Middlesex County Holidays
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Top destinations in Middlesex County
Our pick of the best Middlesex County Hotel Deals
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
NZ$200
27 Aug - 28 Aug
includes taxes & fees
8/10 Very good! (1,000 reviews)
"It was a very nice hotel. The room was clean and comfortable, the staff was friendly, and the location was convenient. We had a great stay and really enjoyed our time there."
Reviewed on 11 Aug 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
NZ$521
31 Aug - 1 Sept
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
"This is one of our most favorites! The rooms are amazing ( we prefer to spend a little extra for the ocean view). Dinner there is great!. The staff is exceptional."
Reviewed on 11 Aug 2026
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
298 E Haddam Moodus Rd East Haddam CT
NZ$420
10 Sept - 11 Sept
includes taxes & 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 9 Aug 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 holiday package cost?
Create unforgettable memories with our Middlesex County holiday 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 holiday package. It's as simple as that! From hotels and flights to rental cars and tours, Expedia makes travelling 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 favourites. 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 holiday?
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 travellers 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 holiday. 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 holiday package lets you organise 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 holiday 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 holiday package?
If your holiday 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 exploring the galleries in 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 on your trip to East Haddam. Wander the riverfront and beaches in the area.
Harvey's Beach
8.8/10 (93 reviews)
If a restful holiday is part of your travel plans, Harvey's Beach might be the perfect place to visit 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)
Take a campus tour or just explore the area of 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 do some window-shopping at Clinton Crossing Premium Outlets during your trip to 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 savour the top-notch restaurants.
What to do in Middlesex County
Connecticut Coloured Regiment Parade Route: An Audio Tour
NZ$17
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
