Old Saybrook, CT Houses for Rent

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

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

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

YEAR ROUND FURNISHED OR UNFURNISHED STUDIO RENTAL located in the Ayers Point community with convenient access to I-95 and Route 9. This well maintained and updated studio has the added benefit of INCLUDED UTILITIES (WiFi and/or cable TV are not included in the rent) The main living space features a partial wall that provides separation between the sleeping and living area, creating an open feel

Kara Bell J.M. REALTY

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

Plan now for September to May...Landlord paying all utilities!! Desirable MEADOW WOOD location -----Academic rental available between September 15, 2026 thru May 28, 2027. Wonderful FURNISHED home in cul-de-sac -- 1200 square foot ranch with central air, close to beaches, Peaceful area -- Walk to Dairy Queen, Luigi's Restaurant! One floor living offers renovated, modern open kitchen, dining room,

Lisa Genovali Re/Max Valley Shore

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

Annual Unfurnished Rental in a Prime Location Between Old Saybrook and Essex This spacious and versatile property offers 3 bedrooms and 2 full baths, with 1,826 square feet of main-level living plus an additional 1,120 square feet of finished lower level, complete with a full bath-ideal for extended living, recreation, or workspace. Zoned for both residential and commercial use, this property

Lisa Fekete William Raveis Real Estate

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.

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

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

Rare opportunity --Available June 15 - ANNUAL LEASE! Walk or bike to Saybrook Point or to town! Stunning 3 bedroom Colonial in quaint small enclave of 4 Free Standing condo's with water views is being offered for the first time in years. Fantastic in-town location -- In between North and South Coves, walk or bike to town and Saybrook Point. Hardwood floors, granite kitchen, open floor plan;

Lisa Genovali Re/Max Valley Shore