Middlesex County Holidays

Photo by Dawn Johnson

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Top destinations in Middlesex County

FlightsFlightsHotelsHotels

Old Saybrook

Old Saybrook

Top Flight + Hotel Deals in Middlesex County

Price found within the past 48 hours. Click for updated prices.
Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Price was €1,969, price is now €1,327 per person
€1,327
per person
2 May - 8 May
found 18 hours ago
Return flight included
Athens (ATH) to New York (JFK)
8.8/10 Excellent! (6,546 reviews)
The best place to stay on a budget if you’re planning to see Broadway shows. I’ve already reserved The St. James for my trip in April.

Reviewed on 6 Feb 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was €2,475, price is now €1,568 per person
€1,568
per person
2 May - 8 May
found 18 hours ago
Return flight included
Athens (ATH) to New York (JFK)
9.2/10 Wonderful! (3,348 reviews)
The staff was nice and the rooms were clean! Great place!

Reviewed on 6 Feb 2026

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was €2,405, price is now €1,594 per person
€1,594
per person
2 May - 8 May
found 18 hours ago
Return flight included
Athens (ATH) to New York (JFK)
9.8/10 Exceptional! (1,411 reviews)
Very clean and great staff! They were very accommodating!

Reviewed on 3 Feb 2026

The Knickerbocker Hotel

The Knickerbocker Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was €2,659, price is now €1,770 per person
€1,770
per person
24 Apr - 3 May
found 15 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (1,664 reviews)
Always love staying at the Knickerbocker. Staff are helpful and kind. Room is very clean and no street noise.

Reviewed on 6 Feb 2026

The Michelangelo Hotel

The Michelangelo Hotel

4 out of 5
Manhattan
Price was €2,385, price is now €1,698 per person
€1,698
per person
20 Apr - 30 Apr
found 12 hours ago
Return flight included
Dublin (DUB) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (1,488 reviews)
Fabulous hotel, great location and very helpful staff.

Reviewed on 6 Feb 2026

Top hotels in Middlesex County

Inn at Middletown

Inn at Middletown

3.5 out of 5
70 Main Street Middletown CT
Fully refundableReserve now, pay when you stay
The price is €176 per night from 8 Mar to 9 Mar
€176
8 Mar - 9 Mar
includes taxes & fees
8.8/10 Excellent! (550 reviews)
The hotel staff and accommodations were great. I would highly recommend it.

Reviewed on 17 Jan 2026

Inn at Middletown
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
7.8/10 Good! (1,001 reviews)
Room was clean and warm and the staff was very friendly

Reviewed on 1 Feb 2026

Get rates
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
Fully refundableReserve now, pay when you stay
The price is €205 per night from 8 Mar to 9 Mar
€205
8 Mar - 9 Mar
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
Great room and staff

Reviewed on 14 Jan 2026

Water's Edge Resort & Spa
See all 3,426 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 €1,327. 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.