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
Old Saybrook
The Latest Middlesex County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
Price was $499, price is now $374 per person
$374
per person
Jul 24 - Jul 26
found 7 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
8/10 Very Good! (1,001 reviews)
Comfortable for a nights stay. Close to nice restaurants and shopping.
Reviewed on May 21, 2026
Hyatus Luxury Residences City Crossing
The Hill
Price was $1,507, price is now $1,195 per person
$1,195
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.2/10 Wonderful! (31 reviews)
Great stay with many amenities to enjoy within the building!
Reviewed on Apr 3, 2026
New Haven Hotel
Downtown New Haven
Price was $791, price is now $664 per person
$664
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.2/10 Wonderful! (2,139 reviews)
The complimentary coffee was much appreciated. The staff were so great and helpful, and genuinely want your stay to be as perfect as possible. One thing that was repeatedly bothersome, even at 7:00 a.m., was the overly loud music in the back of the lobby area, and it was not calming music, it was loud dance music and a style of music that does not appeal to all audiences. It would be much more pleasurable if it was half the volume and a mix of music genres so all guests can feel more comfortable. The volume made it difficult to relax and get work done. Everything else about our stay was great.
Reviewed on May 22, 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
Water's Edge Resort & Spa
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
Pier Blue Inn Old Saybrook - Essex
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
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
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
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
