33 houses for rent in Cutchogue

Also available for the custom dates: September 1 - 7: $125,000 September 8-31: $50,000 per week This is not a home, it’s a LIFESTYLE RESORT, a HOUSTEL called WILLIEVILLE. If you enjoy entertaining, then this home is for you. Everything you can imagine is perfectly set up—no detail has been overlooked, including THE FORCYNTHIA VINEYARD EXPERIENCE, where a full case of private reserve Rosé is included each week. This 8 bedroom, 9.5-bath, industrial modern barn built and designed by celebrity lifestyle restaurateur William Jack Degel, is located on 1.83 acres in Watermill's pristine horse country. The outdoor oasis features a 2,000 square feet covered outdoor living space with a full kitchen, fridge, pantry, bar, lounge, fireplace, dining area, 85 inch TVs, infrared heaters, and a covered raised 12 person heated spa. The private vineyard in the back drop named FORCYNTHIA, showcases Wolffer grapes and picnic tables. Adjacent is the 50-foot gunite saltwater pool, 10 by 10 raised spa, a sun

This perfectly located Sag Harbor Village waterfront home with a private dock is ready for your enjoyment! Situated on the storied and private Bluff Point Lane, this home offers unmatched tranquility and generous views of Upper Sag Harbor Cove! This special home boasts three bedrooms, one and a half baths, an inviting living room with a fireplace, dining table overlooking the water, ample decking to enjoy spectacular sunrises and sunsets, outdoor shower and so much more! This is a must see! Available 10/1/2026 - 4/30/2027 $6k/month

Available for 2026 US Open for $100,000 This incredible modern-traditional 7 Bedroom, 7.5 Bath home features 8457+/- sqft of living space including extensive ground level and 1st floor deck. Completed in 2021, the new construction is situated on a very private 2.80 +/- acres in beautiful and convenient Water Mill. A covered front porch provides access to a grand double height foyer with great room and upper deck. The formal dining room in the front of the building connects the large gourmet chef's kitchen with breakfast room and butlers pantry with wine fridge. The great room and separate living room share a beautiful double exposure fireplace and a huge junior primary bedroom with walk-in closet features a private bath with double sinks. Upstairs, an impressive master suite has a grand bath with soaking tub, two walk-in closets and a separate linen closet. Three additional guest bedrooms each with en-suite baths are also located on this level with a convenient double capacity laundry

Located on Morris Cove in Sag Harbor Village, is this spectacular five bedroom, newly renovated and furnished, waterfront home! Relax on the deck and take in the tremendous sunsets over the water, take your boat for a spin, or head to Main Street for fine dining. The first floor features three bedrooms and one and a half baths, an updated kitchen, dining room and living room with spectacular water views. The walkout lower level is setup as its own separate apartment and features two more bedrooms and a full bath with a kitchenette, additional living space and sliders to the backyard and dock. There is no better place to spend your summer in Sag Harbor than at 11 Bluff Point Rd!

This amazing new construction 6400 sq ft home exudes luxurious modern living with all the latest smart home wiring devices. Perfectly positioned, facing southwest the home is drenched with unrelenting natural light, all day. This expansive, open-concept home offers a gourmet chef's kitchen, island seating, breakfast area, formal dining room, and a considerable living/family room with sliding glass doors that open up to the beautifully landscaped backyard, inground gunite 20x40ft pool, and conveniently designed patio creating a private oasis or the perfect space to entertain. The generous master suite is fully equipped with a walk-in closet and custom shelving. Five additional spacious bedrooms, five full bathrooms and two half bathrooms. The lower level is fully finished with media room, exercise room with sauna, and additional storage areas. Virtual Tour

This inviting 4-bedroom, 3+ bathroom home is situated on nearly an acre of land. On the first floor, you'll find a newly renovated kitchen (completed in winter 2024), a cozy sitting/living area, a dining room, and a bonus room that could be used as an office or flex space. Upstairs, the primary bedroom is accompanied by three guest bedrooms. A finished lower level with bonus room gives plenty of indoor living space for extra guests that stop by. The backyard oasis is a relaxing retreat with a heated pool, full bar area with kitchen space and multiple lounge areas to enjoy the hamptons summer sun! This home has all the amenities for the most amazing summer you have had yet!

Located in the coveted Southampton shores community this five bedroom, two bathroom has all you need for a summer getaway. Location can't be beat as this is the second home from the entrance of the private community beach and just up the road from the community tennis and basket ball courts. This home features three bedrooms on the second floor with full bath and two additional guest bedrooms and full bathroom on the first floor. Lots of privacy for all with this home and don't forget to enjoy your time on the large back deck perfect for summer night bbqs. Call today for more information

Light-filled, beautifully renovated and updated four bedroom, two and a half bath home on a just-shy half acre in Shinnecock Hills isstylish and flooded with natural light. Open upstairs living areas feature a wall of energy-efficient glass doors opening to an upperdeck, and flow among a living area, formal dining area and beautiful kitchen with new cabinets, granite countertops and stainlesssteel appliances. All new baths feature marble flooring and walls, and new fixtures. Additional upgrades include new hardwoodflooring on the upper level, updated electrical work, new front roof, all new paint, new A/C and heating system, smart wiring for Sonos, high speed internet and cable lines. Extensive decking surrounds the heated pool wonderful gardens. Making this such a sought after location as you have Meschutt bay beach and Coopers ocean beach, which offers daily parking, all within 10 minutes. Available one week of US OPEN at 9k plus expenses

Ideally located between Southampton Village and Hampton Bays, this south-facing Shinnecock Hills ranch is the perfect summer escape. Set on.60 acre on a quiet street, the home offers simple, comfortable living with easy access to both ocean and bay beaches. With three bedrooms and two full bathrooms, there’s plenty of space to relax and unwind. The bright and open gathering/dining room is the heart of the home, featuring vaulted ceilings with wood beam detail, a wood-burning fireplace, and sliding doors that lead out to a large deck and private backyard—ideal for summer lounging and entertaining. The kitchen is well-equipped with stainless steel appliances and granite countertops, making at-home meals a breeze. A new composite deck with sleek post-and-wire railings adds to the home’s relaxed, stylish feel. Whether you're spending the season exploring the Hamptons or just unwinding close to the coast, this charming home has everything you need for an effortless summer

This 3 bedroom, 1 bath home is nestled right out side of sag habor village. Less than 1 mile from long beach as well as Sag Harbor Village this home is an easy getaway to paradise. The home was just lovingly refreshed and renovated so there is nothing to worry about with your rental. Brand new chefs kitchen, along with wine fridge opens up to in kitchen dinning and over looks the living area. The backyard is perfect for grilling out and enjoy the summer nights. Call today to make this rental your summer getaway

Southampton Beach House | Heated Pool, Bay Views & Prime Southampton Location Enjoy the ultimate Hamptons escape in this beautifully appointed 3-bedroom, 2-bath home, ideally situated across from Shinnecock Bay and just minutes from Southampton's renowned beaches, golf courses, waterfront restaurants, and village shopping. Accommodating up to 7 guests, this turnkey retreat offers the perfect balance of comfort, style, and outdoor living. Property Highlights: •3 Bedrooms | 2 Bathrooms | Sleeps 7 •Heated pool with all-day sun exposure •Private backyard oasis •Multiple outdoor decks for entertainment and relaxation •Expansive front and back lawns •Open-concept kitchen and living area •Primary suite with ensuite bath •Large den/playroom with additional sleeping space •Central air conditioning •Solar-heated pool for energy-efficient enjoyment •Ideal setup for remote work and extended stays Step outside and embrace the Hamptons lifestyle. The private backyard is designed for summer living, f

Step into a realm of pure Resort Style living and waterfront splendor within this newly designed Hamptons Bayfront masterpiece. Behind the estate gate, graciously situated on a serene and meticulously maintained 1.4 acres, ensconced by vibrant gardens and exquisite specimen plantings, this distinguished Bayfront residence finds its place along the illustrious Dune Road. Here, where luxury living meets the tranquil embrace of nature, a sanctuary of waterfront opulence awaits your discovery. Perfectly situated alongside the shimmering bay, with the prestigious Quogue Field Club and golf course views as a backdrop, this unique Hamptons residence not only offers the utmost privacy but also presents a front-row seat to captivating sunsets while playing host to numerous summer activities. The poolside deck and lounge unveil a personal theater for nature's nightly spectacle-a symphony of colors gracefully dancing across the Hamptons skyline. Sitting bayside and center stage is the heated Guni

Tucked away on a private, quiet cul-de-sac south of the highway, this pristine, professionally staged residence offers the ultimate in luxury living—perfect for a summer escape or year-round enjoyment. Boasting 5 oversized en-suite bedrooms and 6.5 baths, this home is masterfully designed with double-height ceilings, an open-concept layout, and an abundance of natural light throughout. The gourmet kitchen is a chef’s dream, outfitted with top-of-the-line appliances, seamless flow into a beautifully decorated dining room, and ideal for entertaining. Enjoy cozy evenings in the spacious living room with a fireplace and flat-screen TV, or relax in the sun-filled great room, also featuring a large TV and elegant decor. The first-floor primary suite offers a spa-like retreat with an en-suite bath, while a second primary bedroom upstairs provides additional flexibility and privacy. Three more grandly scaled guest bedrooms, all with luxurious furnishings and high-end bedding, include dedicated

This Shinnecock Canal front 3 + home, 2+ bath home, built in 2014 is the perfect for anyone who has always wanted to experience waterfront living. New construction, nicely furnished, and minutes to Meschutt Beach, Southampton & Hampton Bays village and ocean beaches. Available until June 21st and can be rented for the US OPEN

This charming three bedroom and two and a half bath home is perfect summer get away. Nestled in North Haven shores beach front community you are steps away from your own private beach and kayak launch point. The first floor features living, dinning, kitchen, den along with laundry and half bath. The second floor features one primary with ensuite bathroom, and two guest bedrooms with shared bathroom. The backyard is the gem of the property with expansive landscaping, outdoor dinning, outdoor shower and fire pit. There is also a beautiful screen-in porch and patio. 10 minutes to Sag Harbor Village with its wonderful restaurants, shopping, world renown Baystreet Theatre and newly rebuilt Sag Harbor Cinema

Modern Bayside Masterpiece with Rooftop Oasis in Southampton. Ideally located within seconds of the world renowned Shinnecock Hills Golf Club, this one-of-a-kind, newly constructed four-level modern residence delivers the ultimate Resort-Style living experience in the Hamptons. Perfectly suited to capture panoramic views of the open waters of Shinnecock Bay, and Atlantic Ocean, this striking Modern contemporary home is a rare offering that blends cutting-edge design with luxurious amenities. Spanning four expansive levels of indoor and outdoor living, the home features 4 spacious ensuite bedrooms and 4.5 bathrooms, each meticulously designed with modern finishes, abundant natural light, and spa-inspired details. The open-concept main level offers seamless flow between the state-of-the-art chef's kitchen, indoor and outdoor dining areas, and an elegant living room that opens to bayfront terraces through floor-to-ceiling glass doors. An entertainer's dream, the fourth-level rooftop deck

Enjoy this newly renovated Southampton Village home with 5 bedrooms and 7.5 baths which boasts 5,300 sq. ft. and features all new high-end staged furnishings and accessories that encompasses everything needed to enjoy a spectacular summer. Included in this full open concept design are beautiful wide plank oak flooring throughout. Upon entering the grand foyer enjoy views of the art work and stunning chandeliers that stretch throughout the home to the yard. There is a separate Home office/Den offering full privacy to use for entertaining or for conducting business with a wet bar and wine cooler in the neighboring hall way. The gourmet kitchen is fully equipped with custom cabinetry, stainless steel appliances including double Miele dishwashers and a marble center island for gatherings, and serves the sun bathed breakfast room. Dine in the grand sun filled great room with spectacular ship-lap 20' ceilings with French doors leading to the serene views of the pool and yard. This integrated

This beautifully restored historic 3-bedroom Victorian blends timeless charm with modernist sophistication, nestled in the very center of Bridgehampton’s coveted hamlet. Every detail of this spacious residence has been sensitively renovated to reflect a high standard of design and comfort, combining original character with sleek, contemporary updates. The main floor features a sunlit living room, a windowed dining area, and a stylish kitchen outfitted with brand-new appliances. A full bathroom and a delightful sunroom—perfect as a home office, library, or serene summer retreat—complete the first level. Upstairs, three bright bedrooms share a renovated full bath. The generous king-sized primary bedroom includes an adjoining ensuite bathroom. Outdoors, enjoy coffee or evening rosé on the inviting front porch overlooking a lush garden, or entertain in the elegant gravel patio surrounded by manicured hedges—an ideal summer setting. Just one block to Bridgehampton’s shops, art galleries, s

Located on one of the most beautiful and desirable streets in Southampton Village, this stunning six-bedroom, six-and-a-half-bath Traditional home is the perfect Hamptons summer retreat. Set on a quiet cul-de-sac east of Lake Agawam and just minutes from Main Street and Little Plains Beach, this estate-like property offers privacy, luxury, and impeccable design. The dramatic double-height paneled foyer welcomes you into a thoughtfully designed home with an effortless indoor-outdoor flow. The main level features a formal sitting room with a fireplace, a gracious dining room with bay windows, and a professional-grade chef’s kitchen that adjoins the open-concept living room with another fireplace. French doors from both the formal and casual living spaces lead to a spacious covered porch with a fireplace, overlooking the lushly landscaped grounds, heated 16’x32’ Gunite pool, and exquisite pool house. Upstairs, the luxurious primary suite is a true sanctuary, featuring a fireplace, walk-in

Completely renovated beach cottage with beautiful views overlooking Shinnecock Bay and with private deeded beach! Ideal for entertaining all summer long with multiple entertaining spaces, 4 bedrooms, large open sunroom and its wonderful roof deck spaces offering endless bay views. Whether relaxing poolside from your saltwater heated pool or from your deeded private beach this ideal Hamptons summer getaway is ready and awaiting your arrival!

Step into your dream Hamptons waterfront summer getaway—truly a paradise for boating enthusiasts. This stunning property offers 4 spacious bedrooms, 3.5 elegant bathrooms, a sleek granite kitchen with top-of-the-line stainless steel appliances, a cozy wood-burning fireplace, and a one-car garage. Designed with entertaining in mind, the open-concept layout flows seamlessly between the living spaces, including a charming screened-in porch—perfect for hosting gatherings or enjoying quiet moments with loved ones. With large windows and expansive outdoor areas, the breathtaking views of Tiana Bay are always within reach. Outside, you’ll find 132 feet of navy bulkhead, ready for your next adventure, offering direct access to the open waters of Shinnecock Bay and beyond—ideal for all your boating and water activities. This Hamptons gem is a peaceful retreat, offering a luxurious escape from the everyday hustle. Don’t miss out on the best deal on the water in the Hamptons this summer!

Enjoy this meticulously maintained light filled Traditional Cape. The open floor plan features 4 bedrooms, 2 full bathrooms, central air, and a casual living room with a smart TV, dining area with doors leading to an attractive landscaped yard perfect for entertaining and quiet evenings. A welcoming kitchen with a large eat in counter bar which features everything you need and is fully equipped. If your a player, a sponsor or a fan, this home offers the ideal location for your US Open experience with easy access to fine dining, ocean beaches, shopping and the Train Station and Gabreski Airport. This is a must see!

Tucked away amid the dunes of Southampton's coveted Oceanfront district of Meadow Lane awaits a traditional cedar-shake Cottage. Perched upon a privately landscaped 1.75-acre parcel that comprises 125 +/- ft of direct Oceanfront. A spellbinding atmosphere defines this seaside enclave; the location allows for captivating vistas of the coastline's sandy beaches and a sense of privacy and seclusion, an ever-rare commodity. Abundant foliage instills an opulent quality into the property's tiered outdoor grounds, which feature a heated saltwater pool, spa, and pool cabana, along with a mixed media tennis court, multilevel decking overlooking the Atlantic Ocean, and a private walkway over the dunes. This Meadow Lane home makes no concessions when it comes to indulgence. Prime location along Meadow Lane allows for convenient access to Main Street and Jobs Lane and surrounding Beach and Tennis clubs, while the heliport awaits one (1) +/- mile(s) away down Meadow Lane. 50 AMP outlet for electric

Come and enjoy your summer in this recently refreshed, 4 bed, 4 bath, 3,000 + square foot home! The first floor boasts a large living room with wood burning fireplace, formal dining room, eat in kitchen with stainless appliances, laundry, two car garage and a full bath. Upstairs you will find two graciously sized ensuite primary bedrooms as well as two additional guest bedrooms and a full bath. The exterior of the home features a brand new heated pool and ample refinished mahogany decking to enjoy on warm summer nights. The lower level provides ping pong, darts and foosball. Bay access at Squires Beach is less than a mile away and ocean beaches are less than a 12 minute drive. Make your appointment to view this wonderful property!

Situated on a full acre in a coveted Bridgehampton South location, this light-filled beach home is just a few lots from the ocean. The living room boasts soaring double-height ceilings and a dramatic wall of windows, showcasing sweeping views of the pristine grounds and capturing the stunning western light. The home features three bedrooms, including a primary suite with views of Mecox Bay, three full baths, a versatile loft space, and an open chef’s kitchen. Expansive multi-level decking and a covered outdoor dining area create the perfect setting for entertaining and enjoying the refreshing ocean breeze. Exceptional amenities include a spacious pool house with a bathroom and outdoor shower, a 50-foot heated gunite pool, and a two-car garage. Surrounded by lush, mature landscaping that ensures total privacy, this property also offers ample room for future expansion

Summer Holiday in the Hamptons! This bright and airy modern contemporary home is the perfect summer retreat—designed for effortless relaxation, entertaining, and enjoying the best of the Hamptons. The spacious great room, with its soaring ceilings, abundant natural light, and cozy wood-burning fireplace, flows seamlessly into the dining area, kitchen with breakfast nook, and multiple outdoor entertaining spaces. Come experience easy living in a summer getaway that truly embraces the Hamptons lifestyle. With four generously sized bedrooms and 3.5 baths, there’s plenty of room for family and friends. The private second-floor primary suite boasts its own fireplace, an oversized bath, and a private balcony—an ideal spot to take in the expansive lawn and breathtaking westerly sunsets.Step outside to your own private outdoor oasis, where tranquility and relaxation await each day. The heated, sun-drenched pool takes center stage beside a brand-new pool house and pavilion, fully equipped for o

Lovely private getaway home in sought after Whalebone Community in North Sea with private tennis, pool, and community bay beach and additional tennis. Bright and airy first floor with large living, dining and updated kitchen which looks out over the pool and tennis court. Two spacious guest bedrooms which share a recently updated bath finish out the first floor. The second floor offers a beautiful lofted living space along with a huge master bedroom with its own private master bath and balcony. This lovely rental is centrally located between Southampton, Bridgehampton, Sag Harbor and to all the Hamptons have to offer

Modern Bayside Masterpiece with Rooftop Oasis in Southampton. Ideally located within seconds of the world renowned Shinnecock Hills Golf Club, a one-of-a-kind, newly constructed four-level modern residence designed to deliver the ultimate resort-style living experience in Southampton. Perfectly suited to capture panoramic views of the open waters of Shinnecock Bay, this striking Modern contemporary home is a rare offering that blends cutting-edge design with luxurious amenities. Spanning four expansive levels of indoor and outdoor living, the home features 4 spacious en-suite bedrooms and 4.5 bathrooms, each meticulously designed with modern finishes, abundant natural light, and spa-inspired details. The open-concept main level offers seamless flow between the state-of-the-art chef's kitchen, indoor and outdoor dining areas, and an elegant living room that opens to bayfront terraces through floor-to-ceiling glass doors. An entertainers dream, the fourth-level rooftop deck is an extreme

Nestled in the heart of Southampton Village, 175 Bishops Lane is the epitome of modern elegance and timeless charm. This newly renovated traditional home offers a perfect blend of luxurious living and serene escape. Spanning 5,647 square feet over three levels, the property boasts 7 spacious bedrooms and 6.5 beautifully designed baths, providing ample room for family and guests alike. Upon entry, you are welcomed by a stunning double-height foyer, setting the tone for the grandeur and warmth that lies within. The versatile layout of the home allows for the option to convert two of the bedrooms into a state-of-the-art movie theater and gym, transforming the space into your own personal retreat. A thoughtfully designed mudroom and laundry room provide convenience and practicality for everyday living. As you move through the home, natural light pours through large windows, illuminating the meticulous craftsmanship and attention to detail throughout. The expansive living spaces flow effort

Show stopping new construction in the heart of Southampton Village, perfectly positioned just one block from town, offering an effortless blend of luxury, convenience, and lifestyle. Wrapped in a timeless cedar-shingled exterior, this residence seamlessly merges traditional Hamptons architecture with modern, light-filled interiors across 7 bedrooms and 7.5 baths—each thoughtfully designed with radiant heat, including the attached 2-car garage. The home’s open-concept layout is designed for both elevated entertaining and everyday living, with expansive gathering spaces that flow effortlessly from one room to the next. A custom chef’s kitchen with premium appliances and bespoke cabinetry anchors the main level, opening into a sun-drenched great room with fireplace and refined finishes throughout. The formal dining area, complete with a wet bar, connects to a grand paneled foyer and a junior primary suite, while a striking staircase leads to the second level. Upstairs, the primary suite i