named by Forbes magazine one of the 11 prettiest t...
$64,800
Available: Right Now
Listed: 22/04/2024
Town of Southold, NY, 11944
This brand new construction house is perfect for large groups. Gather with friends and family in the double height ceiling open concept living room/dining room/kitchen area. Soak up the sun lounging by the pool. Take a super short walk to town to enj...
$12,750
Available: Right Now
Listed: 22/04/2024
Town of Southold, NY, 11944
Cliffside Resort is located on a bluff overlooking the Long Island sound with beautiful water vistas. The resort has an in ground heated pool and beautiful landscaped lawns. Direct beach access, bbqs, laundry facilities, and many other activities. Pa...
$21,750
Available: Right Now
Listed: 19/04/2024
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...