luxury houses for rent New Haven County, United States

A TRUE MADISON WATERFRONT (No street or HOA in front) FOR JUNE 20th - JULY 7th. 17 Days including the JULY 4th WEEK to enjoy America's 250th Birthday & Madison's big celebrations; Concert on the Green, Parade, Fireworks & more! With incredible views out over Long Island Sound & beyond this light & bright Beach Colonial was newly built in 2006 plus has a recent 3 BR room addition & renovated Baths! Featuring an open floor plan, all in excellent condition with lots of glass & a wrap around deck to take full advantage of it's setting. Located at the very end of a private street this special home is in a nice quiet setting. Hardwood floors both up & down, central vac, a first floor den with sleeper couch that is perfect for those unexpected guests with a full bath right around the corner, newer propane heat and fully air conditioned. Set up high on piers, you'll feel like you are on a boat! Enjoy awesome sunrises AND sunsets from a single location! Unique opportunity. A shorter stay for the July 4th week only will be at a premium.

SEPT '26 - MAY '27 ACADEMIC WATERFRONT RENT Plan ahead. With amazing views out over Long Island Sound & beyond this light & bright Beach Colonial was built in 2006 plus has a recent 3 BR addition! Featuring an open floor plan, all in excellent condition with lots of glass & a wrap around deck to take full advantage of it's setting. Located at the very end of a private street this special home is in a nice quiet setting especially in the off season. Hardwood floors both up & down, central vac, a first floor den with sleeper couch that is perfect for that unexpected guests with a full bath right around the corner, newer propane heat and fully air conditioned. Set up high on piers, you'll feel like you are on a boat! Enjoy awesome sunrises AND sunsets from a single location! August might be available too. Exact dates to be determined. Unique opportunity.

Experience New York-style sophistication in this stunning townhouse apartment located in the vibrant center of downtown Milford. This residence masterfully blends modern urban aesthetics with coastal charm, offering a refined and peaceful living environment just steps from the energetic Milford Green. Spacious open-concept layouts with high-end finishes that evoke a true Manhattan loft feel, perfect for both daily living and effortless entertaining. Retreat to your own outdoor sanctuary, ideal for morning coffee or evening relaxation under the stars. Benefit from easy access to the train station, I-95, and the Merritt Parkway for a seamless regional commute. Easy access to top-tier restaurants, cozy coffee shops, tennis courts, and local parks. Enjoy immediate proximity to seasonal events, boutiques, and the vibrant culture of the Milford Green. No Smoking

Welcome to 14 Island View Ave-a masterfully redesigned coastal retreat nestled in the heart of highly desirable Pine Orchard. Spanning 2,100 square feet, this thoughtfully renovated home seamlessly blends modern luxury with relaxed shoreline living. Boasting 5 spacious bedrooms and 2.5 beautifully appointed baths, the residence features a bright, open floor plan optimized to capture gorgeous, unobstructed water views. Every detail has been meticulously curated during its full remodel, offering an unparalleled turn-key experience in one of the area's most coveted neighborhoods.

DIRECT WATERFRONT with unobstructed views of Long Island Sound. LIFE IS BETTER AT THE BEACH. Available for the month of June. Amazing home to gather with friends and family offering large open floor plan, 5 bedrooms, large 3rd floor rec room, porch for al fresco dining...Don't feel like cooking? Head over to the Madison Beach Hotel & treat yourself to cocktails, lunch, dinner with amazing views. Life is Short...Enjoy Madison at its finest.

Enjoy direct waterfront living in desirable Stony Creek with sweeping views of the Thimble Islands and Long Island Sound. This fully furnished, renovated home features an open floor plan with a spacious kitchen, dining area, and great room, all designed to capture the water views. The main level includes a sitting room and half bath. The second floor offers a primary suite with full bath and water views, a guest bedroom with en-suite bath, two additional bedrooms, and a third full bath. Hardwood and tile flooring throughout. Outdoor features include a front porch and patio overlooking the water. A gently rolling lawn transitions to a natural stone shoreline, complete with a private dock ideal for small watercraft. Located in Stony Creek Village near shops, restaurants, hiking trails, and the Legacy Theatre. Just minutes to downtown Branford, 10 minutes to New Haven, and approximately 75 miles to NYC. Spend the month of August in this beautifully appointed home, ideally located to enjoy all that the shoreline has to offer. Available for August rental at $20,000. Also available for academic rental.

Direct Waterfront Academic Rental in Stony Creek Available 9/1/26 - 5/31/27 Enjoy direct waterfront living in desirable Stony Creek with sweeping views of the Thimble Islands and Long Island Sound. This fully furnished, renovated home features an open floor plan with a spacious kitchen, dining area, and great room, all designed to capture the water views. The main level includes a sitting room and half bath. The second floor offers a primary suite with full bath and water views, a guest bedroom with en-suite bath, two additional bedrooms, and a third full bath. Hardwood and tile flooring throughout. Outdoor features include a front porch and patio overlooking the water. A gently rolling lawn transitions to a natural stone shoreline, complete with a private dock ideal for small watercraft. Located in Stony Creek Village near shops, restaurants, hiking trails, and the Legacy Theatre. Just minutes to downtown Branford, 10 minutes to New Haven, and approximately 75 miles to NYC. Utilities not included.

WATERVIEW SUMMER RENTAL AVAILABLE FOR JULY ONLY as August is now rented. This quintessential Seasonal Beach Cottage with WATER VIEWS is special The views out over Long Island Sound AND a wonderful wraparound South facing Open Porch to catch the summer breezes are both part of this charming Cottage, located directly across from the very desirable private Overshore (SANDY) Beach Association with it's large grass play area, boardwalk, gazebo & even a raft!, Besides the water views from every room, a light & bright open floor plan, high ceilings, a small but cool sleeping porch/room, new ceiling fans, updated Bathrooms, full size washer & dryer and an outside hot/cold shower, the Kitchen has granite counters, stainless appliances including a dishwasher & a butler's pantry. Also OFF SEASON in May & June or September & October possible too at a lesser rate. One time $350 cleaning fee. Sleeps 9.

Embrace the serene beauty of Middle Beach with this exquisite academic rental, available from September 15th through May 15th, 2027. This direct waterfront property offers a tranquil retreat with open-concept living and breathtaking views of the water. The main level is designed for comfort and elegance, featuring a cozy gas fireplace, an updated kitchen with modern amenities, a convenient dry bar, and the first of three full bathrooms. As you ascend to the second level, you'll find four well-appointed bedrooms and two additional full baths, ensuring ample space to comfortably accommodate six guests. Wake up to the soothing sights of the shoreline in the primary bedroom, which boasts panoramic water views, a spacious walk-in closet, and an en-suite bathroom equipped with a stall shower and double sinks. The third floor unveils a hidden gem: a deck and office nook that present the ideal vantage point for witnessing the captivating sunsets that Middle Beach is known for. This space provides a peaceful haven for work or relaxation, enveloped by the natural splendor of the coast. While some pets may be considered, please note that cats are not permitted. This property is a rare opportunity to experience coastal living at its finest during the fall, winter, and spring months. Don't miss the chance to call this waterfront haven your temporary home.

Enjoy the beach this summer! A rare year-round rental in the coveted Hartford Avenue beach community. This charming home offers a first-floor primary bedroom and a brand-new main-level full bath. Also found on the first level are a kitchen, dining room, living room, family room, 2 fireplaces, a washer and dryer, and an additional brand-new half-bath. Two bedrooms and a brand new full bath are found on the second floor. Enjoy a wonderful enclosed porch, an outside patio, and a large level yard. A private sandy beach is just a short stroll away. Whether it's the energy of the summer or the peaceful solitude of winter, this location is ideal for enjoyment throughout all four seasons. Convenient to town, restaurants, shopping, the town green, and schools. Don't miss your chance to secure a year-round piece of paradise on the CT shoreline.

Enjoy the best weeks of summer in Madison in this exceptional, academic rental! Available August 10th, this beautifully-crafted residence offers the ideal blend of comfort and tranquility, just minutes from the shoreline and town center. The thoughtfully designed interior features a welcoming living room with gas fireplace, creating an inviting atmosphere for evening reading or entertaining family and friends. The well-appointed kitchen with custom cabinetry and granite countertops flows seamlessly into a charming dining area -perfect for hosting gatherings or quiet meals.The dedicated den/office provides an ideal space for working from home. A convenient half bath with laundry room completes the main level. Upstairs, the primary suite is a peaceful retreat with a full bath, complemented by two additional bedrooms and another full bath. The basement is partially finished providing the possibility for an in-home gym, recreation room, secluded office, additional storage space or all of the above! The private, fully-fenced backyard sanctuary features a stunning bluestone patio and custom wood-burning fireplace, offering a serene environment for outdoor relaxation, and the two-car, detached garage adds practical convenience. This property is the perfect setting for professional pursuits while maintaining access to coastal amenities and a plethora of commuting options. With so much to offer, make sure to view 41 Liberty Street today!

Welcome to your own private sanctuary at 236 Clintonville Road in North Haven. This meticulously maintained single-story ranch offers approximately 1,300 square feet of sophisticated living space, perfectly designed for those who appreciate quality over quantity. The heart of the home is a stunning, high-end kitchen that flows seamlessly into an open-concept layout, all anchored by gleaming hardwood floors that run throughout. Large windows invite an abundance of natural light to fill every corner, creating an airy and vibrant atmosphere that makes the home feel incredibly spacious. Beyond the interior, the property transforms into a personal retreat. The bedroom and bathroom are thoughtfully proportioned for comfort, complemented by a dedicated laundry room that adds a layer of modern convenience. Step outside to find the home's crowning jewel: a beautiful, custom pergola that serves as the centerpiece of the backyard. Whether you're hosting an intimate dinner or enjoying a quiet morning coffee, this outdoor space feels like a secluded getaway far removed from the hustle and bustle. This 1-bedroom gem is a rare find, combining upscale finishes with a tranquil, low-maintenance lifestyle.

Available for the Sept 2026 through June 2027. This sun- filled colonial has been lovingly restored for easy comfortable living. Open views of the Long Island Sound throughout this home offers room for all. Screened in wrap around porch to enjoy the warm days and nights. Updated kitchen with stainless appliances and large dining nook, mud room, office and dedicated laundry room and half bath all found on the main level. Four levels of living make this the perfect home for multi generations: with a main level bedroom with Queen bed, Primary Suite on the second level with en-suite bath and office nook with a private balcony, second bedroom with bunks -on the third level is the fourth bedroom with twin beds, shared full bath on the second level. Lower level has a rec/play room. Access to the Soundview Association beach.

AVAILABLE FOR THE MONTH OF JULY. Classic Madison charm meets modern family living in this inviting 4 bedroom Colonial on Wildcat Road. Step through the front door to discover hardwood floors that flow throughout, two fireplaces that add warmth and character, and an extra-large (front to back) Living Room perfect for gatherings large and small. Gardeners will love the Greenhouse, right off the Dining Room! Just off the Living Room leads to a delightful screened porch-ideal for morning coffee or summer dinners-and a spacious patio for outdoor entertaining. The walk-out lower level is completely finished and currently serves as a generous family room, offering a wood burning stove, spacious laundry area, flexible space for play, relaxation, or entertaining. Located close to Madison's charming town center and the Town Campus, this home delivers both convenience and community. As a special bonus, enjoy access to the inground pool next door-a rare perk that makes summer living effortless. Whether you're hosting friends, enjoying quiet evenings by the fire, or exploring all that Madison has to offer, this home provides the perfect backdrop for everyday life and lasting memories.

AVAILABLE FOR THE MONTH OF JUNE. Classic Madison charm meets modern family living in this inviting 4 bedroom Colonial on Wildcat Road. Step through the front door to discover hardwood floors that flow throughout, two fireplaces that add warmth and character, and an extra-large (front to back) Living Room perfect for gatherings large and small. Gardeners will love the Greenhouse, right off the Dining Room! Just off the Living Room leads to a delightful screened porch-ideal for morning coffee or summer dinners-and a spacious patio for outdoor entertaining. The walk-out lower level is completely finished and currently serves as a generous family room, offering a wood burning stove, spacious laundry area, flexible space for play, relaxation, or entertaining. Located close to Madison's charming town center and the Town Campus, this home delivers both convenience and community. As a special bonus, enjoy access to the inground pool next door-a rare perk that makes summer living effortless. Whether you're hosting friends, enjoying quiet evenings by the fire, or exploring all that Madison has to offer, this home provides the perfect backdrop for everyday life and lasting memories.

AVAILABLE FOR THE MONTH OF AUGUST. Classic Madison charm meets modern family living in this inviting 4 bedroom Colonial on Wildcat Road. Step through the front door to discover hardwood floors that flow throughout, two fireplaces that add warmth and character, and an extra-large (front to back) Living Room perfect for gatherings large and small. Gardeners will love the Greenhouse, right off the Dining Room! Just off the Living Room leads to a delightful screened porch-ideal for morning coffee or summer dinners-and a spacious patio for outdoor entertaining. The walk-out lower level is completely finished and currently serves as a generous family room, offering a wood burning stove, spacious laundry area, flexible space for play, relaxation, or entertaining. Located close to Madison's charming town center and the Town Campus, this home delivers both convenience and community. As a special bonus, enjoy access to the inground pool next door-a rare perk that makes summer living effortless. Whether you're hosting friends, enjoying quiet evenings by the fire, or exploring all that Madison has to offer, this home provides the perfect backdrop for everyday life and lasting memories.

6 WEEKS OF BLISS!! THINKING OF RENTING A CHARMING HOUSE IN MADISON FOR THE SUMMER? Available from July 19, 2026 to August 30, 2026. The Landlords are seeking a renter to take the entire term (no weekly or 2 week rentals available). Called The Wendell Farm, this 3 bedroom home has a chef's kitchen, hardwood floors, open floor plan, and newly added Master Suite in 2008. Spectacular Madison Beaches are a 5 minute drive away. Downtown Madison is 3 minutes away. The public middle school across the street, Polson Middle School, has tennis courts and playing fields. The property is complete with the quintessential red barn. Come experience the easy summer lifestyle in Madison. Landlords and house are pet friendly. Tenant pays for electricity.

Sneak away from the hustle and bustle and spend the month of August at Captain Eber Judd House (circa 1740). This historical gem, reminiscent of Nantucket and Essex Whaling Captain's homes, oozes charm with its stunning wide plank floors, beams, and original fireplaces. Located in the heart of downtown Madison, it's just steps from the gorgeous beach, the quintessential downtown, and the Friday Farmer's Market. This home shines with historical moments, yet it is appointed with modern amenities, making time spent here a delight. Enjoy coffee in the morning in the three season sunroom, a glass of wine and views of the Long Island Sound by the firepit (s'mores anyone?), afternoon snoozes on the back terrace or cozy up with a book in the library or family room. The 1st floor features the cook's kitchen, elegant dining room, family room, library, sunroom, study, laundry room, and a full bath. You'll find 3 bedrooms and 2 full baths on the second floor. Tucked away, yet close to everything, this home is a wonderful place to hang your hat for the month of August. Truly one of a kind! Simply drop your bags and exhale. No pets or smoking, excellent credit is required.

Experience the ultimate coastal lifestyle in this sun-drenched, TOP FLOOR condo at 185 Melba Street, Unit #305 located in the sought-after Breaker Beach community of Milford. This 823-square-foot home perfectly balances modern interior updates with the serene atmosphere of waterfront living. The Updated Kitchen features sleek granite countertops, custom cabinetry, and updated appliances. Your own private screened-in Balcony is located off the living area, for year-round enjoyment, offering peaceful water views and refreshing sea breezes. Enjoy the peace and quiet of a top-floor unit with no neighbors living above you! Living at Breaker Beach feels like a permanent vacation with direct access to Long Island Sound. Step out of the building and onto the private association beach which offers a dedicated barbecue and picnic area overlook the water, and the calm local waters - perfect for kayaking, swimming, or paddleboarding. Convenience features include secure building with elevator access, a laundry room and dedicated storage space in the basement and plenty of parking for residents and guests. Located in the charming Point Beach/Woodmont area, you are just a short drive from Milford Town Center, known for its historic green, boutique shopping, and vibrant dining scene. Convenient access to the Milford Train Station and major highways, blending a tranquil beach retreat with easy accessibility.

AVAILABLE EARLY SEPTEMBER TO THE END OF MAY, 2027. Classic Madison charm meets modern family living in this inviting 4 bedroom Colonial on Wildcat Road. Step through the front door to discover hardwood floors that flow throughout, two fireplaces that add warmth and character, and an extra-large (front to back) Living Room perfect for gatherings large and small. Gardeners will love the Greenhouse, right off the Dining Room! Just off the Living Room leads to a delightful screened porch-ideal for morning coffee or summer dinners-and a spacious patio for outdoor entertaining. The walk-out lower level is completely finished and currently serves as a generous family room, offering a wood burning stove, spacious laundry area, flexible space for play, relaxation, or entertaining. Located close to Madison's charming town center and the Town Campus, this home delivers both convenience and community. As a special bonus, enjoy access to the inground pool next door-a rare perk that makes summer living effortless. Whether you're hosting friends, enjoying quiet evenings by the fire, or exploring all that Madison has to offer, this home provides the perfect backdrop for everyday life and lasting memories.

Beautifully renovated half duplex, townhouse style unit located in Morris Cove, just steps from the Pardee Seawall Park! Newer vinyl laminate flooring throughout the main floor, upper level, and finished third floor. Updated kitchen with quartz counter tops, stainless steel appliances, and cabinets. Both bathrooms with quartz top vanities, and a full wall of a marble backsplash in the upper level full bathroom. Finished third floor flex space with skylights, and a basement with laundry and plenty of room for storage. Enclosed three season porch and a fenced in back yard. Close to Fort Hale Park, Lighthouse Point Beach, major highways, Yale, downtown, and so much more!

AVAILABLE FROM EARLY SEPTEMBER 2026 TO END OF MAY 2027! Welcome to this enchanting 4 bedroom, 2 full bath home, where the beach is just a half-block stroll away! Located off Neck Road, 1 mile from the heart of Madison, CT, this residence offers the perfect blend of coastal charm and convenience. As you enter, the first floor greets you with a Family Room, through to a Kitchen, then onto the Living Room. The sunroom is a tranquil space to unwind, offering views of the outdoors and filling the home with warmth year-round. The 1st is rounded out with 2 well appointed bedrooms. The second floor is a private retreat featuring the oversized Primary Bedroom and an additional bedroom, each designed to provide a peaceful escape with ample space and comfort. Step outside to the expansive outdoor deck, where you can soak up the sun or entertain guests in the sea breeze. The fenced yard ensures privacy, while the patio with an awning offers a shaded sanctuary for those long summer days.This home's prime location near the beach allows for endless days of sand and surf, while the close proximity to downtown Madison ensures all the conveniences of town living are just moments away. If you are seeking an academic rental, this home offers a lifestyle of comfort and relaxation. NO PETS.

Furnished Studio Apartment- Available May 15th- Sept 15th. The studio is graced with stunning views of Fence Creek, providing a picturesque backdrop to your daily living. Just steps away from the sandy shores of East Wharf Beach and the vibrant Madison town center, you'll have the best of coastal living right at your fingertips. Designed with efficiency in mind, the space features a queen bed that effortlessly converts into a couch, allowing you to maximize the living area during the day. The apartment is equipped with a modern split system to ensure your comfort in all temperatures, and the convenience of an in-unit washer and dryer adds to the ease of your stay. Whether you're seeking a tranquil spot to unwind or a base to explore the local attractions, this studio apartment is the ideal choice for a memorable summer getaway. Embrace the laid-back lifestyle of Madison and let the gentle sea breeze and calming creek views soothe your soul.

JULY &/OR AUGUST ~ Enjoy One or Two Months in Madison for 2026 at a Price you can't beat !! Summers in Madison are what they're cracked up to be !! Spend your Days one of 3 Local Manicured Sandy Beaches (East Wharf, West Wharf or the Surf Club) all located Directly on Long Island Sound. When the day is done, head Back Home for the Tranquility of this Country Cape on a Private and Secluded Hillside ~ Chill & Grill on the Outside Patio as the Sunsets over the Rear of the House. Take advantage of Sundays Free Concerts on the Green, Thursdays music events at Madison Beach Hotels The Grassy Strip and don't forget to pick up something Fresh on Fridays from The Farmers Market on the Green.