Middlesex County Rentals By Owner

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

• Classic Lake House w/private waterfront, 4 steps to water, FirePit/Kayaks/canoe
• Waterfront Retreat overlooking Long Island Sound w/gorgeous sunrises & sunsets!
• Luxury Waterfront Home-Now booking through Summer 2026
• Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults
• Waterfront Escape
• Marina Guest House
• Cottage at the Marina
• Adults Only Toes In The Sand Beachfront Charmer
• Charming Chester Retreat- Near Village Center
• 3+BR/2 bath in Grove Beach Improvement Association Community. Central AC

There are many large, family-friendly vacation homes available in Middlesex County; however, here are the most popular family rentals listed on our site:

• The Sharlene Cottage
• New England Tiny Home Experience: Coffee & More!
• Remodeled 4 BR Waterfront Beach House with all the Comforts of Home.and more!
• Saybrook Manor Beach House

Yes, there are 368 self-catering vacation homes in Middlesex County that have hot tubs, swimming pools, & other amenities.

There are more than 368 luxury villas and vacation homes in or near Middlesex County. Filter by price to compare find the most expensive places to stay on Trippymates.

Yes, there are 368 pet friendly vacation homes and places to stays that are available in or near Middlesex County that you may consider.