Cutchogue, NY Homes for Rent

Renovated Coastal Retreat with En-Suite Baths & Stunning Water Views Experience North Fork bliss in this meticulously renovated beach house located in the heart of Cutchogue. Situated just moments from the highly coveted Nassau Point Beach, this home offers the ultimate blend of modern luxury and seaside serenity. The Interior: Natural light pours into the open-concept living and dining spaces,

William Mcintosh Daniel Gale Sothebys Intl Rlty

Beautiful and classic bungalow style Cottage set on lovely private lot in Fleets Neck beach community with access to the private association bay beach. Featuring 2 bedrooms, renovated bath and kitchen, covered side porch for outdoor dining and spacious rear patio area with fire pit and grill ideal for easy entertaining. Private backyard, outdoor shower. Available July 19 – Aug 2 $5,000; Sept 1 –

Janet Markarian Daniel Gale Sothebys Intl Rlty

A classic North Fork beach cottage in an unbeatable location on West Road in Cutchogue.1240 West Road offers a three-bedroom, one-bath home designed for year-round North Fork living at its best. With access to one of the area’s most beloved bay beaches just across the street and a marina at the corner for boating enthusiasts, the location is truly hard to beat. Whether returning from a day at

Kieran Collings Douglas Elliman Real Estate

Set on .50 acres in the heart of Cutchogue, this newly renovated home offers fresh, modern living with classic North Fork charm. The property has just undergone a full top-to-bottom renovation, giving you the comfort of brand-new systems, updated interiors, and a crisp, clean aesthetic throughout. Featuring light-filled rooms, updated windows, new flooring, and a redesigned kitchen and baths, the

Andrea Parks Douglas Elliman Real Estate

Charming Cape available as year-round rental in beachy neighborhood in the heart of the North Fork. Recently renovated, this 2-bedroom, 1-bath home enjoys a semi-open floor plan and plenty of living space. The attached garage, large basement, and full attic provide ample storage space. Situated just over a half mile from Nassau Point causeway beach. Southold Town Rental Permit # 1397. Expires

Eric Elkin Compass Greater NY LLC

Move-in-ready, furnished year-round rental in the sunniest hamlet of New York—Cutchogue. This cute 3-bedroom, 1-bath home offers comfortable living with a bright, clean interior and a convenient Main Road location close to all the North Fork has to offer. The home comes fully furnished for easy living and immediate occupancy. Garage is not included. Utilities are not included. A great opportunity

Joseph Divello Century 21 Albertson Realty

Cutchogue-Spend summer in this quintessential North Fork cottage. Immaculate, beautifully furnished and well equipped home with everything you need for a comfortable stay. Wonderful location just steps to water access for boating, kayaking, paddle boarding, and fishing. Beaches, shopping, restaurants farm stands, fish market, wineries and breweries just minutes away. Available June and/or July

Amy Kirincic The Agency Northshore NY

SPARKLING BAY FRONT Available MD-LD $140,000Bay front living in prestigious Nassau Point. This spacious, newly renovated home features 4+ bedrooms, large living room with fireplace, eat-in kitchen and an office. 100 feet on the Bay and a full acre, waterside deck overlooking Peconic Bay, steps to private beach, gunite & heated pool, pool house with a kitchenette, recreation area, changing

Sheri Winter Parker Corcoran

Cutchogue, North Fork – Year-Round Designer Home in Arboretum SettingExperience year-round living in this fully furnished designer home, tucked away in a lush, arboretum-like setting in the heart of Cutchogue. Thoughtfully curated and impeccably maintained, this residence offers a seamless blend of style, comfort, and natural beauty. The open-concept floor plan provides expansive living and

Nicholas Planamento William Raveis New York LLC

Cutchogue, North Fork work-live annual rental features 2 plus bedrooms, 2.5 baths and lots of light in contemporary farmhouse style. Previously a retail/commercial art gallery - let you imagination run wild with potential work/live uses. Open floor plan features large living room with decorative wood stove, dining room, eat in kitchen with sitting area and deck access. Bonus room and 2 car garage

Nicholas Planamento William Raveis New York LLC

Bucolic farmhouse on three lush acres in the heart of Cutchogue! This home features two large bedrooms each with queen beds and smaller third bedroom on second floor. There is a sunporch with sleeper sofa that would make an ideal work from home space. Outbuilding/shed on site can be used for storage. Half bathroom is on the first floor and a full bathroom newly tiled on the second floor.

Melissa Principi Douglas Elliman Real Estate

July rental in picturesque beach community. Deeded beach and playground nearby. This 3 bedroom home is fully air conditioned. Has WIFI and an outdoor shower. Additional information: Lease Term:July, Memorial-Labor, September, October, Monthly, Off Season.

Maureen Orientale Compass Greater NY LLC

Available for July 2026 (50K). Escape to this stunning five-bedroom retreat on Nassau Point, offering 150 feet of waterfront access and just a short 3 minute stroll to the pristine sands of Fishermans Beach. This property combines natural beauty and modern luxury.The home features elegant furnishings, modern fixtures and high-end finishes throughout. Outdoor living spaces, including

Natalie Hough Daniel Gale Sothebys Intl Rlty

2026 Rates: June $10K, July $15K, A1-LD $17,500, September $6,500, October $7K Charming Nassau Point Cape Cod. Enjoy sprawling private grounds with community beach access as you enjoy the summer months in this ideal 3 bedroom 2 bathroom escape. The main level features and open dining/, kitchen leading to wood deck, main floor bedroom, full bathroom and living room. The second floor features 2

William Walters Daniel Gale Sothebys Intl Rlty

Escape to your private Cutchogue oasis this summer! This stunning home boasts four bedrooms, including two en-suite, and 3.5 baths, offering luxurious accommodations for your getaway. Unwind in the in-ground pool or lounge on the wrap-around porch overlooking a tranquil creek. Two living rooms and an open-concept kitchen provide ample space for entertaining, while the wooded lot ensures complete

Mackenzie Needham Daniel Gale Sothebys Intl Rlty

Have the best getaway ever in this newly renovated home in prestigious Nassau Point! At its heart is a sunny great room with a soaring cathedral ceiling. The chef’s kitchen includes premium appliances, a large island, and flows into the living room with backyard views. The formal dining room, with bay views, is perfect for more formal gatherings.The main floor features a queen bedroom, a

Diane Arpaia Signature Premier Properties

Don't miss your chance to rent this unparalleled estate, nestled on 5 picturesque acres among the region's most prestigious vineyards.This magnificent home is a perfect blend of elegance and tranquility, ideal for those seeking a refined living experience.Spanning an impressive 7,000 sf, the residence is designed with sharp attention to detail. Floor-to-ceiling windows flood the space with

Lisa Gillooly Compass Greater NY LLC

**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

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

Perfect summer getaway! 3 bedrooms, 2.5 bathrooms, in-ground pool, close to beach, business district, vineyards and restaurants. Two week minimum stay., Additional information: Appearance:very good

Erin Kaelin Signature Premier Properties

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,Off Season,Weekly Rent Amt:2000

Erin Kaelin Signature Premier Properties

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

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

Jeanmarie Bay William Raveis New York LLC

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

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

Available: May $8K; June $15K; July $20K; Aug-LD $25K; Sept $10.5K; Oct $8.5K Romance, elegance, and the bucolic backdrop of Oregon Road make this home a standout! Nestled within a vineyard, this 3 bedroom, 2 bath vintage farmhouse charmer lies on 2 acres with an in-ground pool and endless vineyard views. Short distance to tasting rooms, farm stands, renowned restaurants, vineyards, and fantastic

Sheri Winter Parker Corcoran

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