Middlesex County Vacations & Trips from $514
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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
Westbrook
Middletown
Clinton
Cromwell
Essex
East Hampton
The Latest Middlesex County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Landing Apartments New Haven Near Dixwell
Newhallville
$883
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
2/10 (1 review)
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.
Reviewed on May 25, 2026
Hyatus Luxury Residences City Crossing
The Hill
$883
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.4/10 Exceptional! (33 reviews)
The room was spacious and clean. Close to new haven union station, yale university and downtown. We enjoyed the pool, gym and the rooftop. Check in and check out process were very smooth. Sarah was very responsive to our questions. Would def stay here again.
Reviewed on Aug 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
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundable
$99 nightly
$114 total
Aug 19 - Aug 20
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
"Great location & convenient to everything. Shawn (I believe his name was) was so helpful & friendly! Older place but was good for 1 night."
Reviewed on Aug 12, 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
$266 nightly
$306 total
Aug 31 - Sep 1
Total with taxes and fees
8.8/10 Excellent! (1,007 reviews)
"Great staff Multiple food and drink options"
Reviewed on Aug 12, 2026
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
298 E Haddam Moodus Rd East Haddam CT
$215 nightly
$247 total
Aug 18 - Aug 19
Total with taxes and fees
9.4/10 Exceptional! (177 reviews)
"Great property for quiet and a nice getaway. Great little places to eat and shop in the surrounding towns."
Reviewed on Aug 9, 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.
Stay near popular Middlesex County attractions
Photo by Bill Dillard
Essex Steam Train
8.4/10 (165 reviews)
You can spend time browsing the exhibits at Essex Steam Train during your travels in Essex Village. While you're in the area, stroll along the beautiful beaches.
Goodspeed Opera House
9.0/10 (18 reviews)
You can make plans for a show at Goodspeed Opera House during your stay in East Haddam. Wander the riverfront and beaches in the area.
Harvey's Beach
8.8/10 (93 reviews)
If a restful vacation is part of your travel plans, Harvey's Beach might be the perfect place to seek out during your trip to Old Saybrook. Visit the shops and spas in this relaxing area.
Wadsworth Mansion
Learn about the local history of Middletown when you take a trip to Wadsworth Mansion. Experience the area's entertainment venues and festivals.
Wesleyan University
8.6/10 (189 reviews)
Enjoy the collegiate vibe when you visit Wesleyan University, during your travels in Middletown. Experience the area's festivals or attend a sporting event.
Clinton Crossing Premium Outlets
8.6/10 (135 reviews)
You can find the perfect gifts to bring home at Clinton Crossing Premium Outlets during your stay in Clinton. While you're in the area, stroll along the beautiful beaches.
Westbrook Town Beach
8.8/10 (36 reviews)
Why not spend a lazy afternoon at Westbrook Town Beach during your trip to Westbrook?
TPC River Highlands
6.8/10 (22 reviews)
Enjoy a round of golf in Cromwell at TPC River Highlands. While in this family-friendly area, you can savor the top-notch restaurants.
What to do in Middlesex County
Connecticut Coloured Regiment Parade Route: An Audio Tour
$10
per adult
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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.
