67 properties for rent in Old Saybrook town

Gorgeous Restored 1815 Colonial. Annual Rental available starting 12/19/25 Dogs Welcome! This beautifully restored 1815 colonial shows like new construction while preserving its classic New England character. Set on a level 1.65-acre lot close to beaches and all downtown Old Saybrook amenities, the home offers the perfect blend of historic charm and modern luxury. High ceilings, sun-filled rooms, and tasteful finishes create a warm, elegant living environment. The chef's kitchen is a standout, ideal for those who enjoy cooking and entertaining. The home is offered fully furnished and turnkey for immediate ease, but the landlord is willing to rent unfurnished if preferred. The expansive grounds provide rare space and privacy, ideal for outdoor enjoyment in any season. Up to two dogs are allowed with permission; no cats. This is a unique opportunity to enjoy an impeccably restored historic home in one of the shoreline's most desirable coastal towns-minutes to beaches, marinas, village sh

Waterfront, beautifully appointed luxury home on South Cove off of Long Island Sound. There are spectacular water views from the main living area, kitchen and Master Bedroom Suite. Two guest bedrooms are in separate wings of the house with private entrance and private, covered porch. Fully equipped and furnished, Wi Fi, cable, gourmet kitchen, dining room, large living room with stone fireplace. Master Suite with king bed, large master bath and private outdoor deck overlooking the Cove and views of sunrises, sunsets and wildlife. First guest bedroom has king bed and private bathroom. Second guest bedroom, with ensuite bath, has twin beds. Private kayak dock on property includes use of two kayaks. Lower level fully equipped fitness room with flat panel TV. Covered screen porch on one side of the house and large stone patio with a fire pit overlooking the cove on the other side. The home setting provides a quiet and relaxing environment. Association beach is a short walk away. Enjoy near

{Summer 2025} This beautiful property is a direct waterfront, 4 bedroom, one-level home situated on a sandy beach in a private association. Wake up every morning to ocean waves, and watch the panoramic sunrises and sunsets which are magical here. Upon pulling into the driveway, you'll be greeted by breathtaking water views. The expansive patio right on the beach is perfect for entertaining or relaxing, and is just a few steps to the water. Enjoy spending days taking long walks, running, seashell collecting, swimming, grilling, entertaining, and making priceless memories. Inside, this beach home offers: stunning ocean views, high ceilings with fans, a wall of windows with sliding door, central air, recessed lighting, New England style light and bright design, open concept one-level living, ample closet space, laundry, 4 bedrooms (king bed in master), and 2 full baths. The kitchen is complete with granite, stainless steel appliances, and a large island with breakfast bar. Recent home upg

3 Bedroom, 2 Bathroom Apartment For Rent. 1344 Sqaure Feet. $3150/Month, $3150 Deposit. Additional Storage|Storage Space|Dish Washer|Hardwood Flooring|Sundeck|Wireless Internet|Yard|Updated Bathroom|Updated Kitchen|Central Air|Stainless Steel Appliances|Water Included|Laundry In Building. 4 Old Colony Rd, Old Saybrook, CT 06475

Step into this delightful and charming fisherman's cottage in the heart of downtown Old Saybrook. Built in 1800, 43 Pennywise Lane blends warm and cozy character with surprising spaciousness. The owner has preserved this home's historical integrity while adding in modern comforts. The first floor features an oversized primary suite with full bath, office space and reading nook. The eat-in kitchen is highlighted by gleaming wood counters and a beautiful decorative fireplace. Rounding out the first floor, you'll find the sun filled napping corner, a tucked away charming TV area and a second full bath. You'll also appreciate the mini-mudroom drop zone perfect for your bags, boots and hats! Upstairs you'll find an additional bedroom and a second media or lounge area. This space is ideal for guests or a quiet place to unwind. Enjoy the convenience of an outdoor shower, grill, fire pit and the nicely sized, partially fenced in yard. Fancy a stroll to town? It's just down the block with terri

Step into this delightful and charming fisherman's cottage in the heart of downtown Old Saybrook. Built in 1800, 43 Pennywise Lane blends warm and cozy character with surprising spaciousness. The owner has preserved this home's historical integrity while adding in modern comforts. The first floor features an oversized primary suite with full bath, office space and reading nook. The eat-in kitchen is highlighted by gleaming wood counters and a beautiful decorative fireplace. Rounding out the first floor, you'll find the sun filled napping corner, a tucked away charming TV area and a second full bath. You'll also appreciate the mini-mudroom drop zone perfect for your bags, boots and hats! Upstairs you'll find an additional bedroom and a second media or lounge area. This space is ideal for guests or a quiet place to unwind. Enjoy the convenience of an outdoor shower, grill, fire pit and the nicely sized, partially fenced in yard. Fancy a stroll to town? It's just down the block with terri

Summer 2026. Available: June 15-30 for $9,000. Rented: July/Aug/Sept. This beautiful property is a direct waterfront, 4 bedroom, one-level home situated on a sandy beach in a private association. Wake up every morning to ocean waves, and enjoy the panoramic sunrises/sunsets which are magical here. Upon pulling into the driveway, you'll be greeted by breathtaking water views. The expansive patio right on the beach is perfect for entertaining or relaxing, and is just a few steps to the water. Enjoy spending days lounging on the beach, taking long walks, running, seashell collecting, swimming, entertaining, and making priceless memories. Inside, this beach home offers: stunning ocean views, high ceilings with fans, a wall of windows with sliding door, central air, recessed lighting, New England style light and bright design, open concept one-level living, ample closet space, laundry, 4 bedrooms (king bed in master), and 2 full baths. The kitchen is complete with granite, stainless steel a

WINTER RENTAL available September 15, 2026 through May 31, 2027 for $4,500/month. Enjoy spectacular Long Island Sound views from this beautifully renovated 3-bedroom, 3-bath home in the desirable Knollwood Beach Association. Tucked away on a quiet street just off Maple Avenue and only one street from the beach, this exceptional home offers unobstructed water views and a peaceful shoreline lifestyle. The bright open floor plan features hardwood floors, a custom stone propane fireplace, and a wall of south-facing windows showcasing the Sound. The custom white kitchen offers quartzite countertops, a porcelain farmhouse sink, stainless steel appliances, and a Bosch propane range. The first floor includes a full bath and flexible bedroom or office. Upstairs, the primary suite features cathedral ceilings, a beautifully remodeled bath, generous closets, and water views. A third bedroom, remodeled full bath, and family room open to a covered deck with panoramic views. Additional features inclu

Escape to the serene shores of Long Island Sound with this exquisite summer rental in the coveted Fenwick area of Old Saybrook, Connecticut. This traditional Fenwick Cottage has a harmonious blend of classic charm and modern luxury, making it the perfect waterfront getaway for relaxation and entertainment. Spacious waterside family room featuring a magnificent fieldstone fireplace, creating a warm and inviting atmosphere for family time or quiet contemplation. A large, beautifully designed chef's kitchen with top-of-the-line appliances, an inviting eating area, and a wet bar, catering to culinary enthusiasts and effortless hosting. Expansive covered wrap-around porch with a cozy outdoor fireplace and a luxurious hot tub, perfect for evening relaxation or social gatherings. There is an elevator off the kitchen. This Fenwick summer rental is not just a home; it's a retreat that promises unforgettable moments and tranquility amidst the natural beauty of the shoreline. Whether you're baski

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

List price is per week. Inquire about available dates. Are you traveling for business or pleasure or need a temporary place to stay while work is done on your own home? If so, then this cottage. 1 mile from Town and beaches. Might be just the ticket! FULLY RENOVATED in 2021, this furnished, open concept cottage combines the living room, kitchen and dining area and has a separate bedroom and full bath. Walk/bike to downtown and beaches; driving takes under 5 minutes. Amenities include 2 split HVAC systems; dishes, utensils, small appliances plus oven/stove, microwave, dishwasher, full-size refrigerator, washer and dryer; linens and towels. Discover the world-renowned R.J. Julia Booksellers, Madison Art Cinema, boutiques, farmer's market, cafes and restaurants. Madison is about 2 hours from Midtown Manhattan and Boston and is 18 miles east of New Haven/Yale. With Madison celebrating its 200th birthday there's a lot happening here! (Note: Listing Agent is related to Owner/Landlord)

Available for the month of july 2026. Seeking a 4 bedroom fully furnished summer 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

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

Academic year rental in the coveted Buffalo Bay private beach association with direct private beach access just steps away. This classic Madison home offers a bright, welcoming layout with spacious living areas, comfortable bedrooms, and a wraparound porch ideal for quiet mornings or evening relaxation. Located just minutes from Madison's downtown, shops, restaurants, and schools, with convenient access to I-95 and Route 1 for an easy commute. Yale University and Yale New Haven Hospital are within comfortable driving distance, making this an ideal academic or medical-year residence. Available for academic year rental beginning Sept 2026. Enjoy peaceful shoreline living with exceptional convenience

Nestled in the charming New England town of Madison, CT, this contemporary ranch home offers a spacious and comfortable summer retreat. With 4 bedrooms & 3.5 baths, this home comfortably sleeps up to 12 guests, making it perfect for a large family or group of friends. Located just a short walk or bike ride from the town center & Madison's beautiful beaches, the house features a large private yard with an inviting inground pool, providing the perfect place to soak up the sun, or rest in the shade on a bench or hammock. Inside, the home boasts modern amenities and stylish decor, with an open floor plan that seamlessly connects the living and dining areas. The fully equipped kitchen includes all the comforts of home with plenty of counter space for preparing meals, while the comfortable living room features large windows that flood the space with natural light & garden views. At the front of the house the entertainment room offers pool table, ping pong table and large screen TV. Madison i

Exciting news! This absolutely darling academic rental is unexpectedly available as Tenant had a change in plans. Fully furnished 1 bedroom 1 bath carriage house apartment available for rent SEPTEMBER 2025. June 2026. This 2nd floor unit overlooks a beautifully manicured backyard and features a private entrance and ample off street parking. Enjoy the walk to beach and downtown as this rental is prime location here in Madison! Completely renovated with modern fixtures, the'Upper Deck' is one of the prettiest and well kept rentals. Kitchen is updated with modern finishes and opens to the living / family room area. The bedroom is nicely sized with a queen bed and ample closet space. The full bath has been renovated and features a stackable washer dryer. This rental does not last! Landlord covers snow removal, lawn care, trash, WIFI and Cable. Tenant covers for electricity and water. No smoking. EXCELLENT credit required. Ideal only for single person or couple based on septic size. Two mon

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

Beautiful Views, Access to Semi Private Beach. Close to Wineries, Farms Restaurants, Ferries to Connecticut and The Village Of Greenport. Available Sept 2026. May 2027. Rental Permit Pending

Available June $25,000; July 1-23 $27,000 (RENTED); Sept 9-30 $18,000. Bright and spacious Contemporary summer rental on the North Fork. Featuring floor to ceiling windows, great room, 6 bedrooms, 3.5 bathrooms, eat-in kitchen, recreation room. Private back yard with 40x20 salt water heated pool. Permit #1230

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!

Available for month of august. Relax and unwind for a summer at the beach. This well maintained, 3 bedroom home with vintage beach house charm, has easy access to a private association sandy beach just steps away. The open Living Room and Dining Room with the original wood floors are adjacent to a well equipped and modestly updated kitchen for all of your food preparation needs. There is also a mudroom off the kitchen which includes a shower with hot and cold water, making it easy to rinse off when returning from the beach. A Ductless AC system cools off the whole house. The 2nd floor has three bedrooms. One king (master), one full and one with 2 twin beds plus a full bath with shower. A wonderful, expansive front porch, with screens, is a great place to entertain or read. The spacious back and side yards are perfect for all types of summer games and provide a clear view down to the water! The 2 car garage is perfect for storing lawn chairs and beach gear (provided), as well as bikes.

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 basem

Beautifully Renovated Greenport Village Farmhouse with Bay Beaches, NYC Transportation, Village Shops and A Marina Nearby. Summer 2026. July $14,000; August to Labor Day $17,500. Permit#25-018

Available for the Month of August. 8/1/2026 to 8/31/2026. This home usually goes REALLY FAST because of it's outstanding location and the amenities it offers. Enjoy a summer vacation in an impeccably maintained 4 bedroom, 2 full bath and one 1/2 bath home that is beautifully furnished and fully stocked for all your needs. Central air-conditioning. Located steps to West Wharf Beach and the Madison Beach Hotel. Walk or bike to downtown Madison or the other beautiful beaches located in town. Just bring a towel, sunscreen and a toothbrush! Enjoy making beautiful memories during the Summer of 2026. Tenant is responsible for any CT Short Term Rental tax based on the length of their lease

Greenport waterfront condo. Enjoy your life in this well. Appointed Bayfront 2 bedroom, 2 bath condo with stunning views of Shelter Island and Greenport Harbor. Amenities include a waterfront pool, tennis & pickle ball court, 200 Ft of private sandy bay beach, and your own boat slip in the private marina. Located just a short distance to shops and restaurants in Historic Greenport Village, ferry to Shelter Island for fun day trips and the Hampton Jitney or the LIRR train offer easy access to and from NYC. Everything you need is right here. July, august, september 2026 are rented. Available October 2026 $4,500. Off season November 2026 through April 2027 $3,350 per month. May 2027 $4,500, August 2027 $13,000. Greenport rental permit #26-106