Middlesex County Holidays

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Top destinations in Middlesex County

A rocky beach with large boulders and the ocean in the background.
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Old Saybrook

Old Saybrook

Our pick of the best Middlesex County Hotel Deals

Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is NZ$694 per night from 21 July to 22 July
NZ$694
21 July - 22 July
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"we stayed for weekend had a great time beautiful room comfortable bed amazing spa tub restraunt food and bar convenient & delicious staff very nice"

Reviewed on 25 June 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 NZ$182 per night from 7 July to 8 July
NZ$182
7 July - 8 July
includes taxes & fees
8/10 Very good! (1,002 reviews)
"staff and parking"

Reviewed on 22 June 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 NZ$375 per night from 29 July to 30 July
NZ$375
29 July - 30 July
includes taxes & fees
9.6/10 Exceptional! (160 reviews)
"I stayed here, but there was no lantern or scissors provided, and the lantern in my friend’s unit was broken too. So I asked for a replacement, but I was told there wasn’t one available and to just deal with it. I asked them to help resolve the issue, but all they said was to talk to the manager ..."

Reviewed on 26 June 2026

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
See all 3,475 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 suspension bridge over a body of water, a large white building with a tower, and a forested hill in the background.

Goodspeed Opera House

9.0/5 (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.
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What to do in Middlesex County

Connecticut Coloured Regiment Parade Route: An Audio Tour

Connecticut Coloured Regiment Parade Route: An Audio Tour

NZ$17
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.