Old Saybrook, CT Houses for Rent

Great year round rental with 3 bedrooms 1.5 bathrooms, hardwood floors throughout with tiled bathrooms. A large deck with awning overlooking a private back yard. Excellent location, close to beaches, schools and Main Street. Long term tenant would be ideal.

Stephanie Scott Berkshire Hathaway NE Prop.

Available immediatly, if your looking for a place in Old Saybrook to enjoy the summer while your shopping for your forever home great short term rental with water views and plenty of privacy. The best of one level living this adorable ranch has 3 bedrooms and 2 newly renovated bathrooms. Everything is immaculate. This is a great location uniquely situated off of RT one but at the end of a cul de

KD Kling William Raveis Real Estate

2026 Beach cottage -- April 15 to Oct 15 -- $3,500/month. One lucky renter will get to spend spring, summer, and fall in this charming Chalker Beach cottage! Located in a private association, this home is just a short walk to the large soft-sand beach. Walk for miles along adjoining beaches and neighborhoods during the day, and enjoy the magical pastel sunsets over the ocean at night. Inside,

Erika Raffles William Pitt Sotheby's Int'l

A rare opportunity to enjoy this stunning luxury waterfront home located in desirable Cornfield Point Beach. Wake up each day to breathtaking panoramic views and unwind in a beautiful outdoor space designed for entertaining! From the moment you step inside, you'll appreciate the open floor plan, abundance of natural light, and exceptional craftsmanship throughout. Large windows frame the water,

Sharon Linder Berkshire Hathaway NE Prop.

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

Phoebe Schreiner William Pitt Sotheby's Int'l

Adorable 4-bedroom, 1-1/2 bath beachfront retreat available as an academic rental from early September through the end of May in the highly sought-after Chalker Beach neighborhood of Old Saybrook. Offered fully furnished with all utilities included, this charming coastal home that was completely rebuilt in 1986 is the perfect place to enjoy off-season shoreline living. Warm coastal wood paneling

Katie Smith Berkshire Hathaway NE Prop.

Studio unit includes heat, hot water, electricity, cable, and internet. Recently remodeled. Clean and freshly painted. Private bath. Parking available. Conveniently located. Walking distance to beach.

Brian Botti Botti Realty

Classic New England year round beach house across the street from the ocean in the private Knollwood beach area. This home has 4 bedrooms, 2 full baths and an outside shower ! Master bedroom has a king bed, 2nd bedroom has a full size bed, 3rd bedroom has a queen size bed and 4th bedroom has a full and twin bed. Stunning views on every side and amazing sunsets ! This is a great location the

Dawn Caso Williams Realty Services

Fantastic Opportunity to Rent in Fabulous Fenwick! This charming water-view traditional Fenwick Cottage is available from September, 2026, through June 20, 2027! Boasting 4 bedrooms and 4 baths plus a huge third-floor rec room/bunk room space, the home offers over 3,700 sq. ft. of comfortable beach living. Open floor plan living room with walls of windows and French door access to a spacious back

Lynn Lehrman Re/Max Valley Shore

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

Erika Raffles William Pitt Sotheby's Int'l

Turn-key Academic Shoreline Rental for today's modern-living and tastefully decorated in Old Saybrook, CT. Beautifully renovated home in South Cove neighborhood great for morning walks with coffee or evening strolls with a cocktail in hand. This lovely light filled home has an open floor plan, custom built kitchen with modern stainless steel appliances, new hardwood floors throughout, first floor

Terry McDonald McDonald Real Estate, LLC

This spectacular home with a fantastic location is an Academic Rental; from September 15, 2026 through May 15, 2027. Living in this Old Saybrook home is comfortable, near the beach and close to town with shopping and dining. Only a few steps to Cornfield Point, walk the quiet neighborhood and enjoy the gorgeous sunsets. This home is a perfect place of peaceful, tranquil days and evenings, with

Terry McDonald McDonald Real Estate, LLC

BEACHFRONT Beautifully renovated Furnished luxury waterfront $8400 weekly rental or 1200 a day for June 1st thru Sept. 15th or weekly at $8400. Waterviews from all rooms, private beach, plus cornfield point assocation amenties. Enjoy 3 bedrooms all with water-views, 2 full bathrooms, 1 half bathroom, fireplace, CA, new gourmet kitchen, generator, in beautiful seaside setting and neighborhood.

Joel Lucas Coldwell Banker Realty

Amazing views of Long Island Sound at 28 Beach Rd West, Old Saybrook! Beautiful Academic Rental "beach" home, with 3 bedrooms and 2 baths, available for your enjoyment, across the street from Chalker Beach with spectacular and unobstructed views of Long Island Sound. The open kitchen, dining and living room with a gas fireplace are the focal point of the home. The kitchen has gorgeous granite

Terry McDonald McDonald Real Estate, LLC