Middlesex County Vacation Packages
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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 vacation destinations in Middlesex County
Essex
Top Middlesex County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Middlesex County Hotel Deals
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundable
CA $120
CA $138 total
Aug 23 - Aug 24
includes taxes & fees
8/10 Very good! (1,013 reviews)
"Clean room with crisp cold A/C. If you’re in the area and need a place to stay I would definitely recommend Pier Blue Inn. Helpful friendly staff."
Reviewed on Aug 22, 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
CA $321
CA $393 total
Sep 15 - Sep 16
includes taxes & fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
298 E Haddam Moodus Rd East Haddam CT
CA $186
CA $340 total
Sep 21 - Sep 22
includes taxes & fees
9.4/10 Exceptional! (181 reviews)
"Our second time at post card cabins and we really enjoy it. Our only complaint this time around is that we texted saying we didn’t need anything replenished and then someone showed up midday and loudly knocked on our cabin (after we had just fallen asleep for a nap) so that was unfortunate. Also ..."
Reviewed on Aug 17, 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 CA $1,328. 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.
Photo by Dawn Johnson
Machimoodus State Park
You can take time to visit Machimoodus State Park during your travels to Moodus. Amble around this family-friendly area's riverfront or experience its entertainment venues.
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.
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.
Westbrook Town Beach
8.8/10 (36 reviews)
Why not spend a lazy afternoon at Westbrook Town Beach during your trip to Westbrook?
What to do in Middlesex County
Connecticut Coloured Regiment Parade Route: An Audio Tour
CA $14
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
