Middlesex County Vacations & Trips
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Top destinations in Middlesex County
Clinton
Middlesex County Hotel Deals
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
₩105,888
₩121,771 total
Oct 8 - Oct 9
includes taxes & fees
8/10 Very Good! (1,014 reviews)
"It was a decent stay, we came in for a family reunion and originally planning to camp but weren’t able to due to the storm so we found this last min at a decent price point. Staff was very friendly when we came in, seems to be family operated which I like. Room was clean could use some updates but ..."
Reviewed on Sep 27, 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
₩242,717
₩302,486 total
Oct 4 - Oct 5
includes taxes & fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
298 E Haddam Moodus Rd East Haddam CT
₩171,493
₩259,504 total
Oct 1 - Oct 2
includes taxes & fees
9.4/10 Exceptional! (193 reviews)
"Different experiences"
Reviewed on Sep 26, 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.
Frequently asked questions
How much does a Middlesex County vacation package cost?
Create unforgettable memories with our Middlesex County vacation packages, which start from a low . Select the hotels and flights that fit your travel plans. Then, add on one or two tours or activities to cap off your unique escape.
How do I get a cheap travel package to Middlesex County?
Track down flights that suit your busy schedule, add a hotel room to your booking and see how much you save with a Middlesex County vacation package. It's as simple as that! From hotels and flights to rental cars and tours, Expedia makes traveling cheap and easy. And with over 550 partner airlines and 1,000,000 hotel options all over the world to select from, you won't be short of choice.
What are the top hotels in Middlesex County?
When it comes to properties in Old Saybrook, Super 8 by Wyndham Cromwell/Middletown and Pier Blue Inn Old Saybrook - Essex are among the favorites. If you're spending time in Clinton, Quality Inn Cromwell - Middletown and Quality Inn Old Saybrook - Westbrook are waiting to welcome you.
How far in advance should I book my Middlesex County vacation?
It all depends on the air carrier, but you can generally look up international fares on Expedia nearly a year in advance. While it's generally recommended to book ahead of time, lucky travelers occasionally find a cheaper ticket just weeks prior to their intended journey.
What does an Expedia Middlesex County travel package include?
Travel packages include hotels, flights and rental cars, but you can mix and match them to create your perfect Middlesex County vacation. You can also add on fun things like tours and activities once you've made your booking. You're the boss! When you bundle your bookings with Expedia, you'll score discounts you won't find elsewhere.
What should I know before booking a Middlesex County travel package?
Whether it's adventure or relaxation you're craving, a Middlesex County vacation package lets you organize your escape your way. Plus, you'll score great discounts just for combining your hotel with your flights and rental car. The more you bundle, the bigger the savings!
Can I choose my airline with a Middlesex County Expedia vacation package?
Most definitely. Expedia has over 550 airline partners to select from around the globe. With such a big range of choice, finding the right carrier to get you to Middlesex County shouldn't be hard.
If I'm not able to travel, can I cancel my Middlesex County vacation package?
If your vacation plans in Middlesex County have changed, it's a relief to know that it's possible to cancel or amend your booking. If your booking was made in the last 24 hours, you may be able to receive a refund. If your booking is older than that, your hotel, airline or car rental company may impose a fee. For more details, visit our Customer Service Portal.
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.
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.
General Mansfield House
You can spend time studying the exhibits at General Mansfield House during your travels in Middletown. Experience the festivals and entertainment venues in this family-friendly area.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
