luxury properties for rent Old Lyme, United States

Rarely available! This historic 1860 Essex Village waterfront home is nestled on a quiet lane with direct waterfront on Middle Cove. Step back in time and experience the charm of this Vintage home, complete with many original features, while still enjoying modern amenities and updated appliances. The home boasts original wood floors, a stunning floor-to-ceiling bay window in the living room, and a built-in hutch with a Butler's Pantry in the dining room. Upstairs, the primary bedroom is a spacious two-room suite, accompanied by an additional bedroom and bath. The semi-finished lower level, reminiscent of a cozy tavern room, provides walkout access to the patio, backyard, and waterfront. View stunning sunsets over Middle Cove! Relax on the inviting front porch or take a short stroll to the Griswold Inn, Noah's, the Black Seal, and an array of charming shops, yacht clubs, and marinas. The barn outbuilding is not included in the rental. No pets, no smoking. Minimum 1-year lease. Conveniently located halfway between New York and Boston. You will love living in one of the Historic Homes of Essex Village!

Live the Good Life in Historic Essex Village! This beautifully renovated 3 level apartment in an 1880 duplex home blends timeless charm with modern design in the heart of the Connecticut River Valley. Thoughtfully reimagined with an architecturally designed open floor plan, the light-filled first floor features soaring 9+ foot ceilings and generous spaces for living, dining, and entertaining. The stylish kitchen boasts stainless steel appliances, granite countertops, and crisp white cabinetry. A full bath completes the main level. Upstairs, the private primary suite offers a serene retreat with its own full bath, dressing area, and a wall of closets. The third floor provides flexible space-ideal for a home office or storage. Comfort is ensured with split-unit AC/heat on all levels and efficient oil-fired hot water heat on the first and second floors. Laundry is conveniently located in the basement. Relax on your private backyard patio. Just steps from your front door, enjoy Essex's unique shops, fine dining, scenic marinas, and the beautiful Connecticut River. Perfectly situated midway between New York and Boston, this is Village living at its very best!

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.

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.

A Timeless Summer Tradition: Renovated Victorian Shingled beach house in the Borough of Fenwick Experience the quintessential New England summer in the historic Borough of Fenwick. This stunning, shingle-style Victorian beach house seamlessly blends old-world coastal charm with modern, high-end luxury. Featuring 8 spacious bedrooms and 4.5 baths, this expansive residence is the perfect sanctuary for large families or those who love to entertain against the backdrop of the Long Island Sound. The heart of the home is a totally renovated gourmet eat-in kitchen, designed for the culinary enthusiast and large-scale hosting. Beyond the kitchen, life slows down on the magnificent wrap-around screened porch-the perfect vantage point to enjoy your morning coffee or an evening cocktail while overlooking the water and catching the sea breeze. Retreat to the third floor, where a dedicated playroom offers a private escape or a quiet workspace away from the main living areas. From its cedar-shingled exterior to its thoughtfully updated interior, every inch of this home invites you to relax, recharge, and rediscover the magic of a Fenwick summer.

Academic rental located in the charming town of Chester Connecticut. Ideally located for access to nearby colleges including Wesleyan and Connecticut College. This adorable, well maintained home is located just over a mile from the inviting downtown center of Chester with its bustling restaurants and interesting shops. The home has a lovely open floor plan on the main level which includes an updated kitchen with a new induction cooktop range. While preparing a meal you can be engaged with those in the living or dining room through the window like pass through that opens into these spaces. Sliders from the living and dining room open onto the rear yard and patio. Enjoy relaxing outside or fire up the grill and prepare dinner. Also on the main floor is a half bath and plenty of storage. Access the second floor by climbing the coolest oak spiral staircase. Enjoy a large primary bedroom with ensuite bath and ceiling fan. The second bedroom is just down the hall past the hallway bath. The laundry room is conveniently located in this bathroom. The yard is generous and private. The dates of occupancy are September 1- May 31(possibly through June 30). The use of the wood stove will be considered by the landlord.

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!

AVAILABLE FOR THE MONTH OF JUNE. 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 THE MONTH OF JULY. 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 THE MONTH OF AUGUST. 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 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.

Enjoy the best weeks of summer in Madison in this exceptional, academic rental! Available August 10th, this beautifully-crafted residence offers the ideal blend of comfort and tranquility, just minutes from the shoreline and town center. The thoughtfully designed interior features a welcoming living room with gas fireplace, creating an inviting atmosphere for evening reading or entertaining family and friends. The well-appointed kitchen with custom cabinetry and granite countertops flows seamlessly into a charming dining area -perfect for hosting gatherings or quiet meals.The dedicated den/office provides an ideal space for working from home. A convenient half bath with laundry room completes the main level. Upstairs, the primary suite is a peaceful retreat with a full bath, complemented by two additional bedrooms and another full bath. The basement is partially finished providing the possibility for an in-home gym, recreation room, secluded office, additional storage space or all of the above! The private, fully-fenced backyard sanctuary features a stunning bluestone patio and custom wood-burning fireplace, offering a serene environment for outdoor relaxation, and the two-car, detached garage adds practical convenience. This property is the perfect setting for professional pursuits while maintaining access to coastal amenities and a plethora of commuting options. With so much to offer, make sure to view 41 Liberty Street today!

Embrace the serene beauty of Middle Beach with this exquisite academic rental, available from September 15th through May 15th, 2027. This direct waterfront property offers a tranquil retreat with open-concept living and breathtaking views of the water. The main level is designed for comfort and elegance, featuring a cozy gas fireplace, an updated kitchen with modern amenities, a convenient dry bar, and the first of three full bathrooms. As you ascend to the second level, you'll find four well-appointed bedrooms and two additional full baths, ensuring ample space to comfortably accommodate six guests. Wake up to the soothing sights of the shoreline in the primary bedroom, which boasts panoramic water views, a spacious walk-in closet, and an en-suite bathroom equipped with a stall shower and double sinks. The third floor unveils a hidden gem: a deck and office nook that present the ideal vantage point for witnessing the captivating sunsets that Middle Beach is known for. This space provides a peaceful haven for work or relaxation, enveloped by the natural splendor of the coast. While some pets may be considered, please note that cats are not permitted. This property is a rare opportunity to experience coastal living at its finest during the fall, winter, and spring months. Don't miss the chance to call this waterfront haven your temporary home.

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.

Authentic 1770 Cottage in the heart of Orient Village. Lovingly restored & maintained Village home on beautifully landscaped lot, offering private grounds & distant views of sunsets over the bay. Furnished in period antiques, screened-in porch off kitchen, first floor bedroom. Walk to amenities, bay beach, Yacht Club, marina, farm stand & Jitney. Offered Sept 3-Oct 3 for $8,000. Permit #0091.

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.

Impeccably restored 19th Century gem located in the heart of Orient Village with bay views. Close to bay and sound beaches, and a stroll to all village amenities. Featuring 2 parlors, 3 bedrooms, library, office, eat-in kitchen, updated baths, charming garden, out-door dining, and grill, out-door shower. Offered April $6,000; May $6,000; June $15,000; Sept $12,000. Permit #0483.

Charming historic Bayfront beach cottage located on Orient Harbor in Orient Village. Featuring 75 feet of private walkout beach, waterside porch, screen bay view gazebo for entertaining. Interior includes wide plank wood floors, renovated baths, spacious kitchen water view living room with wood burning fireplace, 2 ensuite bedrooms for a total of 3 bedrooms/ 2.5 baths. Walk to Country Store, Post Office, Orient Yacht Club, marinas, and other village amenities. Close to renowned Orient Beach State Park & Cross Island Ferry. Available Aug $35,000. Permit# 1374. No showings until after January 15, 2026.

6 WEEKS OF BLISS!! THINKING OF RENTING A CHARMING HOUSE IN MADISON FOR THE SUMMER? Available from July 19, 2026 to August 30, 2026. The Landlords are seeking a renter to take the entire term (no weekly or 2 week rentals available). Called The Wendell Farm, this 3 bedroom home has a chef's kitchen, hardwood floors, open floor plan, and newly added Master Suite in 2008. Spectacular Madison Beaches are a 5 minute drive away. Downtown Madison is 3 minutes away. The public middle school across the street, Polson Middle School, has tennis courts and playing fields. The property is complete with the quintessential red barn. Come experience the easy summer lifestyle in Madison. Landlords and house are pet friendly. Tenant pays for electricity.

DIRECT WATERFRONT with unobstructed views of Long Island Sound. LIFE IS BETTER AT THE BEACH. Available for the month of June. Amazing home to gather with friends and family offering large open floor plan, 5 bedrooms, large 3rd floor rec room, porch for al fresco dining...Don't feel like cooking? Head over to the Madison Beach Hotel & treat yourself to cocktails, lunch, dinner with amazing views. Life is Short...Enjoy Madison at its finest.