luxury real estate for rent Cutchogue, United States

Stunning Renovated Craftsman in Nassau Farms – North Fork Summer Retreat- Enjoy the perfect North Fork escape in this pristine, renovated Craftsman home located in desirable Nassau Farms, just moments from Nassau Point Beach. Designed for relaxed summer living, the bright and airy great room features an open-concept layout filled with natural light. The chef’s kitchen is beautifully appointed with granite countertops, custom cabinetry, and high-end appliances — ideal for entertaining family and friends. Lovely Primary en-suite with 2 additional guest bedrooms. Step outside to your private backyard oasis complete with a bluestone patio, built-in outdoor sound system, stone fireplace, and full outdoor cooking area. Whether you’re hosting sunset dinners or enjoying quiet evenings under the stars, this home delivers the ultimate vacation experience. A private path offers easy access to nearby kayaking, and you’re conveniently close to all North Fork attractions including beaches, wineries, farm stands, and charming local shops. Available Summer 2026 -( June – $10K , July – $15K, September – $15K. Off-season rates available upon request. Permit #0283

Available 2025: April: $12,000, May: $17,500, June: $22,500, July: $35,000. 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 gatherings. The first floor features 2 bedrooms with 2 full baths with glass sliders leading out to the deck. Downstairs has 2 more ensuite bedrooms with glass sliders leading out to a patio. Soak up the sun and relax by the saltwater pool, rinse of the sand with the spacious outside shower or enjoy the patio where there is plenty of room to entertain throughout any time of the day.

2026 Rates: 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 additional bedroom and 1 full bathroom. Don't let this amazing East End retreat slip away!

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 Ceilings, Primary Master Suite, 3 Additional Bedrooms, An Eat-In Kitchen And an additional 2.5 Baths. If you're looking for privacy, ideal water access and one of the best location the North Fork has to offer, this is not to be missed!

Escape to the serene charm of New Suffolk this summer with this beautiful rental property! Offering ample space for all, this delightful home boasts 5 bedrooms and 3 bathrooms, ensuring everyone's comfort. Step outside onto the expansive wrap-around patio, perfect for summer evenings and al fresco dining. An outdoor shower provides a refreshing touch after a day at the beach, and the large, lush yard offers plenty of space for recreation and relaxation. Whether you're a culinary enthusiast grilling up a feast or simply enjoying the company of loved ones in the spacious kitchen, this home is designed for entertaining and creating lasting memories. Nestled in the coveted New Suffolk community, you'll be just moments away from the area's most stunning beaches. Embrace the quintessential summer lifestyle in this lovely retreat, where comfort and convenience meet coastal charm.

Summer Rental in New Suffolk! Enjoy summer on the North Fork in this well-appointed New Suffolk rental featuring partial water views, a spacious yard, and easy access to local beaches, dining, wineries, breweries, and farm stands. The home offers flexible living spaces, three bedrooms, two full baths, and multiple indoor and outdoor areas for relaxing and entertaining. Amenities include an eat-in kitchen, dining room, outdoor shower, charcoal grill, fire pit, washer/dryer, dishwasher, parking for four vehicles, and a large yard with outdoor seating. The first-floor layout includes a private bedroom, full bath, and adjoining sunroom, while the second floor offers additional bedrooms, a full bath, and a separate lounge area. Conveniently located near New Suffolk waterfront attractions and just minutes from the many vineyards, restaurants, and recreational opportunities throughout the North Fork. Summer 2026 Availability -June (2 week minimum) - $3000 per week, July and August (2 week minimum) - $4000 per week

2026 Rates: NO AVAILABILITY New Modern Farmhouse Completed in 2021 and located in the heart Hog's Neck in Southold Hamlet. This home features an impressive 20 x 50 heated pool with electric cover, out door shower and sprawling paver patio. The interior is open and airy with Chef's Kitchen outfitted with Thermador appliances, large living room with built in shelving, gas fireplace and formal dining room. All four bedrooms are located on the second level: 1 Primary En-suite, 1 Junior Suite, 2 Guest Bedrooms and Full Hallway Bathroom. You will enjoy being within close proximity to Goose Creek, South Harbor Park Beach and Southold's vibrant business district!

Impressive Goose Creek home with water views and large heated in-ground pool! This four bedroom, three bath house features a first floor primary bedroom with en-suite, a gourmet kitchen and open living space. The newly designed landscape with outdoor kitchen (not pictured) is ideal for entertaining or relaxing. Enjoy its large fire pit and BBQ grill after an afternoon of Kayaking. Close to Southold town and Corey Creek Beach. 2026 Pricing: July $30K | Aug-LD $35K

Offered as a Year Round Rental (NO PETS)! Welcome to 435 Lupton Point Road, a beautifully appointed coastal residence tucked within a private Mattituck waterfront community offering direct water access to Deep Hole Creek and a private dock. Spanning approximately 2,700 square feet, this thoughtfully designed home features a spacious open floor plan ideal for both everyday living and entertaining. At the heart of the home is a chef’s kitchen, complete with generous counter space and seamless flow into the dining and living areas. A wood-burning fireplace anchors the living room, creating a warm and inviting atmosphere year-round. The home offers four well-proportioned bedrooms, two and a half bathrooms, and a dedicated home office, providing flexibility for remote work or guests. Natural light fills the interiors, enhancing the home’s airy coastal feel. Step outside and enjoy the rare convenience of water access with a private dock, perfect for boating, kayaking, or simply enjoying the peaceful creekside setting. The property’s location offers the best of North Fork living—just minutes from Love Lane’s shops, cafes, and farm stands, as well as New Suffolk Beach, making it an ideal full-time residence or weekend retreat. A unique opportunity to enjoy privacy, water access, and timeless North Fork charm in one exceptional offering. NO PETS

Offered June $10,000 ($2,500/wk); July $20,000 ($5,000/wk); Aug $25,000 ($6,250/wk); Sept $12,000 ($3,000/wk); Oct $10,000 ($2,500/wk). Two-week minimum. This contemporary waterfront home on Great Pond enjoys sunrise over the water and spectacular sunsets over Long Island Sound from its hilltop setting in one of the North Fork’s most distinctive beach communities. Surrounded by native plantings and filled with natural light and cooling breezes, the home is designed for effortless indoor-outdoor living. Spanning three floors and 2,600 square feet, it features 3 bedrooms, 4 full baths, and multiple spaces for gathering, entertaining, or quiet retreat. Enter from the spacious front deck, with seating for four and views of lush natural landscape and Sound. The main level comprises an open-plan living room with a wood-burning fireplace, dining area, eat-in kitchen, TV room, full bath, and a rear deck with dining table for six overlooking Great Pond. The ever-changing landscape of water, sky, and birdlife makes this a haven for nature lovers. Upstairs are two ensuite bedrooms, both enjoying beautiful water views and brand-new bathrooms, the one in the master suite benefiting as well from a long bathtub. The garden level offers a third bedroom, full bath, laundry area, movie and screening room, and an office/den with glass doors opening onto a rear deck with lounge chair, sauna, and outdoor shower. A private path leads directly to Great Pond, where kayaks and a canoe await exploration. Additional amenities include bicycles, a massage chair, piano, binoculars, telescope, and EV charger. Kenney’s Beach and the beloved Little Fish restaurant are just a short bike ride away, creating an exceptional blend of comfort, privacy, and outdoor adventure in the heart of the North Fork.

Summer is here, and this home has vacation written all over it. Enjoy spectacular sunset water views of the Long Island Sound from the spacious wrap-around deck or from the bright, open-concept living spaces inside. Perfect for entertaining, the layout features 4 bedrooms and 2 full bathrooms, offering a beautiful oasis for relaxation and togetherness. The lifestyle here is effortless: Kenny's Beach access is just steps away (.02 miles) for swimming in the Sound, complemented by a refreshing outdoor shower back at the house. Plus, you can leave the car behind and stroll down the road (.03 miles) to grab lunch or dinner at the hot new local restaurant, Little Fish. Let's get you set up in the perfect summer getaway—inquire today! Availability: June 15-June 30th $10K | July $35K | August $30K

Two week minimum rental. Available in July and August, $4,500 / week. August 16 through Labor Day, $5,500/week. 3% discount for rentals longer than 3 weeks. Perfectly situated in one of the North Fork's most desirable beach communities, this welcoming 4-bedroom, 2-bath, 2-story beach bungalow is just a 3 minute stroll to the sandy shoreline of Kenney's Beach, 7 minutes to the Great Pond, a 10 minute walk to McCabe’s beach and a 2 minute walk over to Little Fish restaurant. Oozing vintage beach-house charm, this gem makes for the perfect seaside getaway with family or friends where you can park your car and leave the city behind. What makes the house special is being surrounded by sandy outdoor space, the comfortable gathering spaces for family and friends, anchored by two levels of patio, an outside fire pit on the sand, and an indoor wood-burning fireplace for cooler evenings. It feels like your own private beach oasis and a private after-hours evening at the beach. The spacious main-level deck is ideal for al fresco dining after a day at the beach, and a private second-floor deck off one of the bedrooms where you can enjoy evening sunsets, and views toward Long Island Sound. Fire up the new grill after a day by the water, unwind with a good book on the deck, or grab the provided beach chairs and umbrella and stroll to Kenney's Beach for swimming, beachcombing, or simply watching the sunset. Beyond the neighborhood, discover the very best of the North Fork, from award-winning wineries and farm stands to waterfront restaurants, galleries, boutiques, and charming village centers. Other nearby favorites are Horton Point Lighthouse, a beach stroll that connects the coast from Horton’s Lane (one of the most picturesque inlets) to MacCabe’s and Kenny’s Beach (40 minute walk), easy hiking and walking trails at Goldsmith Inlet Park, and Little Ram Oysters farm stand. Close proximity to Greenport, East Marion and Southold. Whether you're planning a family vacation or a getaway with friends, this inviting Southold retreat offers the perfect combination of beach bungalow charm, comfort, convenience, walkability and the effortless coastal lifestyle that makes the North Fork such a special destination.

2026 Rates: September $7500; October $10,000: Discover your perfect getaway in this expansive and meticulously updated ranch home, designed for relaxation and rejuvenation. Experience a resort-like atmosphere with the stunning gunite, heated saltwater pool, complemented by a beautiful stone surround and convenient outdoor shower. Step inside to find high vaulted ceilings that create an airy ambiance and an abundance of natural light. The home boasts stunning hardwood floors and is elegantly appointed with multiple living areas that provide the perfect balance of open space and private retreats. Ideally situated within walking distance of Kenney’s Beach, you’ll find yourself just moments away from charming local cafes, unique boutiques, renowned wineries, and exceptional dining options. This North Fork gem is truly the ultimate summer haven. Don’t miss your chance to experience the perfect blend of comfort and convenience!

** 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 - 7/4/26.

Escape to the heart of the North Fork in this beautiful, spacious four-bedroom home, perfectly designed for entertaining and hosting. Inside, you'll find ample living space complemented by a fully finished basement—ideal for extra lounging or movie nights—while the private backyard oasis features a sparkling heated pool for endless summer fun. Centrally located just one mile from Breakwater Beach, this home offers unbeatable access to the very best of the region, putting you just minutes away from the charming shops on Love Lane, premier local vineyards, and acclaimed farm-to-table restaurants. Book your stay today and secure the perfect central base for your ultimate retreat!

Fabulous, like new modern home available for rent. Serene water views from living areas, deck and gunite, in-ground, heated swimming pool. A short 300' to the sandy bay beach. The home was completely renovated in 2020. The home offers open concept living at its best with wall to ceiling glass doors letting the outdoors in and offering serene water views. The first floor also offers a separate den that can also be used for an additional bedroom. There is a guest bedroom with full bath on the first floor. The second floor has 2 additional en-suite bedrooms (including the large primary suite with a sumptuous bathroom) and a sun filled landing designed for relaxing and play. This home is a perfect vacation home offering all modern amenities, a swimming pool, water views with access to a sandy bay beach. [[Rental Registration # RP220388]] EH RR #: RP220388 Rental Terms: July: $59,000 March: $10,000 June: $29,000 Memorial Day - Labor Day: $129,000 January: $10,000 September: $20,000 May: $12,000 February: $10,000 October: $15,000 August - Labor Day: $65,000 July - Labor Day: $115,000 November: $15,000 August: $59,000 April: $12,000 Winter Season: $50,000 Per Month Other / Short Term - Dec: $15,000

This Southampton beach house blends playful coastal personality with relaxed Hamptons living. Located in Bay View Oaks, a waterfront community with private beach access, deeded rights to Peconic Bay, and a boat launch, the home sits in a quiet setting within Bay View Oaks, just 10 minutes from both Sag Harbor and Southampton Villages. Inside, the home features high ceilings, light-filled rooms, and professionally designed interiors with a cool design sensibility that incorporates open-plan living, retro pop-culture touches, and colorful accents. The layout includes four bedrooms plus a bonus bunk room, 3.5 bathrooms including a primary ensuite, and multiple indoor-outdoor gathering zones that flow naturally for lounging, dining, and entertaining. A gourmet kitchen inside and out, multiple dining areas, and a layout arranged for smooth day-to-day living make the home easy to enjoy. The outdoor spaces offer a range of playful amenities. After the beach, rinse off sandy toes in the outdoor shower, step into the heated pool, basketball hoop, trampoline, fire pit, and several lounge areas suited for relaxing or gathering. A two-car garage and the overall setting bring everything together for a relaxed Hamptons stay. Offered for the early summer, August, extended season, and winter rental periods. [[Rental Registration # RP241487]] EH RR #: RP241487 Rental Terms: July: $50,000 June: $38,000 August: $55,000 October: $12,500 November: $10,000 Winter Season: $50,000 Per Month

Welcome to 4 Scrimshaw Drive, located in the sought-after Whalebone Landing community, where summer feels calm, private, and effortlessly beautiful. Enjoy the private bay beach and tennis courts just moments away, and quick access to the boutiques, restaurants, and harbors of both Southampton and Sag Harbor. Designed for luxury summer living, this home features a heated gunite pool, sun-filled interiors, and three levels of finished living space ideal for both relaxation and entertaining. Coastal-inspired details throughout the home create a natural sense of ease and timeless Hamptons elegance. With convenient proximity to the U.S. Open PGA at Shinnecock Hills Golf Club in June 2026, this residence offers a refined retreat for those seeking to experience the very best of the Hamptons with style, privacy, and comfort.

Tucked away in the sought-after Northside Hills community, this beautifully appointed five-bedroom rental blends classic Hamptons charm with modern comforts. Ideally located just minutes from Sag Harbor Village, bay beaches, and golf courses, it offers a perfect balance of tranquility and convenience. The spacious living room with a cozy fireplace and formal dining room create an inviting setting for entertaining. A chef's kitchen is outfitted with stainless steel appliances, quartz countertops, a breakfast bar, and a sunny eat-in nook-thoughtfully designed for both style and function. On the main floor, a versatile office/den can easily convert to bonus bedroom with pull-out couch. Upstairs, the designer primary suite features an en-suite bath, joined by four additional guest bedrooms and two separate full baths. One of the bedrooms includes an adjacent bonus living area with television and Peloton, ideal for relaxing or keeping active. Outdoors, enjoy a spacious backyard and deck for al fresco dining, plus a heated pool for leisurely afternoons. This is the perfect summer rental for relaxation and refined Hamptons living. #RP260016 [[Rental Registration # RP260016]] EH RR #: RP260016 Rental Terms: Two Weeks: $25,000

Also Available: May 23rd - Jun 30th $35K, Jan 1st - May 23rd 35K A gated, private entrance leads to this well-appointed 5 bedroom home with 2 primary suites. The home is set on a gorgeous 1.3 acre property, with grounds that impress all. A fully renovated, newly furnished interior features a double height living room with fireplace, open kitchen, dining room with private courtyard and new gym! One of the two primary suites is on the first floor. There is a second primary with large balcony upstairs, plus 2 additional generous bedrooms. Conducive for working or learning from home, the owners built out an office and reading nooks and detailed carpentry. A newly finished lower level has a TV room with large screen TV and 5th bedroom. An attached garage with bikes is an added bonus for exploring this quiet neighborhood. Completing the estate-like setting, there is over 2000 square feet of decking and an impressive Tortorella-designed gunite pool with waterfall. Located in prestigious Northside Hills, within the coveted Sag Harbor School district. [[Rental Registration # RP231033 - 10/03/2025]] EH RR #: RP231033 Rental Terms: August - Labor Day: $65,000 November: $9,000 June: $35,000 July: $60,000 October: $10,000 August: $60,000 Memorial Day - Labor Day: $150,000 July - Labor Day: $125,000 April: $10,000 September/October: $27,500 March: $9,000 May: $15,000 January: $9,000 Other / Short Term - Year Round: $165,000 February: $9,000

Available for rent, this newly renovated Sag Harbor estate blends modern sophistication with laid-back coastal charm-perfect for a luxurious Hamptons escape. Fully gut-renovated and thoughtfully expanded, the 2,680 sq. ft. home features brand-new hardwood oak floors, Restoration Hardware finishes, a built-in sound system, and an abundance of natural light. The main living room boasts soaring ceilings, a custom bar, and seamless flow into the open-concept kitchen outfitted with top-of-the-line WOLF, Sub-Zero, and Miele appliances. With five bedrooms and four-and-a-half spa-like baths, the home comfortably accommodates guests, including two separate master suites with ensuite baths, soaking tubs, and walk-in showers. A flexible nursery space can serve as an office or dressing room, and a second private office at the entrance is ideal for remote work. Outside, enjoy a south-facing 0.58-acre property with a heated gunite pool, sun-drenched deck, lounge and dining areas, and lush landscaping. The home also includes solar panels, an electric car charger, a full laundry room, and deeded beach rights-perfect for launching kayaks or paddleboards. Just a mile from Long Beach and moments from Morton Wildlife Refuge and Noyac Golf Course, this rental offers the ultimate in Hamptons living. [[Rental Registration # RP251335]] EH RR #: RP251335 Rental Terms: September: $35,000 October: $20,000 November: $15,000 Two Weeks: $17,000 Other / Short Term - Dec: $15,000

Privately situated on one +/- acre in Northside Hills, this newly renovated, designer's own home boast every amenity. The chef's kitchen includes all stainless steel appliances, custom cabinetry, stone back splash, granite counter tops, and center island with built in wine cooler. Graciously opening up to dining room, great room with fireplace and living room makes for seamless entertaining. The first floor also includes a large guest suite with private bath. Second level features three bedrooms; two master suites, both with walk in closets, extra large spa baths & fireplace. Enjoy summers with free form, infinity edge heated gunite pool or lounge outside on your mahogany wraparound porch for quiet enjoyment. The finished lower level serves as a game room and tv room with plenty of extra storage. This beautiful homes is minutes from three great villages: Sag Harbor, Bridgehampton & Southampton making it an ideal rental! Dec - April $6,800 per month [[Rental Registration # waitingforrp]] EH RR #: waiting for rp Rental Terms: July - Labor Day: $155,000 May: $28,000 June: $35,000 October: $16,000 September: $30,000 Other / Short Term - Year Round: $280,000 August - Labor Day: $78,000 Memorial Day - Labor Day: $180,000 July: $78,000

Nestled on a quiet cul-de-sac among expansive three-acre estates, this beautifully landscaped Hamptons retreat offers the perfect blend of privacy, recreation, and convenience. Backing directly to Noyac Golf Club and surrounded by more than 135 acres of scenic hiking and jogging trails, the property is an ideal escape for summer living. Designed for effortless indoor-outdoor entertaining, the home features a dramatic double-height living room, a newly renovated kitchen, and a spacious dining room with seating for 12. A wall of sliding glass doors fills the home with natural light and opens to the expansive patio, heated gunite pool, and Har-Tru tennis court. The thoughtfully designed layout includes six bedrooms and six bathrooms, all above ground, with two en-suite guest bedrooms conveniently located on the first floor and a spacious primary suite upstairs, along with three additional guest bedrooms. Furnished with two king beds and five queen beds, the home comfortably accommodates up to 14 guests. Ideally situated just minutes from Towd Point Beach, Long Beach, marinas, and several popular waterfront restaurants, and only 12 minutes from the villages of Southampton, Bridgehampton, and Sag Harbor, this exceptional property offers easy access to the very best of the Hamptons while providing a peaceful country setting. Rental Registration #RP160829. [[Rental Registration # RP160829]] EH RR #: RP160829 Rental Terms: July: $70,000 August - Labor Day: $70,000 July - Labor Day: $140,000

WATERFRONT COMPOUND WITH POOL! Swim, fish, or launch the kayak, paddle board or sunfish sailboat(included) from this waterside haven! Located on Davis Creek, this Towd Point Beach Rental has unobstructed views of the harbor and beyond to Conscience Point National Wildlife Refuge. Featuring a cottage-style main house with three bedrooms and two bathrooms and a modern-barn style pool house that takes full advantage of the stunning views. The two-story pool house has two full bathrooms, a wet bar, an outdoor kitchen, and seating areas on both levels with sliding doors that bring the outside in - it's where you'll be hanging out. The main house also has outdoor dining, incredible views and an outdoor shower. The heated, salt-water gunite pool is NEW FOR SUMMER 2024 and includes an endless swim current for lap swimmers. Moments to the beautiful Towd Point Beach. [[Rental Registration # rp250468]] EH RR #: rp250468 Rental Terms: July: $85,000 Memorial Day - Labor Day: $220,000 June: $50,000 August: $85,000 November: $20,000 August - Labor Day: $90,000 October: $30,000