Middlesex County Vacations & Trips from $401

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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
New Haven Hotel
Landing Apartments New Haven Near Dixwell
Hyatus Luxury Residences City Crossing
Graduate by Hilton New Haven

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
$347 nightly
The price is $399 total per night from Jul 5 to Jul 6
$399 total
Jul 5 - Jul 6
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
"we stayed for weekend had a great time beautiful room comfortable bed amazing spa tub restraunt food and bar convenient & delicious staff very nice"

Reviewed on Jun 25, 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
$97 nightly
The price is $111 total per night from Jun 30 to Jul 1
$111 total
Jun 30 - Jul 1
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
"staff and parking"

Reviewed on Jun 22, 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
$184 nightly
The price is $212 total per night from Jul 29 to Jul 30
$212 total
Jul 29 - Jul 30
Total with taxes and fees
9.6/10 Exceptional! (160 reviews)
"I stayed here, but there was no lantern or scissors provided, and the lantern in my friend’s unit was broken too. So I asked for a replacement, but I was told there wasn’t one available and to just deal with it. I asked them to help resolve the issue, but all they said was to talk to the manager ..."

Reviewed on Jun 26, 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.

Stay near popular Middlesex County attractions

What to do in Middlesex County

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.