luxury houses for rent Madison, United States

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.

Relocating to the area? House hunting and yet to find the perfect home? Perhaps looking to spend the academic year along the gorgeous CT shoreline? Look no further as you've found the perfect spot to hang your hat for the academic year here at 32 Tuxis Road. This home is a beautifully restored, quintessential Madison beach house available for rent from September 8, 2026 - June 30, 2027. Originally built in 1915, and maintaining much of the original architecture, this renovated home offers a blend of old world charm and modern luxuries. Desirable open floor plan, chef's kitchen, 5 well sized bedrooms, 4.5 bathrooms and walkable to 3 beaches this house offers all you could desire from a rental. Immaculate condition and desirable location! Dogs considered. Landlord to cover cable, wifi, landscaping, snow plowing and trash removal. Tenant to cover electricity, water, propane and all other utilities. No garage bays and large primary walk-in closet available. Two month's security required.

Coastal Meets Retro in this adorable Cottage Style Home Near East Wharf Beach in Madison, CT !! Furnished 2 bedroom, 1.5-bathroom cottage rental in Madison, Connecticut - an academic-year lease a short distance from East Wharf Beach on the Connecticut Shoreline. This fully furnished Madison cottage blends a relaxed beach-house feel with mid-century character, including a vintage-style blue refrigerator in the kitchen. The layout offers two bedrooms, one and a half bathrooms, and a dedicated smaller room ideal for a home office or study. Recent updates include new windows (2026)- on order and will be installed in August, updated flooring throughout, making this a turnkey, move-in ready rental. Available fully furnished for the academic year, [September] through [May]. Minutes to East Wharf Beach, Madison town center, Boston Post Road shopping and dining, and Long Island Sound. One dog or small pet considered; no cats. . A rare furnished seasonal rental on the Connecticut Shoreline in Madison, CT 06443.

Daydreaming about waking up to the sounds of waves and walking to your very own private beach? Make your dreams come true at 118 Middle Beach Road! With 7 bedrooms, 5 full baths, and 2 half baths, this iconic property comfortably accommodates up to 14 guests. The main level is an entertainer's paradise featuring an oversized kitchen, formal dining area, living room with views from every angle, and generously-sized screened-in porch! In addition to six of the seven bedrooms, the second floor features a family room perfect for kicking back and soaking in the expansive views! The third floor is a private retreat with the seventh bedroom and enormous recreation room. Let's also remember the large, water-facing screened-in porch perfect for soaking in the sunrise and sunset each day. Just outside, sun, sand, and saltwater air await you! This is the perfect place to be this summer - schedule your private viewing today and enjoy your own private beach in a few short months! One month for $45,000, two weeks for $22,500 or one week for $12,500. Please reach out to listing agent for most up-to-date availability.

ACADEMIC RENTAL! The iconic, water-front 118 Middle Beach Road is available for rent for the academic year beginning October 1, 2026. This sensational property offers comfortable occupancy for up to fourteen people with 7 bedrooms, 5 full baths, and 2 half baths. The main level is an entertainer's dream featuring an oversized, eat-in kitchen, formal dining area, living room with water views from every angle, and generously-sized screened-in porch! In addition to six of the seven bedrooms, the second floor features a family room perfect for cozy afternoons soaking in the expansive views and stunning sunsets! The third floor is a private retreat with the seventh bedroom and spectacular recreation space. Outside, your very own, private beach awaits you! Schedule your viewing today and make "Red Top" your home for the academic year! Short-term rental also available; please inquire.

Academic rental available Sept through June! Stunning,spacious 4BR, 3BA Colonial perfectly situated close to town, schools,vibrant shopping,and local beaches. This inviting home features a light-filled living room with fireplace, formal ding room, functional eat in kitchen, separate family room, a private main level office, and a charming porch. Enjoy comfort, premium convenience, and a prime coastal-town lifestyle for the academic term.

This meticulously cared for ranch offers the ideal blend of comfort, style, and convenience-all just moments from town. Set on a stunning private property, the home's setting, condition, and location make it a rare rental opportunity. Step inside to a one level layout filled with charm and thoughtful updates. The newly refreshed kitchen features brand-new appliances, updated countertops and backsplash, and gleaming hardwood floors. A dedicated laundry room adds everyday convenience. The sunroom, equipped with a new ductless split system, opens to a wraparound deck where you can relax and take in the peaceful surroundings. The family room is warm and inviting with its fireplace, while the dining room flows seamlessly into a bright, natural light filled living room-also with a fireplace. The bedroom wing includes a spacious primary suite with a newly renovated bath and walk in closet. Three additional bedrooms and a gorgeous brand-new full bath complete this private area. The large basement provides partial storage space, and the attached two car garage adds even more practicality. One of the best features of this property is its unbeatable location-just a short walk, bike ride, or drive to downtown Madison, East Wharf Beach, the train station, and I95. A rare chance to enjoy privacy, convenience, and quality living in one exceptional home.

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.

ANNUAL UNFURNISHED RENTAL, AVAILABLE IMMEDIATELY. Located between downtown Madison and the Hammonasset State Park Beach, this 3 bedroom renovated ranch offers a comfortable life style. The house offers a deck to enjoy the outdoors, large yard, easy access to the Shoreline Greenway Trail and beach access at the end of Webster Point Road. The primary bedroom has a full bath, the other two bedrooms share a full bath. AC is via window units and heat is electric. This house is cute and comfortable. Some pets considered.

FURNISHED RENTAL AVAILABLE - September 1, 2026 to May 31, 2027. Comfortable and nicely decorated, this home has 2 bedrooms upstairs that share a newer renovated full bath. This home is located in a private association with access to the Overshores Beach, one of the nicest association beaches on Neck Road. Recently renovated kitchen, newer mud room, newer first floor full bath, laundry room on 1st floor, sunny year round office on the south side of the home, and outdoor shower. Walk / bike to downtown Madison. No smoking permitted. NO PETS. Credit check and security deposit required.

Available from September 15, 2026, through May 15, 2027, this stunning direct-waterfront academic rental offers an unparalleled coastal lifestyle with breathtaking, panoramic views from almost every room. The bright, sunny interior features an open-concept main level, highlighting a gourmet kitchen with quartz countertops and stainless steel appliances, alongside a generous living and dining area complete with a gas fireplace and walls of glass that frame the ever-changing coastal vistas. Sliders open to an expansive wrap-around deck perfect for relaxing, while the direct-access beach with its natural tidal pools awaits just steps away. The home's flexible layout includes a convenient main-floor bedroom with a full bath and laundry, while the upper level boasts a second bedroom, a full bath, and a one-of-a-kind primary suite featuring soaring ceilings, dramatic walls of glass, and a private balcony for your morning coffee. Please note that this is a strict no pets, no exceptions property.

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.

37 Beach Avenue is ready to welcome its next resident! Simply cute as a button, perfectly positioned off Neck Road and just a short stroll to the shore - complete with beach rights - this is the coastal retreat you've been waiting for! One look and you'll surely feel right at home. Featuring two bedrooms, one full bathroom, on-site, main-level laundry, and a wonderfully sized yard, this adorable abode has all the makings of an ideal, long-term rental. Let's also remember the recent upgrades including a new range and range hood, upgraded electrical, new exterior door, freshly painted interior, and professionally cleaned carpet! All that is left to do here is move in and enjoy the beach and salt-water air! This gem will be scooped up quickly - schedule your private tour today and move in before summer's end!

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.

AVAILABLE FOR MONTH OF JUNE 2026. 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 a 1 month rental, this home offers a lifestyle of comfort and relaxation. NO PETS.

4 Bedroom Renovated House across from Private Beach in Bucolic Madison, Connecticut Available Oct 1- May 15 but flex term. This sunny 4 bedroom/3 bath house with home office and water views is located at the end of a quiet road across from coveted Hartford Avenue beach. The main floor has a large, renovated eat-in-kitchen, spacious living room with gas fireplace, substantial dining area, reading nook, screened porch with dining and seating area, bedroom and full bath. The 3rd floor consists of the large principal suite with separate sitting area, deck with water views, and renovated en-suite bath with double sinks, separate tub and glass walk-in shower. The 2nd floor has 2 additional bedrooms, hall bath, windowed office, sitting area and laundry. A lovely front yard, water views, and beach access across the street complete the picture. $4600 per month. The house is 10 minutes from the historic and charming towns of Madison and Guilford, Ct and conveniently located midway between NYC (just under 2 hours) and Boston. Nearby is a cinema, nationally acclaimed bookstore, gym, pilates, library, tennis and wonderful shops. One dog on a case by case basis, sorry no cats. Renters responsible for cleaning $170(per visit), utilities, garbage pick-up, snow removal

Fabulous academic rental available Sept 1st through May 31st 2027. This direct waterfront four bedroom home set on a one of kind property with access to a private beach. Enjoy fabulous views from your deck, large yard and tidal pool. Plenty of space for everyone with a bedroom with full bath on the main level, Primary en suite on the second floor with private balcony and two additional bedrooms with full bath; this home will sleep 8/9 guests comfortably. Central Air in the main house and every convenience you could possibly want.

Available for the Sept 10th 2026 through June 10th 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. Some Pets considered.

Historic Charm Meets Modern Luxury: Carriage House Living in Downtown Guilford Experience the quintessential Shoreline lifestyle in this stunning, light-filled carriage house at 200 Whitfield Street. Tucked privately away in heart of downtown Guilford, this unique residence seamlessly blends historic architectural character with high-end, contemporary updates. Step inside to breathtaking open-concept living defined by soaring post-and-beam vaulted ceilings, exposed timber trusses, and rich wide-plank hardwood floors. The sun-drenched main space features skylights, expansive windows, and a chef's kitchen complete with white shaker cabinetry, sleek dark countertops, a gas cooktop island with breakfast bar, and stainless steel appliances. The living space flows effortlessly to a pristine, updated full bath featuring a custom tile and glass walk-in shower, alongside a convenient dedicated laundry and storage room. Every corner of this property radiates historic warmth, style, and total comfort. Best of all, your location is unmatched. Leave your car behind and take a short stroll to the historic Guilford Green, boutique shopping, local cafes, fine dining, the Guilford Free Library, and the shoreline train station. Jacobs Beach and Guilford Harbor/Marina are just down the road. An extraordinary rental opportunity in an unbeatable downtown location.

Renovated 2-bedroom, 2-bathroom cottage for rent at 98 Union Street in Guilford, Connecticut - walking distance to Guilford Green, the town center, restaurants, and shops. This shingle-style home, named Seascent, pairs a classic Shoreline exterior - white siding, picket fence, and blue front door - with a fully updated interior. The open-concept main level features vaulted ceilings, hardwood floors, and a chef's kitchen with a navy blue island, quartz countertops, stainless steel French-door refrigerator, gas range, and stainless range hood. Globe pendant lighting hangs above the island, and a built-in banquette dining nook and living area with sectional seating complete the main floor. A built-in ladder leads to a loft space, adding flexible square footage above the living room. The primary bedroom offers a vaulted ceiling, shiplap accent walls, and a walk-in closet-ready dresser wall. A second bedroom provides comfortable guest or home-office space. Both full bathrooms have been updated, including a double-vanity bath with stone countertops, black matte fixtures, and tree-print wallpaper. Outside, a private paver patio in the fenced backyard offers space for outdoor seating and entertaining, and a personal driveway provides off-street parking - a rare find this close to downtown Guilford. Available August 15 on a 12-month lease. Tenant responsible for all utilities. No pets. Located within walking distance of Guilford Green.

Academic Rental Late September -May 31, 2027. Charming 3-bedroom, ranch-style home in the Harbor View Beach Association. Large living room, 3 generous bedrooms, updated kitchen and bath just steps to the association beach.