Middlesex County Holidays

Photo by Dawn Johnson

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Middlesex County Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Manhattan
Price was S$1,036, price is now S$714 per person
S$714
per person
13 Feb - 16 Feb
found 17 hours ago
Return direct flight included
Dallas (DFW) to New York (JFK)
7.4/10 Good! (5,413 reviews)
Everyday we felt well taken care of and the first priority of each staff member we encountered. I can’t believe how many negative reviews I read that had to be false. Not a single elevator issue, staff member issue, room was great, bed was comfortable, room was attended to each day, and the staff even tucked in my daughter and her friends build a bear each day while attending to the room.

Reviewed on 9 Jan, 2026

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Save 100% on your flight
Price was S$1,651, price is now S$823 per person
S$823
per person
13 Feb - 16 Feb
found 17 hours ago
Return direct flight included
Dallas (DFW) to New York (JFK)
9.2/10 Wonderful! (2,008 reviews)
The hospitality and customer service is top tier. The ambiance is modern, clean, and the city view was incredible of the Empire State Building.Our family loves staying at the various Melia hotels.

Reviewed on 8 Jan, 2026

Fouquet's New York

Fouquet's New York

5 out of 5
Manhattan
Save 100% on your flight
Price was S$3,154, price is now S$1,869 per person
S$1,869
per person
13 Feb - 16 Feb
found 17 hours ago
Return direct flight included
Dallas (DFW) to New York (JFK)
9.6/10 Exceptional! (60 reviews)
Lovely staff. Incredible property. The hype is real. This is by far and away the nicest property we’ve stayed at in Manhattan in a long time.

Reviewed on 10 Oct, 2025

OYO Times Square

OYO Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was S$1,132, price is now S$734 per person
S$734
per person
13 Feb - 16 Feb
found 17 hours ago
Return direct flight included
Dallas (DFW) to New York (JFK)
7.2/10 Good! (1,617 reviews)
Maria was amazing. She made our stay perfect. Unfortunately Breakfast was not explained to us and we were not aware it was offered.

Reviewed on 10 Jan, 2026

The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Manhattan
Price was S$1,057, price is now S$721 per person
S$721
per person
13 Feb - 16 Feb
found 17 hours ago
Return direct flight included
Dallas (DFW) to New York (JFK)
9/10 Wonderful! (1,825 reviews)
I was impressed with the size of our apartment and enjoyed that the bedroom had a door separating it from the living room, so our kids who were sleeping on the foldout sofa bed could watch tv in the morning while we slept in a little. The midtown location was very convenient. The room was mostly clean, though there was a used tissue on the floor under the sofa bed when I pulled it out.

Reviewed on 6 Jan, 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 S$256 per night from 8 Feb to 9 Feb
S$256
8 Feb - 9 Feb
includes taxes & fees
8.8/10 Excellent! (548 reviews)
Staff was wonderful, lovely hotel

Reviewed on 5 Jan, 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 S$361 per night from 11 Jan to 12 Jan
S$361
11 Jan - 12 Jan
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
Great place!

Reviewed on 31 Dec, 2025

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 refundableReserve now, pay when you stay
7.8/10 Good! (1,001 reviews)
muy limpias

Reviewed on 8 Jan, 2026

Get rates
Pier Blue Inn Old Saybrook - Essex
See all 3,422 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 S$714. 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.