Middlesex County Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
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 Middlesex County Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
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
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
£72
10 Sept - 11 Sept
includes taxes & fees
8/10 Very good! (1,015 reviews)
"Welcoming, helpful, friendly, professional front desk staff. My room was impeccably clean and tidy. The property is centrally-located with ease of accessibility to main roads and major highways, yet far enough off Boston Post Road to ensure a quiet, peaceful and restful stay. Overall, an outstanding, ..."
Reviewed on 8 Sept 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
£165
7 Oct - 8 Oct
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
"Excellent staff and location. The food was mediocre"
Reviewed on 7 Sept 2026
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
298 E Haddam Moodus Rd East Haddam CT
£186
7 Oct - 8 Oct
includes taxes & fees
9.4/10 Exceptional! (187 reviews)
"The staff was great addressed a small issue quickly. The cabin was clean and ready for us, this was a first for me I have never been camping of any kind. What I enjoyed most was the quiet and being away from the everyday hustle, myself and my wife enjoyed the slowdown along with our dog, just being ..."
Reviewed on 7 Sept 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 travel package cost?
Our Middlesex County packages, which start at just £696, 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.
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.
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)
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?
General Mansfield House
You can spend time browsing the exhibits at General Mansfield House during your trip to Middletown. Experience the festivals and entertainment venues in this family-friendly area.
What to do in Middlesex County
Connecticut Coloured Regiment Parade Route: An Audio Tour
£7
per adult
* 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.
