Owner Direct Vacation
Rentals in Old Saybrook

There are a lot of options in Old Saybrook. If you plan on staying in the Old Saybrook area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Old Saybrook:

• Waterfront Retreat overlooking Long Island Sound w/gorgeous sunrises & sunsets!
• Saybrook Point Cottage - Charming and Private
• Wake up with Views of the Ocean
• Luxury Waterfront Home-Still some availability for Summer 2026
• The Homestead
• Birdsong - Relaxation, Activities & Culture In Quaint Shoreline Town
• Cozy cottage near downtown Clinton, Marina & Hammonasset Park
• Direct waterfront renovated cottage.
• Cozy Cottage at The Cabins
• UPDATED HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge

There are 14 vacation rentals with private pools near Old Saybrook. Top-rated homes that have access to a swimming pool include:

• Waters Edge Resort and Spa TimeShare
• Charming beach home, complete with pool & cozy guest house!
• Stroll to beach at charming, historical, rustic home w/expansive yard & pool.
• Private Pool! Getaway, 14 Mi to Hammonasset Beach

If you are looking for a family-friendly vacation home in Old Saybrook, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Old Saybrook:

• 2 Mi to Dtwn: 2-Acre Retreat w/Large Yard!
• Wake up with Views of the Ocean
• Westbrook Inn B&B

Currently, the total number of properties listed in 2026 is over 515 in the Old Saybrook area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Old Saybrook.