Middlesex County Vacation Packages

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Your Middlesex County Vacation

Leave all the planning to us with a Middlesex County vacation package. With everything organized before you leave, the only thing left to do is sit back, relax and experience this destination's countless delights. Begin your trip to Middlesex County with a couple of nights in Old Saybrook visiting popular sights like Westbrook Town Beach and Clinton Crossing Premium Outlets. East Hampton is another city that lures crowds from near and far. TPC River Highlands and Brownstone Exploration & Discovery Park are two of the top places to see here. Expedia is a one-stop shop when it comes to planning your Middlesex County vacation. From accommodations and flights, to car rentals and activities, we're here to help you curate a travel experience like no other.

Top vacation destinations in Middlesex County

Essex showing a house
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Essex

Essex

Top Middlesex County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Benjamin Royal Sonesta New York

The Benjamin Royal Sonesta New York

4.5 out of 5
Manhattan
per person
Sep 17 - Sep 20
found 9 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
8.6/10 Excellent! (1,011 reviews)
Great room , a lot of good places to eat nearby

Reviewed on Aug. 5, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,008 reviews)
Loved everything about it

Reviewed on Aug. 6, 2025

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9/10 Wonderful! (2,737 reviews)
Absolutely amazing hotel, the staff were so friendly and helpful. The breakfast was amazing! I would stay here again!

Reviewed on Aug. 8, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (2,085 reviews)
I enjoyed my short stay at this hotel. It has a modern, boutique feel to it and the staff were friendly and helpful. Our double room was clean and the space was sufficient for 2 people. We did not receive the free bottle of wine that was supposed to come with VIP access.

Reviewed on Aug. 8, 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.8/10 Exceptional! (1,271 reviews)
Amazing stay! Room was spotless and had everything I needed. I even forgot my phone adapter and reception was kind enough to lend me one. I would definitely recommend NobleDEN

Reviewed on Aug. 5, 2025

Middlesex County Hotel Deals

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is CA $483 per night from Aug 26 to Aug 27
CA $483
CA $583 total
Aug 26 - Aug 27
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"Friendly staff, good restaurant"

Reviewed on Aug. 7, 2025

Saybrook Point Resort & Marina
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 CA $110 per night from Aug 17 to Aug 18
CA $110
CA $127 total
Aug 17 - Aug 18
includes taxes & fees
7.6/10 Good! (1,004 reviews)
"Very quiet. Cute little courtyard. Friendly staff."

Reviewed on Aug. 6, 2025

Pier Blue Inn Old Saybrook - Essex
Best Western Mystic Hotel

Best Western Mystic Hotel

2.5 out of 5
48 Whitehall Ave, Mystic, CT
Fully refundableReserve now, pay when you stay
The price is CA $176 per night from Aug 17 to Aug 18
CA $176
CA $202 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (312 reviews)
"Clean, good value. The pool area looked a little rough"

Reviewed on Aug. 6, 2025

Best Western Mystic Hotel
See all 3,301 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.
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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 CA $1,418. 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.