luxury property for rent Old Lyme, United States

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 terrific shopping and dining. Enjoy all the amenities that make this shoreline town so popular and accessible, including access to Amtrak and the Shoreline East Train. Tenant: renters insurance, heat, electric, water and a one time end of lease cleaning. Landlord: all other utilities. No pets or smoking. A truly special place to hang your hat. July and August 2026. Also available September 15, 2026 - May 31, 2027 for 3K per month.

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 terrific shopping and dining. Enjoy all the amenities that make this shoreline town so popular and accessible, including access to Amtrak and the Shoreline East Train. Tenant: renters insurance, heat, electric, water and a one time end of lease cleaning. Landlord: all other utilities. No pets or smoking. A truly special place to hang your hat. Available September 15, 2026 - May 31, 2027. Also July and August at 6K per month.

Discover 9 Essex Rd (YEAR ROUND RENTAL) a renovated spacious 3-bedroom, 1-bathroom home in beautiful downtown Westbrook. This property features an updated kitchen, modern bath, washer and dryer, and a shared yard. Enjoy immediate access to the town beach, restaurants, Shoreline East train, and I-95. Water and trash removal are included; tenants are responsible for all other utilities. Pets will be considered. Private parking available in the back of the house.

AVAILABLE FOR THE MONTH OF AUGUST. Embrace Coastal Serenity in a Fully Renovated 5 bedroom, direct waterfront Estate WITH ITS OWN PRIVATE BEACH! Discover the epitome of waterfront luxury in this exquisite Clinton, CT residence, where historic charm meets modern elegance. Nestled on a generous .51-acre lot, this multi-level home boasts of a direct waterfront access with plenty of privacy. Built in 1912 and meticulously renovated along the way. Experience the perfect blend of timeless architecture and contemporary updates. A spacious primary suite (with private balcony!) and two additional bedrooms on the second floor, plus two bedrooms and a rec room on the third floor, provide ample space for family and guests. Step outside to enjoy multiple decks with a panoramic view of Long Island Sound and private beach access for tranquil waterfront living. A spacious Living Room with a fireplace, formal Dining Room, light filled Great Room, and a Sunroom offer diverse areas for relaxation and entertainment. This property is a rare gem, offering a waterfront lifestyle coveted by many but enjoyed by few. Whether basking in the warmth of your fireplace or soaking up the sun on your private beach or deck, this home is a sanctuary for those who seek a blend of luxury and tranquility. It's the perfect home for a month retreat!

ANNUAL UNFURNISHED (OR PARTIALLY FURNISHED) RENTAL), AVAILABLE AUGUST 1. 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.

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 FOR ANNUAL RENT. FURNISHED OR UNFURNISHED. 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.

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.

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.

Beautiful renovated 2-bedroom, 2 full bath home in Orient Village. Open concept – living/dining/gourmet kitchen. Lower level with screening room, office, full bath. Walk from Jitney. Enjoy all village amenities, bay & sound beaches. Close to Orient Beach State Park & Cross Sound Ferry. Available April $5,000; May $5,000; June $7,000; July $15,000; Aug $15,000; Sept $8,000. Permit# 1364.

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 months security required.

This in-town house will make you feel right at home with its abundance of charm, comfortable furnishings and bright open floor plan. First floor bedroom and full bath. Eat in kitchen with granite counters and stainless appliances also offers a combination washer/dryer. Sun drenched living room with vaulted ceiling makes cottage space very special. A second bedroom or office space upstairs with an additional half bath. Parking for one car included. Walk to everything Madison has to offer: shops, restaurants, beaches, farmer's market. Can be rented furnished or unfurnished.

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.

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.

July is available at $20,000/mo. August has been rented. Also available for April, May and June at $12,000/mo. Academic available 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!

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 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. The neighborhood is great for taking walks and bike riding. Easy access to downtown Madison by bike or car. Some pets considered.

AVAILABLE FOR MONTH OF JULY. 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. The neighborhood is great for taking walks and bike riding. Easy access to downtown Madison by bike or car. Some pets considered.

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.

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.

STILL AVAILABLE FOR LAST TWO WEEKS OF AUGUST! Panoramic vistas of Long Island Sound and the East River create a breathtaking backdrop for this sophisticated Madison waterfront retreat. Designed for elevated coastal living, the sun-drenched open floor plan flows effortlessly from the main living spaces to expansive water views beyond. Offering 3 bedrooms and 3 full baths, the home comfortably accommodates 8+ guests with thoughtful design and generous gathering spaces. Enjoy easy access to shoreline beaches, perfect for morning swims and evening strolls along the water, while the private heated pool provides a serene setting for long summer afternoons under the Connecticut sky. Available weekly for the last TWO weeks of August at $8,000 per week. A rare opportunity to experience Madison's shoreline lifestyle at its finest - where timeless waterfront beauty meets effortless summer luxury.