Middlesex County Vacations & Trips from ￥298,968

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Top destinations in Middlesex County

Arrigoni Bridge
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Cromwell

Cromwell

The Latest Middlesex County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Candlewood Suites New York City-Times Square by IHG

Candlewood Suites New York City-Times Square by IHG

2.5 out of 5
Manhattan
Price was ￥415,525, price is now ￥298,968 per person
￥298,968
per person
May 22 - May 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (1,755 reviews)
Not bad acces to Times Square but old building and smelled like smoke in the room.

Reviewed on Mar 11, 2026

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was ￥1,227,177, price is now ￥780,592 per person
￥780,592
per person
May 22 - May 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,001 reviews)
Excellent stay, very clean spacious rooms. Location is great - close to everything. Only downfall was the bathroom, very tiny with a pedestal sink right next to the toilet, not great for women who need to get ready.

Reviewed on Feb 24, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was ￥521,913, price is now ￥340,464 per person
￥340,464
per person
May 22 - May 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,419 reviews)
Excellent location & staff very helpful. Only drawback was elevators. Early mornings there was only 1 operating in mornings from 6-10:00am. They used other 2 to transport people to 5th floor.(restaurant location.). Had to walk down 12 flights to make my breakfast reservation. Couldn’t get on the one elevator that was available.

Reviewed on Mar 9, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was ￥683,072, price is now ￥445,864 per person
￥445,864
per person
Apr 28 - May 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (2,923 reviews)
Great location, clean, courteous staff, breakfast buffet had lots of options. Would definately stay again.

Reviewed on Mar 5, 2026

Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Price was ￥533,140, price is now ￥377,346 per person
￥377,346
per person
Apr 28 - May 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (7,024 reviews)
La ubicación se me hizo adecuada ya que es céntrica, está cerca el times square, y a dos cuadras el metro. Hay tiendas de 24 horas muy cerca. La habitación la entregaron limpia y también hacían el aseo cuando lo solicitábamos, agua caliente, el staff muy amables y atentos. Solo el wifi a veces era lento más en la noches supongo porque ya todos llegábamos a esa hora :)

Reviewed on Mar 10, 2026

Middlesex County Hotel Deals

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 ￥31,315 per night from Apr 7 to Apr 8
￥31,315
￥39,175 total
Apr 7 - Apr 8
includes taxes & fees
9/10 Wonderful! (555 reviews)
Clean room

Reviewed on Feb 24, 2026

Inn at Middletown
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 ￥26,729 per night from Apr 1 to Apr 2
￥26,729
￥33,466 total
Apr 1 - Apr 2
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
This was my first time at Water’s Edge and will definitely not be my last. Our stay was wonderful. Becky at the front desk was

Reviewed on Mar 7, 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 ￥14,653 per night from Mar 16 to Mar 17
￥14,653
￥24,126 total
Mar 16 - Mar 17
includes taxes & fees
9.6/10 Exceptional! (121 reviews)
Staff was very courteous helpful and responsive. The outdoor space was nice and the bed was very comfortable. Very cool experience!!

Reviewed on Feb 28, 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 vacation package cost?
Create unforgettable memories with our Middlesex County vacation packages, which start from a low ￥298,968. 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 vacation package. It's as simple as that! From hotels and flights to rental cars and tours, Expedia makes traveling 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 favorites. 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 vacation?
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 travelers 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 vacation. 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 vacation package lets you organize 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 vacation 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 vacation package?
If your vacation 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.