luxury houses for rent South Central Connecticut Planning Region, United States

Quiet, wooded living at Quonnipaug Hills in North Guilford, available now. This 2-bedroom, 1.5-bath townhouse rental is set among the trees, with privacy that feels miles away while keeping you in Guilford. The main level has an easy flow: a living room centered on a painted brick fireplace, a dining area with a woven pendant light and sliding doors to a private deck overlooking the woods, and a kitchen with subway tile, stainless appliances, and in-unit laundry just around the corner. A half bath completes the level. Upstairs, both bedrooms have vaulted ceilings. The primary bedroom has a skylight and its own sliding door to a private balcony, and the second bedroom has corner windows looking into the treetops. A full bath serves the floor. A detached one-car garage is included. Step outside to Quonnipaug Lake and the Bluff Head hiking trails, grab coffee and essentials at The Little Store, or stop by Lakeside Feed. Route 77 is a straight shot down to the Guilford town center, the Green, and the shoreline. Heading north, it's an easy commute to Middletown and Hartford. It's located in the Guilford Public Schools district, with all of Guilford's amenities close by. Ready for immediate move-in.

TIMELESS 1910 CHARM MEETS MODERN COMFORT IN DOWNTOWN MADISON! Step into a perfect blend of historic character and contemporary convenience with this beautifully renovated 1910 home in an unbeatable downtown Madison location. From the moment you arrive, the oversized front porch welcomes you to sit back and enjoy the vibrant neighborhood atmosphere. Inside, stunning original hardwood floors and classic vintage features flow throughout a spacious, light-filled floor plan. The expansive living room offers abundant space for gathering, while the updated kitchen provides the modern functionality you need for everyday living and entertaining. Unwind in the cozy sunroom-a serene spot for reading or taking in natural light year-round. Featuring 4 generous bedrooms on the 2nd floor, this home easily adapts to your lifestyle, whether you need dedicated work-from-home spaces or extra guest rooms. Offered partially furnished and situated just moments from local shops, dining, and town amenities, this property delivers the ultimate in-town lifestyle.

Easy ranch living in this corner lot home. Open the the front door and appreciate the living room with vaulted ceiling and open flow to dining room and kitchen. The kitchen features updates appliances and fresh countertops. Access to the deck is through both the kitchen and dining room. A multi-purpose room is set off the dining room and could be ideal for an office or a playroom. Down the hall, you'll find three bedrooms. The primary features hardwood floors and well-appointed full bathroom. There are two additional bedrooms which are served by the stunning hall bath. The laundry is set in the lower level where you'll also access the garage. Outside provides ample yard as well as a spacious deck. This is an outstanding opportunity to live in the recognized Amity School District and also enjoy the ease to shop local stores or access commuter venues. Landlord requires lease/credit check and security deposit. Please provide 24 hours notice for showings. Pets considered on a case by case basis.

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.

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.

Rental Available August 25, 2026- June 15, 2027 An incredible East Rock opportunity. This magnificent 5 BR furnished home is available for academic rent. An elevator takes you to all 3 floors of this amazing home as well as down to the full dry basement perfect for storage. Main floor boasts a Living room, dining room, a huge kitchen that opens to a family room as well as a big deck that leads to a fully fenced in private yard. The second floor has 4 BR's, one with built-ins doubles as a great home office.2 full beautiful new baths. The third floor is fabulous! A private family room, loft, huge bonus room, a bedroom and new beautiful bathroom. Tons of built in bookshelves throughout. Gas heat, central air. Located in the private corner of Everit street across from the park with off street parking. Minutes to Foote school and a short walk to Yale and Downtown New Haven. No smoking. No pets. 700 Minimum credit score. LISTING AGENT MUST BE AT ALL SHOWINGS AND TIMES ARE LIMITED SO PLEASE GIVE PLENTY OF NOTICE Rentspree Application Accepted

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.

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.

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.

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.

SEEKING A 3 BEDROOM FULLY FURNISHED ACADEMIC RENTAL IN A MADISON BEACH COMMUNITY? This lovely home, located in the Neck Road area of Madison, with beach rights, is filled with old world charm but with modern conveniences - large Living Room is the entire front of the home, over looking a screened in porch. There is a dedicated Dining Room, 1st floor Den (office) with pull out couch and access to a renovated full bath and oversized Kitchen. The three bedrooms are on the 2nd floor with a hallway full bath. The neighborhood is one of the most sought after in Madison; Assoc beach is 2 minute walk, surrounding streets provide plenty of walking / running opportunities, neighborhood is quiet and quaint. The home is close to Town, close to I-95 and easily accessible to all other amenities the Town has to offer. House is available from September 15, 2026 to May 15, 2027.

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.

Fabulous academic rental available Sept 8th through May 31st 2026. 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.

Year-round at $7500/mo or Academic at $6500/mo. Discover coveted Madison living on a private beach lane complete with an in-ground pool. Embrace coastal luxury in this stunning 4-bedroom, 5.1-bathroom shoreline retreat. 52 Kelsey Place features a chef-inspired kitchen, central air, 2-car garage, large patio with fire pit and BBQ, inviting fireplace, luxurious steam shower in primary bathroom, outdoor shower, and more. Perfect for entertaining, with room for everyone! Also available for April, May and June at $12,000/mo and or July and August for $20,000.

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

FANTASTIC LOCATION! This 4 bedroom Cape Style home sits on Neptune Ave, just off Liberty Street, with easy access to the private Barberry Farms Assoc Beach and downtown Madison. The first floor hosts a Living Room with fireplace, Dining Room, Den, Sunroom, Primary Bedroom (ensuite) and another bedroom with full bath access. The 2nd floor offers 2 bedrooms, a full bath and oversized Attic / storage room. The home has a two car garage, full unfinished basement, outside bluestone patios, level lot (great privacy in the back) and outdoor shower for post beach afternoons.... The entire interior has been painted and is ready for occupancy. This home is unfurnished and seeking a 6month - 1 year lease. This is a wonderful rental!

4 bedroom Cape with huge fully-fenced back yard. Less than 1/2 mile to middle school, high school, school activities, playing fields and so much more. Enormous great room with tons of natural light and seating options. Close proximity to beaches, town, commuter routes. Available September 1, 2025 or end of August.

Lovely Madison Colonial located on a beautiful cul-de-sac available as of September 16, 2026 for annual, academic or monthly rental. The 1st floor features a pretty kitchen, open family room with fireplace, formal dining room, living room, powder room and bedroom with a full bath. The 2nd floor features a nicely sized primary bedroom with full bath, 2 additional bedrooms and a hallway full bath. The 3rd floor features an additional room that can work as additional guest space or an office. Downstairs you'll find a partially finished area perfect as a playroom or hang out room. Enjoy the change of seasons on the front porch swing or sitting on the private back deck. Take a dip in the above ground pool (open seasonally) or bike around the neighborhood. A terrific house at a terrific price! Tenant pays for ALL utilities. Landlord covers mechanicals, septic and taxes. Excellent credit score required. Non-smoking. No pets.

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 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.

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.

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.

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.