Middlesex County Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top destinations in Middlesex County

Beautiful sunrise at the mouth of the Connecticut River, Old Saybrook, Connecticut.
FlightsFlightsHotelsHotels

Old Saybrook

Old Saybrook
Arrigoni Bridge
FlightsFlightsHotelsHotels

Cromwell

Cromwell

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 20 May to 21 May
€234
20 May - 21 May
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
Great views from the restaurant and bar area. Staff were very friendly and attentive. Will stay here again.

Reviewed on 8 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 €175 per night from 10 Jun to 11 Jun
€175
10 Jun - 11 Jun
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 €124 per night from 7 Jun to 8 Jun
€124
7 Jun - 8 Jun
includes taxes & fees
9.2/10 Wonderful! (2,144 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.

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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.