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.
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
Price was CA $1,375, price is now CA $1,128 per person
CA $1,128
per person
Jul 20 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to New Haven (HVN)
8/10 Very Good! (1,612 reviews)
Breakfast was a bit dissapointing but staff were nice and accommodating.

Reviewed on May 29, 2026

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was CA $2,410, price is now CA $1,804 per person
CA $1,804
per person
Jul 20 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to New Haven (HVN)
2/10 (1 review)
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Price was CA $1,534, price is now CA $1,320 per person
CA $1,320
per person
Jul 20 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to New Haven (HVN)
8.6/10 Excellent! (1,306 reviews)
The rooms were nice and big. Kind of weird layout. But my family and I did sleep well in the beds and comfortable pillows. My room had a mini fridge and a small kitchen sink. No microwave. Shower had nice hot water and great water pressure. No carpets in the rooms so it got noisy with people walking around above you. We ate breakfast next door at POPS! And that was DELICIOUS!!!!

Reviewed on May 27, 2026

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
Price was CA $1,488, price is now CA $1,287 per person
CA $1,287
per person
Jul 20 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to New Haven (HVN)
8.8/10 Excellent! (1,062 reviews)
Nice facility. Well situated for Yale Medical facilities, but also walkable to food options closer to Yale’s main campus. It was a hike on foot to Union Station, but easy by car. The room was clean and well designed. The stand-out for me was the fitness facility. Not only was the space large, but the range of equipment was considerably better than average. Extra credit to whoever is responsible for that! If there’s a “but”, although you can make coffee in your room, you will pay for it in the lobby.

Reviewed on May 29, 2026

New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Price was CA $1,719, price is now CA $1,489 per person
CA $1,489
per person
Jul 20 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to New Haven (HVN)
9.2/10 Wonderful! (2,137 reviews)
Love this hotel. I stay in it everytime I go to New Haven. The rooms are great, the staff is friendly and super helpful. It's close to things in the city. Highly recommend.

Reviewed on May 29, 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 $345 per night from Jun 11 to Jun 12
CA $345
CA $420 total
Jun 11 - Jun 12
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
"The location and the amenities provided by the hotel was first classed"

Reviewed on May 27, 2026

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 refundable
The price is CA $121 per night from Jun 7 to Jun 8
CA $121
CA $139 total
Jun 7 - Jun 8
includes taxes & fees
8/10 Very Good! (1,003 reviews)
"We used the place as a crash pad - easy to get to from the marina and close to "the main strip" . We did not have a car and it was a holiday weekend."

Reviewed on May 28, 2026

Pier Blue Inn Old Saybrook - Essex
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 $205 per night from Jun 10 to Jun 11
CA $205
CA $300 total
Jun 10 - Jun 11
includes taxes & fees
9.6/10 Exceptional! (154 reviews)
"Nature path"

Reviewed on May 23, 2026

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
See all 3,479 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 $1,128. 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.