luxury house with pool for rent Cutchogue, United States

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!

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!

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

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!

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

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

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

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: June: $30,000 May: $22,000 Other / Short Term - Year Round: $260,000 August: $70,000 August - Labor Day: $78,000 Memorial Day - Labor Day: $170,000 July - Labor Day: $142,000 July: $70,000

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

This recently renovated and professionally decorated cottage features 3 bedrooms on 0.40+/- acres. The immaculate interior is welcoming and chic, while maintaining the desirable comfort of a beachy summer home. Minutes to both Sag Harbor Village and Southampton, this retreat features new appliances, fresh and stylish furnishings, and interior rooms bathed in natural light. Bar-B-Que on the back deck, swim in the heated pool or in the bay just a short distance away. As part of the Southampton Shores community, the house enjoys access to The Colony Club's private bay beach, pavilion, community tennis and basketball courts. Entertain and enjoy your summer months amidst the private grounds of this attractive Hamptons home. [[Rental Registration # RP260131]] EH RR #: RP260131 Rental Terms: June: $15,000 Two Weeks: $10,500 June/July: $40,000 July: $21,000

Located in a Southampton-North waterfront community, this recently redecorated shingle-style traditional home has been refreshed and decorated with light and bright furnishings, offering comfort and ease in every room. Set on almost a half-acre with in-ground heated pool, the covered front deck opens to an open floor plan starting with the living room with large flat screen TV, and doors out to the large deck. The fully-modern kitchen with stainless steel appliances and stone counters opens to the dining area, and includes a pantry. A separate laundry room, office area, and full bath complete the ground floor. Upstairs, the master bedroom features a flat screen TV, fireplace, and oversized bath. Three more comfortably-appointed bedrooms and full bath finish the second floor. A green yard and attached one-car garage complete the property, and a community gazebo and waterfront area are part of this community. [[Rental Registration # RP261254]] EH RR #: RP261254 Rental Terms: August - Labor Day: $40,000 July - Labor Day: $75,000 July: $35,000

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

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

This modern and chic four bedroom, four bath home has a gourmet kitchen with Miele appliances. The first floor primary suite opens onto the pool terrace. There is also a den on the main floor with ""en suite"" bathroom. Three bedrooms and two baths upstairs. Heated gunite pool surrounded by beautiful manicured gardens. Located by beautiful Conscience Point and bay beaches. All you need for a perfect summer. [[Rental Registration # RP240339]] EH RR #: RP240339 Rental Terms: August - Labor Day: $41,000

Hampton Traditional. Nestled down a private cul-de-sac on 1.2 +/- acres in Southampton North's desirable estate section, Farrel lbuilt home, approximately 6,500 sf, multiple living areas, 5 plus bedrooms, 6.5 marble baths, and a heated Gunite pool. The first floor features a double-height foyer, great room with fireplace and wet bar, living room with fireplace, gourmet kitchen with breakfast area, formal dining room, and a junior primary suite. The second floor offers 5 ensuite bedrooms, including the primary with its own fireplace, laundry, and a bonus room. Additional amenities include coffered ceilings, French doors, top-of-the-line appliances, sound system, 2-bay attached garage, patio, covered porch, over-sized backyard. Beautifully decorated and perfect for summer fun! [[Rental Registration # 230144]] EH RR #: RP250229 Rental Terms: Two Weeks: $60,000 July: $90,000 June: $70,000

New Kitchen Renovation!! Modern waterfront residence with expansive yard and private dock near Long Beach. Enjoy long summer days sailing, kayaking, swimming or swinging in the yard and followed by family bbqs. Great location with proximity to Sag Harbor village restaurants and shops and private outdoor oasis. Revel in spectacular sunset views from the wrap around deck with comfortable seating that is also perfect for outdoor dining and entertaining. Rental Reg. # RP201766 - Reg. Expires 6/07/2023 EH RR #: RP201766 Rental Terms: Other / Short Term - Year Round: $375,000

This gated, 10,000 square foot on 5 park-like acres is the perfect Southampton retreat. The home feels like a true "estate," completely secluded on a private cul-de-sac of high-end homes, well off the main road. The recently refreshed interior is grand, with 5500 square feet of 2-story living space, all on one level, plus an additional 4500 square feet of finished lower level with every amenity. The spacious home offers a 2-story foyer and 2-story living room, with a 20' wall of glass as your first impression. There is plenty of room to spread out. A large eat-in kitchen overlooks the enormous yard. There is dining overlooking the yard, formal dining, and enormous great room with fireplace. A grand primary suite and 3 additional ensuite bedrooms (one can have a queen bed or be a second den with a sofabed) round out the first floor. Given the enormous footprint above, the downstairs affords tremendous living as well. There are two additional guest bedrooms, 2 full baths, theater, game/recreation room and gym area. The gated grounds are simply magnificent--gorgeously manicured, with expansive lawn. The focal point is a 60 x 30 show-stopper pool, surrounded by massive patio and gardens on all sides. An outdoor kitchen with barstools is perfect for entertaining. There is ample outdoor furniture for lounging and dining. The location is convenient, only 1.4 miles to perhaps the Hamptons' prettiest sandy bay beach, Towd Point, 4 miles to Southampton or Water Mill Villages, and 5.5 miles to a dozen ocean beaches. [[Rental Registration # RP250976]] EH RR #: RP250976 Rental Terms: July: $75,000 October: $15,000 February: $15,000 May: $15,000 August - Labor Day: $85,000 Other / Short Term - Year Round: $240,000 April/May: $30,000 April: $15,000 November: $15,000 August: $80,000 January: $15,000 September/October: $35,000 June: $40,000 September: $25,000 March: $15,000 Memorial Day - Labor Day: $185,000

The 5-Acre private estate with sunken Tennis is in a league of its own in Sag Harbor. Be the first to rent this magnificent new build with brand new designer interiors and furniture. Perched on its own hill, this luxurious estate overlooks 278 acres of manicured golf course and reserve on three sides, for privacy and rolling vistas. The expansive backyard is spectacular, with an oversized lawn, landscaping by Marders, and open vistas. It features a resort-like 50' pool with spa, sunbed, waterfall, and firepit. The home spans 3 stories, with 10,500 +/- feet of living space and 7 ensuite bedrooms. High ceilings, 16' sliding glass doors and transom windows contribute a unique sense of light and volume. Other special features include 2 true primary suites (both 1st and 2nd floors), an elevator, custom theater, gym, wine cellar and lower level family room with wetbar (sited off the pool area). The smart home features LED lighting, a 30-speaker sound system, video surveillance and remote-controlled air conditioning and pool. Located in Sag Harbor, the home is minutes to Long Beach and local marinas. It is also equidistant to Southampton, Sag Harbor, Watermill and Bridgehampton. [[Rental Registration # RP241500]] EH RR #: RP241500 Rental Terms: Other / Short Term - Year Round: $800,000 Winter Season: $200,000 Per Month June: $100,000 November: $30,000 March: $30,000 January: $30,000 July - Labor Day: $400,000 February: $30,000 Memorial Day - Labor Day: $475,000 April: $35,000 September: $60,000 July: $190,000 August - Labor Day: $210,000 June/July: $275,000 September/October: $85,000 October: $40,000

This newer construction is a rare find. The inside features high-end, custom furnishings rarely available in a rental at this price. Gorgeous architecture, interior design and mature landscaping will impress. The 7 Bedroom home (all with ensuite baths) spans 5800 feet above ground, plus 2550 feet of finished lower level. The First floor features a dramatic 2-story foyer, 2 spacious living rooms, a chef's kitchen, bar area. There is a Junior Primary, and a mudroom with pool bath. The Second Floor features a Primary suite with terrace, fireplace, and luxurious white marble bath. There are 4 additional ensuite bedrooms and a second laundry. The lower level offers expansive entertainment space, including a theater, living room, and playroom with ping pong. There is a 7th ensuite bedroom with 2 queen beds. Outside, a South-facing large terrace with overlooks a beautifully landscaped, 1-acre property, with farm views. The yard is private and includes a 40' pool, new sunken hot tub and generous patio space for entertaining. The house sits in a very quiet cul de sac of newer homes, 2 miles to Southampton Village, with Southampton beaches just beyond. The property is a short bike ride or walk to the Southampton Rec Center (SYS) which offers a fantastic children's camp, tennis, gym, basketball, track, yoga, and pilates. Its also 1.5 miles to Towd Point Beach, one of the Hamptons prettiest bay beaches. [[Rental Registration # RP230864]] EH RR #: RP230864 Rental Terms: April: $15,000 February: $15,000 Other / Short Term - 1/1/2027 - 4/30/2027: $60,000 November: $25,000 September: $45,000 October: $30,000 January: $15,000 March: $15,000 Winter Season: $90,000 Per Month

Perfectly curated, fully renovated, and designed for effortless summer living, this Hamptons retreat delivers a rare combination of style, comfort, and resort-level amenities. From professionally manicured landscaping to a fully updated, expanded designer interior, the home sets a high standard from the moment you arrive. Inside, an expansive family room anchors the living space with a pool table, fireplace, bar and dedicated TV lounge, flowing seamlessly into another more intimate sitting area with fireplace which leads into the open-concept chef's kitchen featuring high-end appliances, counter seating, and a full dining area-all framed by abundant natural light and views through the oversized picture windows and glass doors. The home offers four en-suite bedrooms. The primary suite is a true retreat, complete with distant water views, a private walk-out balcony, fireplace, and a spa-inspired bath with a generous soaking tub. For added convenience, laundry is located on both the second floor and in the lower level. Outdoors, the property feels like a private resort, featuring a heated saltwater pool, updated decking, and thoughtfully designed dining and lounge areas ideal for entertaining or relaxing in total privacy. A truly special offering designed for elevated Hamptons summer living. [[Rental Registration # RP260341]] EH RR #: RP260341 Rental Terms: Two Weeks: $40,000

This recently renovated and impeccably maintained Water Mill residence with five bedrooms and four-and-a-half baths, located on a quiet cul-de-sac, offers the ideal setting for entertaining and relaxing. Sited on over an acre, the property features a beautifully landscaped, private rear yard with a heated, lighted 20' x 40' Gunite pool surrounded by a heat-resistant patio, with an outdoor kitchen featuring fridges, Lynx Infrared searing barbeque for summer grilling, expansive rolling lawn, and two firepits perfect for star-filled evenings with a Sonos sound system inside and outside. The main level includes a welcoming den with a gas fireplace, a comfortable living room, a gourmet kitchen outfitted with Viking professional appliances, dual dishwashers, wine fridge, ice maker, water cooler, and a generous center island, along with a spacious dining area for hosting family and friends. Upstairs, the serene primary suite offers a king-sized bed, Peloton, and a luxurious bath complete with a soaking tub, Toto Washlet, and double vanities. The second floor also includes an ensuite guest room, two additional bedrooms sharing a hall bath, and a convenient laundry room. The finished lower level with 10-foot ceilings includes a second laundry area, fridge, microwave and sink. It also provides a fifth bedroom, full bathroom, recreation room with pool table, ping pong, and an extensive game system, as well as a gym with a treadmill, free weights, incumbent bike and TV. Located moments from farm stands, world-class ocean beaches, transportation, and the vibrant communities of Southampton Village, Bridgehampton, and Sag Harbor - known for their marinas, dining, cultural venues and shopping - this Water Mill retreat delivers the very best of Hamptons vacation living. Rental Terms: Two Weeks: $25,000 Other / Short Term - 5/22/2026 - 6/26/2026: $50,000

Minutes to ocean and bay beaches, farmstands, and the best that Water Mill and Bridgehampton have to offer, this one-of-a-kind gated estate delivers an unparalleled blend of Hamptons luxury and Western character. Surrounded by 50+/- acres of reserve, the 18-acre property offers total privacy with equestrian amenities, including paddocks, two stalls, and a professional Grand Prix riding arena. Featured on the cover of Architectural Digest's "Country" issue, this is a stay you won't find elsewhere. The custom Montana-built log home boasts four bedrooms, five full and two half bathrooms, designer furnishings across two levels, four fireplaces, a full movie theater, and a dedicated gym. Outdoors, enjoy a heated pool; outdoor dining, bar, and grilling areas; expansive grounds; and direct access to nature. Full-time groundskeeper/barn manager on-site. [[Rental Registration # RP251906]] EH RR #: RP251906 Rental Terms: Other / Short Term - Dec: $40,000 November: $40,000 Memorial Day - Labor Day: $295,000

Brand new furnishings await the discerning tenant at 18 Spring Pond located in a quiet, private community. The 2 story home offers a heated, gunite swimming pool and community tennis court. The house is freshly painted, updated and boasts brand new furnishings including pool lounges. Great open floor plan from the kitchen to indoor and outdoor entertaining spaces. There is a junior en-suite bedroom on the first floor in addition to a powder room. The second floor holds the private primate suite with floor to ceiling windows overlooking the private property. There is a private balcony, shower bath, walk in closet and an adjacent den that can serve for relaxation, working. There is a third en-suite guest room with two twin beds and the laundry room on the second floor. [[Rental Registration # RP260246]] EH RR #: RP260246 Rental Terms: Other / Short Term - Dec: $15,000 April: $15,000 July: $40,000 September: $18,000 March: $10,000 November: $10,000 June/July: $60,000 May: $15,000 January: $10,000 October: $10,000 February: $10,000 Winter Season: $60,000 Per Month

A Refined Hamptons Retreat - Available for the U.S. Open in June** Discreetly positioned amid rolling farm fields, this sophisticated Water Mill residence offers an exceptional blend of elegance, comfort, and timeless summer living. Thoughtfully designed and furnished, the six-bedroom, six-bath home with one powder room welcomes with sun-drenched interiors, gracious proportions, and beautifully curated finishes throughout. The main living spaces flow effortlessly to a covered porch overlooking the impeccably maintained grounds, where an in-ground, heated gunite pool and spa create a serene outdoor sanctuary ideal for both intimate relaxation and refined entertaining. A fully finished lower level adds an additional layer of leisure and versatility, enhancing the home's sense of ease and livability. Perfectly situated between pristine ocean beaches, distinguished Hamptons villages, renowned dining, and coveted local amenities, this residence provides the convenience of proximity while preserving the tranquility of a private country setting. An immaculate offering for discerning summer guests - and a premier opportunity for those seeking a luxurious stay during the U.S. Open this June.** Rental Terms: August - Labor Day: $110,000 July: $100,000 July - Labor Day: $210,000 August: $100,000