$2,325 per month
1750 W Main St Unit C04, Riverhead, NY 11901
**Ask About Our Rent Specials*. $99 Sec.Dep Special*. Restrictions Apply** Beautiful Courtyard Setting for a Deluxe Bedrooms White Shakerel Kitchen Cabinetry. Heat, Hot Water & Cooking Gas Included. Some With Terraces. Detached Garages Available. Minutes To the L.I.E. Exit 72 And Local Transportation. Prices/policies subject to change without notice.
Michelle Holmes Fairfield Properties
$15,000 per month
930 W Cove Rd, Cutchogue, NY 11935
**2026 Rates** May $15K, June $18K, September 8-30 $12K, October $12K. This property is a stunning waterfront home located on West Cove in the exclusive Nassau Point area. Offering breathtaking views of the Great Peconic Bay, Robins Island, and New Suffolk, this home exudes charm and sophistication. The main level boasts two spacious great rooms, an enclosed three-season room, an eat-in kitchen,
William Walters Daniel Gale Sothebys Intl Rlty
$3,500 per month
248 5th Ave, Greenport, NY 11944
This Completely Renovated One-Of-A-Kind Historic Religious Structure was built in 1879. Stylish And Close To Everything In Greenport. Soaring Cathedral Ceilings, Mesmerizing European Stained Glass Windows, Brand New Kitchen And Full Bath. Located In The Heart Of The Much Coveted Greenport Village. Moments Away From Top Restaurants, Trendy Stores, A Sugar Sand Local Beach, The LIRR Station, And
Peter Halpin Douglas Elliman Real Estate
$7,000 per month
8 Oyster Point, Greenport, NY 11944
GREENPORT WATERFRONT CONDO . Enjoy your life in this well- appointed Bayfront 2 bedroom, 2 bath condo with stunning views of Shelter Island and Greenport Harbor. Amenities include a waterfront pool, tennis & pickle ball court, 200 Ft of private sandy bay beach, and your own boat slip in the private marina. Located just a short distance to shops and restaurants in Historic Greenport Village, ferry
Jeanmarie Bay William Raveis New York LLC
$1,995 per month
1355 Roanoke Ave Unit 12Lh, Riverhead, NY 11901
*Ask About Our Rent Specials*. Restrictions Apply* Centrally located at the crossroads of Long Island's North and South Forks at Route 58 near many east end landmarks. Visit farms, wineries and the Peconic Bay and downtown Riverhead shopping village. Long Island Expressway Exit 72.
Michelle Holmes Fairfield Properties
$10,000 per month
870 Stars Rd, East Marion, NY 11939
Beautiful North Fork home within walking distance to the beach, as well as numerous vineyards, restaurants, and local shops. Upon entering this home, you will enjoy spacious living quarters full of natural light and comfortable furnishings. The perfect mix of modern comfort, the gourmet kitchen boasts stainless steel appliances, gleaming countertops, and a large center island with a breakfast
Christine Brown Netter Real Estate Inc
$15,000 per month
1800 Westphalia Rd, Mattituck, NY 11952
June $15,000 (rented June 30-August 15)Rustic luxury on the North Fork! Located within a waterfront enclave in Mattituck and close to all creature comforts, this renovated barn will not disappoint. 5 bedrooms, 3.5 bathrooms, heated pool, large EIK and den, views of Mattituck Inlet and access for kayaking, swimming and paddleboarding. A short stroll into all Mattituck has to offer... Strong's
Sheri Winter Parker Corcoran
$24,200 per month
1100 Alvahs Ln, Cutchogue, NY 11935
Available July 2026 for $34,500Available August to September 7, 2026 for $42,000Come and enjoy the privacy that lies behind the doors of this reimagined modern ranch. Once inside you will be thrilled by the level of detail in this 2023 gut renovation. As you enter the home, you are welcomed with expansive views across the large backyard onto the surrounding vineyards. The 14' lofty
Sheri Winter Parker Corcoran
$32,000 per month
1080 Lands End Rd, Orient, NY 11957
Very spacious, architect's own custom designed beauty just 3 minutes to gorgeous, private community LI Sound beach. 44' x 24' heated, saltwater pool. Natural light filled, open concept design LR/DR/KI with sliders to expansive deck overlooking private, fully fenced, park-like grounds. 2nd floor features a large, 2nd living room with billiards, foosball, large tv plus sliders to private deck. 2
Kathleen Travers Douglas Elliman Real Estate
$8,000 per month
400 Hill Rd, Southold, NY 11971
Welcome to your perfect summer getaway located in the desirable Claves Neck neighborhood of Southold. This comfortable Ranch has ample space for the whole family to unwind and recharge after a day of exploring the North Fork. The home offers a fully equipped kitchen, spacious living, and dining rooms, three pleasant bedrooms, two pristine bathrooms. Outside, a savor al fresco dining amid the lush
Jeanmarie Bay William Raveis New York LLC
$25,000 per month
910 Glenn Rd, Southold, NY 11971
Introducing your perfect retreat! This stunning 4-bed, 3.5-bath waterfront oasis nestled on West Creek in Southold. Enjoy access to Peconic Bay via your private dock. Spanning approx 3500 sq ft, revel in the elegance of oak floors, a luxurious soaking tub, and high ceilings throughout. The 1st floor has 2 primary ensuites, a spacious Great Room with cozy fireplace, laundry, and 2.5 baths +2-car
Andrea Parks Douglas Elliman Real Estate
$19,000 per month
300 Marion Place, East Marion, NY 11939
Private, peaceful home on a serene acre of property with mature plantings and wonderful landscaped greenery. Just renovated, featuring open modern Kitchen/Dining combo for modern entertaining. Separate family room across open foyer with fireplace and loads of puzzles & games. Charming covered front porch looks out onto expansive front yard. Back deck with grill overlooks pool and backyard. (Pool
Laura Wanamaker Howard Hanna Coach
$36,000 per month
950 Tasker Ln, Greenport West, NY 11944
2026 Rates: May $26,000; June $29,000; July $36,000; September $27,000; October $24,000. 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 access to a private Long Island Sound beach, just a five minute walk from the property. Step inside to discover a
William Walters Daniel Gale Sothebys Intl Rlty
$28,000 per month
1100 Pine Ave, Southold, NY 11971
Permit #: 0160. This Superb 3-Bedroom, 2-Bathroom Ranch Home Showcases Gorgeous Water Views And Is Strategically Located Near Goose Creek Beach And The Pulsating Heart Of Southold, Allowing You To Enjoy The Best Of Both Worlds. The Interior Is Beautifully Designed With A Minimalist Aesthetic, Offering A Serene Retreat From The Every Day Hustle And Bustle. The Open Layout Allows For Easy Movement
Colin McCarthy Thomas J McCarthy Real Estate
$4,500 per month
220 Fiddler Ln, Greenport, NY 11944
Charming, clean and tastefully decorated, 3 bedroom,1 bath (plus an outdoor shower) Greenport bungalow. The enclosed sun-porch is a great extra space to relax on rainy days too. The location~ Just a couple of blocks from a beautiful Bay Beach with boat ramp and amenities. Just down the block from Portobello's Restaurant, Billy's By The Bay and Kontakosta Vineyard. Close to Village shops, vintage
Rita Rooney Douglas Elliman Real Estate
$7,000 per month
Unlisted Address
Experience the charm of this delightful rental cottage nestled in Southold, North Fork, just a stone’s throw from Founder's Landing Park and Wharf House, with one of the most amazing sugar sand beaches in our community. This unique, fully furnished one-bedroom retreat features flexible rental periods and competitive rates throughout the year.Imagine waking up to the serene views of a
Nicholas Planamento William Raveis New York LLC
$6,900 per month
11 Beach Rd, Jamesport, NY 11947
North Fork. Beauty and the Beach at 11 Beach Road, Jamesport. Open Bayfront Right On The Bay Beach! Private "Fairhaven" Community, stunner mid century modern. Available Winter Months at $6,900 per, August thru Labor Day Tues the 8th $35,000. 5 weeks this year! Sand in your toes right out your door, full walls of glass, gorgeous open bay views from every room. Sparkling hot tub spa for 6 added to
Kate Carpluk William Raveis New York LLC
$15,000 per month
530 Stillwater Ave, Cutchogue, NY 11935
Perfect summer getaway! 3 bedrooms, 2.5 bathrooms, in-ground pool, close to beach, business district, vineyards and restaurants. 30 day minimum stay.
Erin Kaelin Signature Premier Properties
$5,500 per month
1600 Westview Dr, Mattituck, NY 11952
**RENTED JULY & AUGUST 2026*** [2026 Availability & Pricing as Follows: Off Season October 1st - April 30th: $5,500/mo. May (Incl Memorial Day): $10,000. June: $12,000. July 1-31: $15,000. August - Labor Day: $21,000. September (not including LD): $10,000. Escape to the North Fork and enjoy the perfect blend of comfort & coastal living in this meticulously maintained 3-bed, 3-full bath home. As
Mariah Mills Daniel Gale Sothebys Intl Rlty
$8,000 per month
415 Southern Cross Rd, Cutchogue, NY 11935
Perfect summer cottage. Location can't be beat! A stone's throw to serene Pequash beach. Nestled in quiet Fleet's Neck with 2 bay beaches within walking distance. Well maintained home. Available for summer or short term off-season rental., Additional information: Lease Term: August-Labor Day, Flexible, July, July-August, June, Memorial-Labor Day, Off Season. 30 day minimum
Erin Kaelin Signature Premier Properties
$4,000 per month
1975 Youngs Ave, Southold, NY 11971
This beautifully furnished farmhouse offers you a warm welcome home on the North Fork. Amazing decor throughout every room for you to enjoy your stay. There are three bedrooms and two full bathrooms, hardwood floors, central air conditioning, and a back deck overlooking a fenced in yard. Great location just one block from the town restaurants, shops, and all transportation. Numerous beaches to
Barbara Poliwoda Douglas Elliman Real Estate
$40,000 per month
2430 Dignans Rd, Cutchogue, NY 11935
Cutchogue North Fork: Spend August-LD 2027 in this beautifully appointed & very private Long Island Sound front home at 2430 Dignans Road, Cutchogue: come find out why the owners call it North Cliff. Spectacular decks & pool set high on the cliffs overlooking the LI Sound - private easy steps to beach. On the other side forever views of Oregon Road farmland. Published in international Fashion
Nicholas Planamento William Raveis New York LLC
$24,000 per month
400 Diamond Ln, Peconic, NY 11958
Memorial Day – Labor Day: $24,000.00 // June: $6,000.00 // July: $10,000.00 // August: $12,000.00 Enjoy stunning water views and all-season access to the Sound from this charming 3-bedroom, 1-bathroom waterfront home. This cozy home channels happy, mid-century vibes. Large living room with fireplace, dining nook, and sunroom, all with breathtaking views of the water. The patio with BBQ is the
Sheri Winter Parker Corcoran
$60,000 per month
355 Windjammer Dr, Southold, NY 11971
This soothing beach house is so Zen, you will feel like you are at a spa retreat! Peaceful and perfectly appointed, the backyard features a fabulous lagoon style pool, with a waterfall and hot tub, an amazing outdoor kitchen and bar, bathroom and outdoor shower! 3 bedrooms, 2 baths, including a spacious primary suite with a gorgeous spa like bathroom. All this and steps to the association beach!
Sheri Winter Parker Corcoran
$22,500 per month
189 Old Harbor Rd, New Suffolk, NY 11956
2026 Rates: July 20-31; A1–LD: $22,500; Sept 1–30: $7,500; October: $7,500: Pristine Mid Century Modern Waterfront with 200' Of Private Sugar Sand Beach on sprawling 2 acre parcel! Property Features Breathtaking Views Of Robins Island, Southampton And Nassau Point. Chic Furnishings Adorn This Lovely Home Along with Interior Panoramic Views Of The Great Peconic Bay. Open Living Space with High
William Walters Daniel Gale Sothebys Intl Rlty
$22,000 per month
Unlisted Address
Mattituck, North Fork: Sunshine and solace await you in this immaculate and recently renovated vacation home with a brand NEW, heated, saltwater pool (16x34 gunite)! Large open and bright rooms with lots of natural light allow you to relax in comfort and enjoy your time off. Home accommodates a maximum of 6 guests and features first floor bedroom with luxurious bath, open concept dining
Nicholas Planamento William Raveis New York LLC
$20,000 per month
25 Moose Trail, Cutchogue, NY 11935
Discover the perfect blend of comfort and luxury in this stunning 4-bedroom Cape, ideally situated in the heart of Cutchogue. Designed for both relaxation and entertainment, this home features a chef’s kitchen and an array of spacious living areas, including a formal dining room, game room with a pool table and arcade games, plus a first-floor bedroom and full bath—all tastefully furnished. Step
Jeanmarie Bay William Raveis New York LLC
$19,500 per month
1355 Watersedge Way, Southold, NY 11971
Welcome to 1355 Watersedge Way, a delightful Bayfront home offering breathtaking water and sunset views in Southold. Nestled next to a nature preserve with 300 feet of private beach, this home provides both serenity and direct water access.Inside, the spacious living room features a smart TV and a wall of sliding glass doors that open to a waterside deck, perfect for enjoying the bay breeze.
Jeanmarie Bay William Raveis New York LLC
$7,500 per month
3400 Youngs Ave, Southold, NY 11971
Permit #493 Newly Renovated Farmhouse Centrally Located In Southold With Easy Access By Bus, Train or Car. Enjoy Your Morning Coffee As The Sun Rises Over The Farm Field. Spend An Afternoon Exploring The Beauty of the North Fork, Soak in the Sun at one of the Beautiful Peconic Bay or Long Island Sound Beaches, Enjoy Live Music at Numerous Wineries and/or Breweries, Browse unique local finds at
Thomas McCarthy Thomas J McCarthy Real Estate
$12,000 per month
250 Wesland Rd, Southold, NY 11971
NEW TO THE RENTAL MARKET! JUST A DREAM BOAT! NEWLY RENOVATED, LIGHT AND BRIGHT, BEAUTIFULLY APPOINTED, EVERY CONVENIENCE - 2 BEDROOMS, 2 BATHS. PLUS - CONVERTIBLE QUEEN SOFABED! BEAUTIFUL OUTDOOR DINING, FIRE PIT, PORCH, ENCLOSED SHOWER! PRICED RIGHT! STEPS TO POPULAR KENNEY'S BEACH - JUST BRING YOUR LITTLE RED WAGON AND STROLL TO THE BEACH AND ENJOY! Additional information: Appearance excellent!
Marie Beninati Beninati Associates
$30,000 per month
3655 Pequash Ave, Cutchogue, NY 11935
GORGEOUS SEASONAL (and Off-Season) RENTAL AVAILABLE -- FLEET's NECK! Walk to Beach from your Private FABULOUS OASIS. 4 Bedroom and 2 Full Bath Contemporary Home on tucked away Lot Set Well-Back from Road on 1 + acres. Offers Sleek Main Floor Living Area with Fireplace, Chandeliered Dining Area, Foyer, Light Bright Kitchen with All Stainless-Steel Appliances, that leads to a Furnished 2-Level Deck
Deirdre Fedun Fedun Real Estate Inc
$79,000 per month
Unlisted Address
Cape-Cod-Style Cedar-Shingle House situated on edge of low bluff. Wooded lot with 2nd-story master bedroom suite/deck. Fantastic 180-degree views of Gardiner's Bay, Bug Lighthouse, Shelter Island, Orient Village and East Hampton with 150-feet of private sandy beach and boat mooring. Permit #0049., Additional information: Appearance:Excellent, Interior Features:Separate Thermostat
Anna Carlino Douglas Elliman Real Estate
$12,500 per month
455 Fred St, New Suffolk, NY 11956
Looking for the perfect getaway? Look no further than this charming 3 bedroom, 2 bath seasonal rental, located just minutes away from everything you need to make your vacation unforgettable. With its prime location just a short walk from New Suffolk Beach, Legends & Minnow restaurants, the New Suffolk Marina, and local wineries, golf, and farms, this rental is the perfect home base for all your
Nicole Fitzgerald Signature Premier Properties
$30,000 per month
650 Pine Ave, Southold, NY 11971
A masterfully crafted resort style property, where coastal luxury meets effortless living. Tucked within a coveted private beach community with beach access, this resort-style property was designed for gathering, entertaining, and unwinding in total privacy. The home features a show-stopping 20’ x 40’ heated saltwater pool, framed by lush, manicured grounds that feel both serene and indulgent.
Colin McCarthy Thomas J McCarthy Real Estate
$3,500 per month
3825 S Harbor Rd, Southold, NY 11971
Classic North Fork Beach home located just 10 homes away from South Harbor Beach and Park, Amazing comfort and privacy on this acre plus setting. Home is crisp, clean, and fully furnished ready for you to enjoy. South Harbors expansive beach offers an inlet to paddle board, kayak, fish, and relax on the water. Please call for availability; 2025 Rates: January- April $3500, May $5000, June $7000,
Barbara Poliwoda Douglas Elliman Real Estate
$18,000 per month
355 Midway Rd, Southold, NY 11971
Available seasonally, this impeccable modern 3 bedroom 3 bath home in Southold's coveted Cedar Beach district offers privacy, water views and a private neighborhood beach. The open plan includes kitchen, dining area, den/office, and living room with fireplace. Sliding doors open to the bluestone patio with gas grill and plenty of room for entertaining and sunning. The three bedrooms, including a
Marianne Collins Brown Harris Stevens N Fork
$20,000 per month
950 Blue Marlin Dr, Southold, NY 11971
Beachfront, located in Southold Shores, this architect's own home is built with all the beautiful appointments you can imagine. Embracing the purity of architectural detail, together with a refined simplicity, this waterfront home offers a timeless elegance. Sweeping sunsets eye-catching angles and thoughtful details provide constant visual interest. A large 4 bedrooms with 4 baths ensuite,
Lori Feilen William Raveis New York LLC
$22,500 per month
935 Southern Cross Rd, Cutchogue, NY 11935
Available 2026: April: $12,000, May: $17,500, June: $22,500, July: $35,000. August Rented. Vacation at this spectacular, completely renovated 4 en suite bedroom home this summer located in the desirable Fleet's Neck neighborhood with 2 gorgeous beaches moments away! Entertain in the open concept living area featuring a large island overlooking the family and dining area, perfect for large
Mariah Mills Daniel Gale Sothebys Intl Rlty
$6,000 per month
1155 Old Harbor Rd, Southold, NY 11971
Quintessential North Fork sandy bay beachfront rental. Stunning views across Cutchogue Harbor and Peconic Bay will be yours at this spacious waterfront home, whether from the airy great room, the brick patio, or from the beachside deck. Tucked away down a quiet drive, this home offers peace and privacy in historic New Suffolk. There are 3 bedrooms and 2 baths upstairs, one bedroom and one bath
Marianne Collins Brown Harris Stevens N Fork
$8,000 per month
400 Wells Rd, Laurel, NY 11948
** RENTED JULY 5th - AUGUST 21st. ** Adorable 3-bed, 2-bath rental with a pool in the fenced in back yard and close to a bay beach! Available Off Season (Jan-May23): $4,000/mo, June: $8,000, July: $9,000, August: $10,000, July & August: $18,000, Memorial Day - Labor Day: $26,000, September (not including LBD): $6,000, October: $6,000, November: $5,000 and December: $5,000. *Unavailable 6/28/26 -
Mariah Mills Daniel Gale Sothebys Intl Rlty
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