luxury furnished houses for rent Old Saybrook, United States

ACADEMIC RENTAL SEPTEMBER-JUNE . . . Charming Four Bedroom New England Contemporary Colonial with Beach Rights. Discover the perfect balance of relaxation and accessibility in this vibrant academic rental. Nestled in a picturesque New England setting, this home is designed for those who love to get out and explore. Start your morning with a stroll to Julie's Cup of Joe for coffee or enjoy your weekends utilizing your private beach rights. The home features 4 spacious bedrooms, 2.5 bathrooms and a layout that is perfect for entertaining indoors or outdoors. Whether you are hosting friends or settling in for a quiet evening, this property offers the ultimate convenience. Don't miss your chance to live in one of the town's most desirable locations!

Ideal academic rental offering comfortable shoreline living from September through early summer. Steps to nearby private or town beaches, then head home to study or unwind in the light-filled sunroom. The open main level features a custom kitchen overlooking a charming living room with a gas fireplace, dining space, and sitting area. Enjoy easy main-floor living with a first-floor primary suite. Minutes to local shops and dining!

Direct Waterfront in desirable Harbor View Association with your own private dock! Amazing unobstructed sunset views in this 3 bedroom Ranch style home with 2 car garage. Steps to the Private Association Beaches and Clinton Town Beach! Set on a double lot that goes to the water, leading to your own private dock where you can fish, crab, kayak, or boat ride out to the open water of Long Island Sound in less then 5 minutes.

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.

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.

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.

Welcome to 12 East Bishop St. This academic rental is available from October 1, 2026 thru May 31, 2027. This well maintained home has 3 bedrooms, one of which is on the first floor. The first floor also holds the beautifully updated eat-in kitchen with granite counters and stainless steel appliances, living room, sunroom, and a full bath with shower stall. On the second floor you will find 2 additional bedrooms and another full bath. A washer and dryer are provided for tenant use in the basement. This home is located within 5 minutes of Niantic where you can enjoy the boardwalk, beaches, shops, and restaurants. It is also within 20 minutes of Electric Boat/General Dynamics, the Coast Guard Academy, and L&M Hospital. NO Pets and NO smoking. Tenants are responsible for heat, hot water, electricity, liability insurance, snow removal, and cleaning fee of $350.

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

2026 Rates: April $7,500; May $12K; June $15K; July $25K; A1-LD $27,500; Sept $12,500; October $10K: This beautifully curated home away from home, blends modern design with warmth and style. Experience elegant comfort in your private retreat with natural light, modern decor and thoughtful touches throughout. Nestled on a quiet, tree lined street, this special haven features a front porch, fully equipped open kitchen, and spacious backyard with a pool and fire pit. Enjoy all season living in this home away from home just a 10 minute walk to The LIRR station, Hampton Jitney, and The North Ferry.

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.

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.

Modern design meets coastal enchantment. A beautiful waterfront retreat, built partially over the water in the coveted Shelter Island Heights enclave. This modern boathouse-style home, c.1920, offers 3 beautifully spaced bedrooms, including one with a mesmerizing glass-bottom floor revealing the harbor below, and 3 bathrooms. Meticulously renovated by its designer-owner, the home exudes a refined nautical spirit with soaring ceilings, natural textures, and panoramic water views create a sense of calm and inspiration throughout. Outdoor living features two decks, including one with a cedar hot tub overlooking Dering Harbor. Additional highlights include a sauna, outdoor shower, and a vintage Airstream trailer. A floating dock accommodates boats (30" depth at low tide). Residents enjoy access to community tennis courts and a private beach club, with nearby golf, beaches, nature preserves, trails, shops, restaurants, markets, and hotels. The Shelter Island Yacht Club is close by, and convenient transportation-including boat rentals, the North Ferry, Jitney, and train-makes travel between NYC and the North and South Forks effortless. High-end appliances, fine linens, bicycles, and beach essentials are provided for a seamless, elevated stay. A wonderfully inspired waterfront haven-modern, magical, and truly unique. [[Rental Registration # #L-0009]] EH RR #: # L-0009 Rental Terms: July: $70,000 September: $70,000

Stunning new modern home with an abundance of natural light throughout. 4 bedroom, 3 bath home with plenty of room for your loved ones. Home has a large open living space with oak floors and high ceilings with huge Anderson doors that opens onto extensive covered deck for seamless indoor outdoor entertaining. Two guest bedrooms and a bathroom complete the first floor. The master suite is on the second floor with a balcony to enjoy morning coffee, a walk through closet, and bathroom with free-standing soaking tub and large shower. The lower level has with sealed concrete floors with underfloor heating, a spacious living/ den area, office space, bedroom, bathroom and laundry room and separate entrance. Great yard with mature Japanese maple tree, birches and hedging. Please call with any questions or to set up an appointment to view. [[Rental Registration # 2025-L-0061]] EH RR #: 2025 -L-0061 Rental Terms: August - Labor Day: $30,000 Memorial Day - Labor Day: $62,500 August: $22,500 July - Labor Day: $47,500 July: $22,500

Summer is here, and this home has vacation written all over it. Enjoy spectacular sunset water views of the Long Island Sound from the spacious wrap-around deck or from the bright, open-concept living spaces inside. Perfect for entertaining, the layout features 4 bedrooms and 2 full bathrooms, offering a beautiful oasis for relaxation and togetherness. The lifestyle here is effortless: Kenny's Beach access is just steps away (.02 miles) for swimming in the Sound, complemented by a refreshing outdoor shower back at the house. Plus, you can leave the car behind and stroll down the road (.03 miles) to grab lunch or dinner at the hot new local restaurant, Little Fish. Let's get you set up in the perfect summer getaway—inquire today! Availability: June 15-June 30th $10K | July $35K | August $30K

Beautifully renovated and furnished and now ready for its first tenants. This lovely two story home is your perfect retreat. A wonderful location close to Wades Beach, The South Ferry, and the 2,350 acre Mashomack Park and Preserve. The house sits on a 1.13 landscaped acre property complete with a heated gunite pool, pool house, outdoor shower, and spacious entertainment patio. The tranquil elegance of this home is visible everywhere, from the welcoming entry foyer to the living room and formal dining room. Enjoy the bright well appointed kitchen with access to the outdoor patio and a comfortable lounge area. Upstairs there are three guest bedrooms, a full bath and a spacious ensuite principle bedroom. This property is the newest project of Eldon Wong, a respected designer who has reinvented houses throughout the Hamptons area. His talent is showcased in this property. A great combination of comfort and high design. [[Rental Registration # 2025-L-0135]] EH RR #: 2025-L-0135 Rental Terms: June: $15,000 Memorial Day - Labor Day: $70,000 July: $25,000 August - Labor Day: $40,000

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.