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
FlightsFlightsHotelsHotels

Essex

Essex

Top Middlesex County Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was £1,411, price is now £1,169 per person
£1,169
per person
25 Jul - 1 Aug
found 21 hours ago
Return flight included
London (LON) to New Haven (HVN)
8/10 Very Good! (1,004 reviews)
Parking was easy. Bed mattress terrible. Tired room and furnishings. Basic supplies.

Reviewed on 28 Apr 2026

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
Old Saybrook Center
Price was £2,200, price is now £2,114 per person
£2,114
per person
25 Jul - 1 Aug
found 21 hours ago
Return flight included
London (LON) to New Haven (HVN)
9.6/10 Exceptional! (1,001 reviews)
Everything was super clean and staff was friendly and helpful.

Reviewed on 14 Apr 2026

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 £203 per night from 21 May to 22 May
£203
21 May - 22 May
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
Nice property

Reviewed on 14 May 2026

Water's Edge Resort & Spa
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 £152 per night from 20 May to 21 May
£152
20 May - 21 May
includes taxes & fees
9.6/10 Exceptional! (150 reviews)
Postcards really thought of everything you could want or need for a short stay in the woods. It was exactly what we needed!

Reviewed on 11 May 2026

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
The price is £108 per night from 7 Jun to 8 Jun
£108
7 Jun - 8 Jun
includes taxes & fees
9.2/10 Wonderful! (2,120 reviews)
We weren’t happy that parking was $24 a day and that the only part of the breakfast that was free was the coffee. Otherwise, everything else was fine.

Reviewed on 12 May 2026

New Haven Hotel
See all 3,493 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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All Inclusive Holidays
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Family Friendly Holidays

Frequently asked questions

How much does a Middlesex County travel package cost?
Our Middlesex County packages, which start at just £1,169, 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.