Middlesex County Holidays

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Your Middlesex County Holiday

Leave all the planning to us with a Middlesex County holiday package. With everything organised 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 holiday. From accommodation 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

A sandy beach with a breakwater, calm sea, and a clear sky.
FlightsFlightsHotelsHotels

Westbrook

Westbrook

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

Our pick of the best Middlesex County Hotel Deals

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundable
The price is AU$142 per night from 12 July to 13 July
AU$142
12 July - 13 July
includes taxes & fees
8/10 Very good! (1,011 reviews)
"Ithe bathroom could be updated."

Reviewed on 8 July 2026

Pier Blue Inn Old Saybrook - Essex
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is AU$603 per night from 22 July to 23 July
AU$603
22 July - 23 July
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"Our room was lovely however it was on the second floor of the building with no elevator. There were 14 steep steps that had to be climbed. My husband (84) had trouble doing this. We were not notified of the steps when we made our reservations. When I asked for a different room, I was told they were ..."

Reviewed on 10 July 2026

Water's Edge Resort & Spa
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

2.5 out of 5
298 E Haddam Moodus Rd East Haddam CT
The price is AU$318 per night from 9 Aug to 10 Aug
AU$318
9 Aug - 10 Aug
includes taxes & fees
9.6/10 Exceptional! (163 reviews)
"Amazing woodland views and privacy. My wife didn’t want to leave. Great place to leave the world behind and just relax."

Reviewed on 6 July 2026

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
See all 3,481 properties in Middlesex County
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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beach holidays
Beach Holidays
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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

A steam locomotive with the number 40 on its front, traveling on a railway track.
Photo by Bill Dillard
Open 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.
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What to do in Middlesex County

Connecticut Coloured Regiment Parade Route: An Audio Tour

Connecticut Coloured Regiment Parade Route: An Audio Tour

AU$14
per adult
Connecticut Coloured Regiment Parade Route: An Audio Tour
See all activities in Middlesex County
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.