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

FlightsFlightsHotelsHotels

Essex

Essex

Top Middlesex County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Arthouse Hotel New York City

Arthouse Hotel New York City

4 out of 5
Manhattan
Price was CA $1,845, price is now CA $1,147 per person
CA $1,147
per person
Jun 3 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (1,852 reviews)
Complementary pastry amazing. Staff was absolutely fantastic…professional and nice.

Reviewed on Apr 9, 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was CA $3,562, price is now CA $2,145 per person
CA $2,145
per person
Jun 3 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,003 reviews)
Everything is great about this Hotel.

Reviewed on Apr 9, 2026

Park Lane New York

Park Lane New York

5 out of 5
Manhattan
Price was CA $2,449, price is now CA $1,501 per person
CA $1,501
per person
Jun 3 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,764 reviews)
Great location; Central Park View is a must

Reviewed on Apr 11, 2026

The William Vale

The William Vale

5 out of 5
Price was CA $2,449, price is now CA $1,503 per person
CA $1,503
per person
May 27 - May 31
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,026 reviews)
Great calm and well Located place to stay. Amazing view and dinning options.

Reviewed on Apr 3, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $3,274, price is now CA $2,052 per person
CA $2,052
per person
May 15 - May 18
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,003 reviews)
Decent enough ‘trendy’ hotel, pool is dumb (“no swimming”?!), w the entire place seemingly catering to younger people w bad taste. The rooftop is loud and obnoxious, but if that’s your thing, have at it. Location is great, staff just ok on average, style over substance though, ultimately :/

Reviewed on Apr 9, 2026

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 CA $329 per night from Apr 19 to Apr 20
CA $329
CA $403 total
Apr 19 - Apr 20
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
it was our first time and we really enjoyed the place. The Band was amazing! Being at the resort made our weekend great. Will definitely be back!

Reviewed on Apr 11, 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 CA $152 per night from Apr 21 to Apr 22
CA $152
CA $238 total
Apr 21 - Apr 22
includes taxes & fees
9.6/10 Exceptional! (134 reviews)
The check-in process was very easy. The passcode to get into the cabin was provided about two hours before check-in. Upon arrival, the cabin was very clean and stocked with necessities. I was able to keep in contact with the staff via text and they were very prompt to respond.

Reviewed on Apr 10, 2026

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Fully refundable
The price is CA $168 per night from May 3 to May 4
CA $168
CA $194 total
May 3 - May 4
includes taxes & fees
9.2/10 Wonderful! (2,086 reviews)
Hotel is in a great location, perfect for walking around the area. Nearby parking is very convenient, but tight. Staff was friendlt, everything was clean, room was large and quality was fantastic. Would stay here again.

Reviewed on Apr 12, 2026

New Haven Hotel
See all 3,518 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.
All Inclusive Vacations
All Inclusive Vacations
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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 $1,147. 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.