$8,100
Available: Right Now
Listed: 04/05/2024
Town of Southold, NY, 11944
We welcome you to our cottage away from it all but still close to all activities that make the North Fork a magical place to visit. Within5 - 15minutes you can walk to all that the Greenport town has to offer and to 2 beaches. No need to have a car a...
$27,330
Available: Right Now
Listed: 02/05/2024
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...
$22,000
Available: Right Now
Listed: 03/05/2024
6 Summerfield Place, Shelter Island Heights, Suffolk County, NY 11965, USA
Charming 6 bedroom Victorian on Shelter Island Sound. Eat-in-kitchen, dining room, master bedroom, and front parlor opening to waterside rocking chair porch. Four Craftsman Victorian bedrooms on second floor, one with a waterfront screened porch. Nea...
$40,000
Available: Right Now
Listed: 03/05/2024
99 Midway Road, Shelter Island, Suffolk County, NY 11964, USA
19L-0033Completely rebuilt 4 bedroom, 3 bath home just a stone's throw from Wade's Beach. Featuring an open plan which includes a living room with fireplace and beamed ceiling, dining area, kitchen with all new appliances and wonderful glassed porch ...
$13,000
Available: Right Now
Listed: 03/05/2024
30 Brander Parkway, Shelter Island Heights, Suffolk County, NY 11964, USA
This charming farmhouse features 3 bedrooms, 3 full baths, open living, dining, and a kitchen with doors out to the large deck with a pool. Located in the Silver Beach area of Shelter Island, it is within close proximity of the most beautiful beaches...
$40,000
$40,000
Available: Right Now
Listed: 03/05/2024
50 Country Club Drive, Shelter Island Heights, Suffolk County, NY 11964, USA
Sited on a gentle rise, minutes from Menhaden Lane beach, the stunning, Philip Johnson's Glass House inspired restoration of this Mid Century Modern home, has brick flooring throughout the main floor and an abundance of natural light. The home has sp...
$24,000
Available: Right Now
Listed: 01/05/2024
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...
$84,000
Available: Right Now
Listed: 04/05/2024
Town of Shelter Island, NY, 11964
This luxury home includes 6 bedrooms with additional sleeping accomodations for 4 in the downstairs walkout recreational room. All bedrooms have ensuite baths, 300 count linens & mutiple pillows & plush towels. The gourmet kitchen is a cook's dream. ...
$20,070
Available: Right Now
Listed: 04/05/2024
Town of Shelter Island, NY, 11964
East Brander EscapeLovely Shelter Island cottage with panoramic bay views, secluded, screened porch, cedar outdoor shower, steps to the beach, access to kayaks and bikes4BR/2BA -waterview, screened in porch perfect for dining inside and out, ...
$60,000
Available: Right Now
Listed: 03/05/2024
7 Hillside Drive, Shelter Island Heights, Suffolk County, NY 11965, USA
Great Shelter Island traditional home in Hilo Shores with a charming wrap around porch. Set up on a hill this spacious home has lovely kitchen, living room, separate den and formal dining. There are five bedrooms and three full bathrooms and a powder...
$12,810
Available: Right Now
Listed: 01/05/2024
Town of Southold, NY, 11944
Charming, private, sun filled 3 bedroom Designer country home with fireplace, spacious living area including den/library, 1.5 baths, modern eat in kitchen and large garden with outdoor dining patio and grill. Less than a stone's throw from 67 Steps B...
$16,560
Available: Right Now
Listed: 02/05/2024
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...
$50,000
$50,000
Available: Right Now
Listed: 03/05/2024
4 B South Ram Island Drive, Shelter Island Heights, Suffolk County, NY 11965, USA
This post-modern summer rental has a large open kitchen, dining and living room with French doors leading out to a large deck with Gunite pool. Separate library with doors leading out to the screened in porch has wonderful sunset views. Two guest roo...
$69,000
Available: Right Now
Listed: 30/04/2024
Shelter Island Heights, NY
Stunning Shelter Island traditional over 3 floors with pool and separate contemporary guest house in luxury settings. Short walk to Sunset Beach, restaurants, tennis and golf. Entertaining space galore, movie screen, wrap around decks, fully private ...
$40,000
Available: Right Now
Listed: 03/05/2024
2 Sylvan Place, Shelter Island Heights, Suffolk County, NY 11965, USA
Beautifully restored iconic Shelter Island Heights Victorian with lovely views of Dering Harbor, Chase Creek, rolling green lawns and a small treed park. Situated within convenient proximity to all that Shelter Island Heights offers with shops, resta...
$10,140
Available: Right Now
Listed: 01/05/2024
Town of Southold, NY, 11944
Charming 2-bedroom cottage located on a family-owned waterfront estate that was converted from a circa 1920s chicken coop. This retreat has inspiring views of Shelter Island and is only steps away from the peaceful waters of the Peconic bay. Describe...
$39,870
Available: Right Now
Listed: 04/05/2024
Town of Shelter Island, NY, 11964
Traditional Hamptons style home with beautiful details, all impeccably renovated. Wrap around porch overlooks expansive front yard. Roomy bedrooms, jetted tubs with separate showers in every bathroom. The primary bedroom suite has a balcony that over...
$90,000
$90,000
Available: Right Now
Listed: 03/05/2024
15 Montclair Avenue, Shelter Island Heights, Suffolk County, NY 11964, USA
Enjoy all The Hamptons have to offer in this newly recreated waterfront home in the heart of West Neck Harbor! Complete with a boat and complimentary captain at the end of your private dock. Every detail was masterfully thought through by a leading d...
$20,000
Available: Right Now
Listed: 03/05/2024
11 Emerson Lane, Shelter Island, Suffolk County, NY 11964, USA
This wonderful cottage on bucolic Shelter Island has been recently renovated and is now available for summer rental. With spacious kitchen with dining table, island seating and breakfast patio outdoors. Large bright living room that looks out to back...
$40,000
Available: Right Now
Listed: 03/05/2024
80 Peconic Avenue, Shelter Island Heights, Suffolk County, NY 11965, USA
Wake up each morning to beautiful views of Peconic Bay. This spectacular Silver Beach location features a 4 bedroom, 2 bathroom cape with country kitchen, living room with fireplace and dining area with French doors opening onto a covered veranda wit...
$10,770
Available: Right Now
Listed: 04/05/2024
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...
$39,450
Available: Right Now
Listed: 01/05/2024
Shelter Island, NY
Please note that a reservation for this property needs to be approved before it is confirmed.Shelter Island Manor Luxurious 2-home estate completely secluded on 8 acres ; Professionally manicured gardens & Heated pool ( <...