Middlesex County Vacations & Trips from $570
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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.
New Haven Hotel
Downtown New Haven
Price was $741, price is now $570 per person
$570
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.2/10 Wonderful! (2,115 reviews)
We weren’t happy that parking was $24 a day and that the only part of the breakfast that was free was the coffee. Otherwise, everything else was fine.
Reviewed on May 12, 2026
Luxury Furnished Apartments by Hyatus Downtown at Yale
The Hill
Save 100% on your flight
Price was $1,290, price is now $953 per person
$953
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.6/10 Exceptional! (69 reviews)
I had a great stay at this property overall. The room was clean, comfortable, and well-maintained, which made it easy to relax after a long day. The staff was friendly and helpful, always willing to answer questions and make sure everything was taken care of.
The kitchen was stocked with the basics needed for cooking, which was convenient during the stay. Parking was also easy to access and felt safe, which was a big plus.
The location was convenient, close to nearby attractions, restaurants, and stores. If I had to mention one thing for improvement, it would be minor updates to some areas to make the space feel a bit more modern.
Overall, I would definitely recommend this property and would consider staying here again in the future.
Reviewed on May 5, 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
$264 nightly
The price is $304 total per night from May 20 to May 21
$304 total
May 20 - May 21
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
Great views from the restaurant and bar area. Staff were very friendly and attentive. Will stay here again.
Reviewed on May 8, 2026
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
298 E Haddam Moodus Rd East Haddam CT
$167 nightly
The price is $192 total per night from Jun 11 to Jun 12
$192 total
Jun 11 - Jun 12
Total with taxes and fees
9.6/10 Exceptional! (150 reviews)
Postcards really thought of everything you could want or need for a short stay in the woods. It was exactly what we needed!
Reviewed on May 11, 2026
New Haven Hotel
229 George Street New Haven CT
$121 nightly
The price is $139 total per night from May 26 to May 27
$139 total
May 26 - May 27
Total with taxes and fees
9.2/10 Wonderful! (2,143 reviews)
We weren’t happy that parking was $24 a day and that the only part of the breakfast that was free was the coffee. Otherwise, everything else was fine.
Reviewed on May 12, 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.
