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The BEST Winter Rentals listings near Southold, Suffolk, Riverhead, Shelter Island NY

The BEST Winter Rentals listings near Southold, Suffolk, Riverhead, Shelter Island NY

Click here to post your own
Rentals listing
with Times Review Digital Classifieds
Click here to post your own
Rentals listing
with Times Review Digital Classifieds

Winter Rentals 

CUTCHOGUE: Creekfront cottage. 3 small BRs, 2 baths, open plan DR, LR, kitchen. Sunroom, garage. $3,500/ month plus utilities. Security. Available 11/1- 6/1. 516-984-5164.
 
CUTCHOGUE: Unique 1830s restored barn. 2 BR, 1 bath, privacy, walk to village. Available 10/1/24- 5/1/25. $3,000/ month. Call Douglas Elliman Real Estate, 631-354-8100.
 
MATTITUCK: 9/1/24- 5/31/25. New 1 BR, 1.5-bath cottage. Walk to town. $2,700/month. 516-296-0038.
 
Orient: Charming 3 bedroom, 2-bath home in Orient Village from October through May. $2,500/month plus utilities. References, credit check required. 305-304-4380.
 

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Rentals
CUTCHOGUE: Unique 1830s restored barn. 2 BR, 1 bath, privacy, walk to village. Available 10/1/24- 5/1/25. $3,000/ month. Call Douglas Elliman Real Estate, 631-354-8100.
Rentals
GREENPORT: Corner retail store in business district. $2,500 /month plus utilities. Additional square footage available. 631-477-2904.
Rentals
MATTITUCK: 1 BR walk-in. CAC. Recently renovated. No pets/smoking. Credit check, application fee. $2,100/month plus utilities. 631-871-3636.
Rentals
Shelter Island: Large year-round 1 BR apartment in central location. $2,200/month plus utilities. 631-902-4402.
Rentals
NORTHVILLE: Furnished cottage; steps to the beach. 3 BR, heated. Month of September, $3,000. Pictures available upon request. 631-722-3248.
Rentals
LOOKING FOR BARN SPACE or barn to rent: From Calverton to Cutchogue. 631-255-8507.
Rentals
Orient: Charming 3 bedroom, 2-bath home in Orient Village from October through May. $2,500/month plus utilities. References, credit check required. 305-304-4380.
Rentals
AQUEBOGUE: Indoor/outdoor. Boats, trailers, vehicles, campers, etc. Call 631-722-1221.
Rentals
Cutchogue: 800-square-foot office on second floor on Route 25. Handicapped accessible. 631-902-4402.
Rentals
CUTCHOGUE: Creekfront cottage. 3 small BRs, 2 baths, open plan DR, LR, kitchen. Sunroom, garage. $3,500/ month plus utilities. Security. Available 11/1- 6/1. 516-984-5164.
Rentals
greenport Village: New studio/loft apartment. W/D, CAC, large deck, cathedral ceiling. $2,075/month. 516-241-8135.
Rentals
MATTITUCK: In the heart of the village. Private, sunny first-floor office. Freshly painted; well-maintained building. 225 sq. ft. $850/ month. All utilities included. 516-458-0001.
Rentals
AQUEBOGUE: For 2025. 1- 2 BR cottage on the water. 631-722-4096.
Rentals
GREENPORT: Waterfront. Furnished 1 BR cottage. Available September through May 2025. $3,500/month including utilities. References required. 631-804-8395.
Rentals
MATTITUCK: 9/1/24- 5/31/25. New 1 BR, 1.5-bath cottage. Walk to town. $2,700/month. 516-296-0038.






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