
Middlesex County Vacations & Trips from $259
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Middlesex County Vacation
Leave all the planning to us with a Middlesex County vacation package. With everything organized before you leave, the only thing left to do is sit back, relax and experience this destination's countless delights. Begin your trip to Middlesex County with a couple of nights in Old Saybrook visiting popular sights like Westbrook Town Beach and Clinton Crossing Premium Outlets. East Hampton is another city that lures crowds from near and far. TPC River Highlands and Brownstone Exploration & Discovery Park are two of the top places to see here. Expedia is a one-stop shop when it comes to planning your Middlesex County vacation. From accommodations and flights, to car rentals and activities, we're here to help you curate a travel experience like no other.
Top destinations in Middlesex County

Middletown
The Latest Middlesex County Vacation Packages

Sheraton New York Times Square Hotel
Reviewed on Jan 12, 2026


INNSiDE by Meliá New York Nomad
Reviewed on Jan 12, 2026


The Inn At Fox Hollow Hotel
Reviewed on Jan 10, 2026
Find the Best Middlesex County Vacation Packages
Middlesex County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Bradley Intl. Airport (BDL) |
Top Sights | Harveys Beach, Devils Hopyard State Park and Clinton Town Beach |
Middlesex County Hotel Deals

Inn at Middletown
Staff was wonderful, lovely hotel
Reviewed on Jan 5, 2026

Water's Edge Resort & Spa
Great place!
Reviewed on Dec 31, 2025

Pier Blue Inn Old Saybrook - Essex
muy limpias
Reviewed on Jan 8, 2026
Other vacations you might like
- Top cities in Middlesex County
- Vacations and getaways similar to Middlesex County
- Best vacation destinations by month
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
























