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

Arrigoni Bridge
FlightsFlightsHotelsHotels

Cromwell

Cromwell
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Essex

Essex

Top Middlesex County Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was £5,782, price is now £4,936 per person
£4,936
per person
27 Aug - 2 Sept
found 1 hour ago
Return flight included
London (LHR) to New Haven (HVN)
No reviews

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

Top hotels in Middlesex County

Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
The price is £234 per night from 15 Jun to 16 Jun
£234
15 Jun - 16 Jun
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"The location and the amenities provided by the hotel was first classed"

Reviewed on 27 May 2026

Water's Edge Resort & Spa
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 £84 per night from 11 Jun to 12 Jun
£84
11 Jun - 12 Jun
includes taxes & fees
8/10 Very Good! (1,001 reviews)
"Like most of the hotels in Ct. Old, but this clean and well maintained. I recommend it if you travel to This Ct shore area"

Reviewed on 6 Jun 2026

Pier Blue Inn Old Saybrook - Essex
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

2 out of 5
298 E Haddam Moodus Rd East Haddam CT
The price is £172 per night from 16 Jun to 17 Jun
£172
16 Jun - 17 Jun
includes taxes & fees
9.6/10 Exceptional! (156 reviews)
"Def not up to the Marriott Bonvoy brand. These aren’t cabins - they’re tiny homes/mobile homes. They are super small. Mine didn’t have AC and it was a hot muggy weekend. In town for a funeral and the room has no hair dryer, no mirror - at all nevermind a full length, no closet and no bathroom sink, ..."

Reviewed on 8 Jun 2026

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
See all 3,487 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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Frequently asked questions

How much does a Middlesex County travel package cost?
Our Middlesex County packages, which start at just £4,936, are the perfect way to save loads of cash. Select your preferred flights, hotels and rental cars to create a personalized escape.
If I'm not able to travel, can I cancel my Middlesex County travel package?
Your situation can change suddenly, so yes, you can. You may be able to change or cancel your Middlesex County travel package at no cost within 24 hours of booking. For bookings older than that, you can still cancel or make changes, but your hotel, car rental company or airline may charge a fee. Want more information? Visit our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.
How do I get a cheap travel package to Middlesex County?
Combine your flights and hotels, add on extras such as tours, and save with a Middlesex County holiday package. You won't just land wonderful discounts on your escape — you'll have lots of choice at your fingertips too. When you book with Expedia, you can choose from more than 550 air carriers and 1,000,000 properties globally. Your next affordable adventure starts right here, right now!
Does Expedia offer Book Now, Pay Later Middlesex County holidays?
Yes, we do. Expedia has partnered with online lender Klarna to help you conveniently pay for your holiday in instalments. Simply choose the payment plan that suits you best during checkout and take away the stress of budgeting for your trip. Don't forget to bundle your flights, hotel and car hire with Expedia to get the biggest bang for your buck. Browse our flexible payment options below:

  • Pay monthly holidays: If paying small amounts each month works for you, Klarna can help. Paying in convenient monthly instalments will make your holiday dreams come true.
  • Pay in instalments holidays: Into the idea of paying off your holiday in multiple transactions? Consider this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: When you stumble on an unbeatable deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you lock in your getaway.

What are the top hotels in Middlesex County?
Look up Saybrook Point Resort & Marina and Pier Blue Inn Old Saybrook - Essex. They're the first choice for many travellers headed to Old Saybrook. If Clinton is next stop on your itinerary, Saybrook Point Resort & Marina and Pier Blue Inn Old Saybrook - Essex are two cosy options.
How far in advance should I book my Middlesex County holiday?
It all depends on the air carrier, but you can normally browse through international flights on Expedia up to 12 months in advance. While it's a good idea to book ahead of time, lucky travellers occasionally score a cheaper ticket only weeks before their intended journey.
What does an Expedia Middlesex County travel package include?
You can select from any combination of hotels, flights and rental cars. Once you've made your booking, you can add the fun stuff like tours and activities. Want to pick your airfare class? That's easy to do too. The choice is all yours when it comes to crafting your perfect Middlesex County trip.
What should I know before booking a Middlesex County travel package?
You can save big by bundling your hotels, airfares and rental cars. Once you've made your booking, you can add on tours and activities. Your next awesome adventure is only a few clicks away.
Can I choose my airline with a Middlesex County Expedia travel package?
With a travel package, you're always in charge. Whether you'd like to fly to Middlesex County in coach or first class, simply choose from the available airline options. Expedia has access to more than 550 partner airlines across the world.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.