37 houses for rent in Old Saybrook town

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

Remodeled in 2026 with new siding, front doors, carpeting, Pergo, soft close cabinets, counter tops, rangeoven, hood, close to town beach, 1st floor, one off street parking space. Owner takes care of lawn and yard maintenance, heat and hot water. Tenant pays cableinternet, electricity, no pets and no smoking. Get the best price at ListedBuy!

Annual Furnished Rental. Nestled in the heart of one of Madison's most sought-after beach communities, this charming and meticulously maintained home offers an effortless coastal lifestyle just moments from Overshores Beach. Thoughtfully furnished and move-in ready, the home features a welcoming floor plan with a sunny kitchen, comfortable family room, classic living room, home office, powder room, and delightful three-season porch perfect for enjoying summer breezes. Upstairs are two generously sized bedrooms and a full bath. The kitchen blends vintage character with modern convenience, featuring stainless steel appliances and timeless appeal. Whether you're working remotely from the dedicated office, relaxing with a book on the porch, or taking a short walk to the beach, this home is designed for easy living. Fully furnished and equipped with linens, kitchen essentials, beach towels, and chairs, this turnkey rental offers everything needed to enjoy life on the Connecticut shoreline.

Coastal Gem! Furnished Winter Rental Just Steps from the Beach Available September 14, 2026. May 15, 2027 Escape to this beautifully updated one-level home just a short walk from the beach! Fully furnished and thoughtfully designed for easy living, this 3-bedroom, 2-bath rental is the perfect off-season retreat. Enjoy a modern kitchen with granite countertops, double ovens, a cooktop, and plenty of storage-ideal for cooking cozy fall and winter meals. The spacious living room and open-concept kitchen/dining area offer room to relax and entertain. A 3-season sunroom with its own shower and changing room (seasonal) opens to a large, private double lot-perfect for enjoying crisp mornings or sunny afternoons. Highlights You'll Love: Fully furnished, move-in ready 3 bedrooms, 2 full baths. All on one floor Stylish, updated kitchen with granite & double ovens Sunroom with outdoor shower/changing area Large, grassy yard

Academic Rental October 1, 2026. May 31, 2027. Charming 3-bedroom, ranch-style home in the Harbor View Beach Association. Large living room, 3 generous bedrooms, updated kitchen and bath just steps to the association beach

The sweet little yellow house on historic Grove Street. Stroll to all Essex Village offers; walking trails, restaurants, library, post office, marinas, yacht clubs, boutiques and more. This is the perfect perch to explore and enjoy the Connecticut River Valley and Shoreline. Home consists of 2 bedrooms, a full bath, laundry in the walk out basement, a great farmers porch and a spot for gardening. Furnished rental. Flexible terms. Six month minimum and one year maximum rental period

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 uni

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. Convenien

Academic furnished rental in White Sands Beach. Large living room with fireplace, dining room with table for eight, fully applianced kitchen, sunroom/office, laundry and full bath all on the first floor. The four bedrooms and newly updated hall bath are upstairs. Cable and wi-fi installed. Across the road are a tot lot, basketball court and large open space for other games. A short walk to the Association beach. New hardwood floors installed upstairs. Rental start date is September 1

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 ent

Immaculate Greenport rental with saltwater pool! Conveniently located while also ideally set in a quiet enclave, this home is just a stone's throw to a sandy Bay side beach as well as a Sound beach and offers the best of both worlds. A spacious kitchen and family room create seamless everyday living and entertaining. There is also a first-floor bedroom and full bath which are perfect for separate sleeping accommodations. Sliding glass doors from the family room provide access to an outdoor retreat where there is a dining and poolside lounge area. The second floor offers another living areau002Fden, a full bath and two light-filled bedrooms. Including a primary ensuite with Juliet balcony and the second bedroom with a fireplace. A recreationu002Fmedia room complete with laundry, a full bath and outdoor access can be found on the beautifully appointed lower level. Don't miss an opportunity to enjoy the North Fork and all it has to offer with this amazing rental. Permit #: 0384. Price ref

This charming 2-bedroom has been recently painted throughout, it features an inviting atmosphere with fresh, neutral tones that brighten every room. The home includes an additional smaller room that can easily be transformed into a playroom, office, or additional storage space. Ideal for a variety of needs. Step outside and enjoy a spacious yard, perfect for outdoor activities, gardening, or simply relaxing. The back deck provides a private retreat for morning coffee or evening relaxation, while the front covered porch adds charm and curb and invites you to sit down and watch time go by. In a peaceful corner of town, this home is just steps away from the playground and sports fields at Caulkins Park, providing easy access to outdoor recreation. Whether you're looking for a quiet neighborhood or a location near community amenities, this home has it all