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
• UPDATED HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge
• Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults
• Spacious yard and view of Long Island Sound- walk to secluded beach!
• Autumn and Winter at the Haddam House
• Waterfront Escape
• COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
• You and your Family deserve a break. Relax and enjoy lake front living

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
• Charming Old Saybrook Cottage Less Than 1 Mi to Beach
• Cottage-Chic Retreat Less Than 1 Mi to Connecticut River!
• Charming Westbrook Cottage, Steps to Private Beach
• Remodeled 4 BR Waterfront Beach House with all the Comforts of Home.and more!
• Saybrook Manor Beach House
• New England Tiny Home Experience: Coffee & More!
• Relaxing summer rental, walking distance to the beach, short ride to the outlets

Yes, there are 7 self-catering vacation homes in Middlesex County that have hot tubs, swimming pools, & other amenities.

There are more than 7 luxury villas and vacation homes in or near Middlesex County. Filter by price to compare find the most expensive places to stay on Marthasvineyardcottages.

Yes, there are 7 pet friendly vacation homes and places to stays that are available in or near Middlesex County that you may consider.