Middlesex County Vacations & Trips from $374

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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

The Latest Middlesex County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex
Beechmont - Perfect for Family Retreat!
Landing Apartments New Haven Near Dixwell
Hyatus Luxury Residences City Crossing
New Haven Hotel

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

Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
$264 nightly
The price is $304 total per night from May 25 to May 26
$304 total
May 25 - May 26
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
"Nice location, well maintained grounds, the buildings are old, old bathrooms, not well controlled temperature in the guest rooms, some of the staff is not very welcoming."

Reviewed on May 23, 2026

Water's Edge Resort & Spa
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundable
$98 nightly
The price is $112 total per night from Jun 7 to Jun 8
$112 total
Jun 7 - Jun 8
Total with taxes and fees
8/10 Very Good! (1,004 reviews)
"Comfortable for a nights stay. Close to nice restaurants and shopping."

Reviewed on May 21, 2026

Pier Blue Inn Old Saybrook - Essex
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

2 out of 5
298 E Haddam Moodus Rd East Haddam CT
$175 nightly
The price is $201 total per night from Jun 23 to Jun 24
$201 total
Jun 23 - Jun 24
Total with taxes and fees
9.6/10 Exceptional! (154 reviews)
"Nature path"

Reviewed on May 23, 2026

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.