luxury seaside house for rent Old Saybrook, United States

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.

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.

To MAY '27 ACADEMIC WATERFRONT RENT 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! Exact dates to be determined. Unique opportunity.

WONDERFUL 4 BEDROOM VINTAGE SUMMER HOME, AVAILABLE FOR THE MONTH OF AUGUST 2025. Renovated but with old world charm - plenty of gathering areas for family and friends in Living Room, Dining Room, Sun Room and outdoor patio. Kitchen was renovated, along with 1st floor bath, house has new exterior shingles, new outdoor shower (for the post beach days), new septic. Located in the coveted (and private) Overshores Beach Assoc. Easy access to downtown Madison and I-95. Your idyllic summer awaits!

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.

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

The Carriage House at 43 Soundview Avenue is currently available as an Academic Rental through June 30th 2027. One of Madison's most desirable areas this carriage house offers privacy and a fabulous location. Recently updated with a new kitchen, new floors throughout this rental is sure to delight. The lower level has a stall shower housed within the laundry area and a full bath is on the second level. No Pets and no Smokers. Landlord will pay all utilities.

Furnished academic-year rental in Guilford, Connecticut - a newly built 3-bedroom, 2.5-bath home in a private beach association neighborhood on the Connecticut Shoreline, available September 2026 through May 2027. Turnkey and fully furnished: arrive with a suitcase. The open-concept main level features a renovated kitchen with quartz countertops, an oversized center island seating three, stainless steel appliances, vented range hood, and light shaker cabinetry, opening to a living room and a dining area that connects to a glass-walled sunroom overlooking the yard. A second sunroom upstairs and a dedicated office off the landing offer two quiet work-from-home spaces. The upper level includes the primary bedroom, two additional bedrooms, and a full bath with soaking tub, separate shower, and double vanity. Central air, recessed lighting, ceiling fans, wide-plank vinyl floors, and a main-level half bath complete the home. Beach association rights put Long Island Sound, Jacobs Beach, and the Guilford marina minutes away, with Guilford Green, Boston Post Road dining and shops, and the Guilford Shore Line East train station to New Haven all close by. A low-maintenance, move-in ready base for visiting faculty, graduate students, or professionals on assignment who want the Connecticut Shoreline without the commute.