Middlesex County Packages (Flight + Hotel)

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Top hotels in Middlesex County

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
The price is ฿3,005 per night from 14 Jul to 15 Jul
฿3,005
฿3,456 total
14 Jul - 15 Jul
includes taxes & fees
8/10 Very good! (1,009 reviews)
"Lage room, Clean and comfortable bed. Bathroom could use updating and an elevated toilet seat. Staff very nice. Would stay again."

Reviewed on 7 Jul 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
The price is ฿11,642 per night from 22 Jul to 23 Jul
฿11,642
฿13,964 total
22 Jul - 23 Jul
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"Beautiful property. Sunday Brunch was excellent. Staff is friendly."

Reviewed on 1 Jul 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 ฿5,624 per night from 20 Jul to 21 Jul
฿5,624
฿7,998 total
20 Jul - 21 Jul
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 Jul 2026

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
See all 3,474 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.

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.
See properties

What to do in Middlesex County

Connecticut Coloured Regiment Parade Route: An Audio Tour

Connecticut Coloured Regiment Parade Route: An Audio Tour

฿328
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.