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

A quaint white building with a dark shingled roof, a flag, and a sign reading "Toys Ahoy".
FlightsFlightsHotelsHotels

Essex

Essex

Top Middlesex County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Liberty Inn

Liberty Inn

2 out of 5
Price was CA $792, price is now CA $763 per person
CA $763
per person
Aug 27 - Aug 31
found 23 hours ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
7.6/10 Good! (657 reviews)
I stayed here with my girlfriend over the July fourth weekend. It was inexpensive. Enjoyable. And the staff was super friendly. The television hadthebtelemundk channel which was awesome because it aired the word cup soccer games. The staff was excellent. Front desk help was superb.

Reviewed on Jul 10, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was CA $4,279, price is now CA $3,302 per person
CA $3,302
per person
Aug 22 - Aug 29
found 3 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to New Haven (HVN)
No reviews

Quality Suites Stratford

Quality Suites Stratford

2.5 out of 5
Price was CA $1,086, price is now CA $1,042 per person
CA $1,042
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to New Haven (HVN)
8.2/10 Very good! (1,004 reviews)
Front desk was always staffed and helpful, even at 6 am, I was able to check in early without asking ahead of time, and with no problem. Very happy with the room, very clean.

Reviewed on Jul 14, 2026

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was CA $1,027, price is now CA $910 per person
CA $910
per person
Aug 27 - Aug 31
found 23 hours ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8/10 Very good! (1,001 reviews)
Still the same wonderful little place as the last time I stayed here!

Reviewed on Jul 11, 2026

Middlesex County Hotel Deals

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 $129 per night from Jul 20 to Jul 21
CA $129
CA $148 total
Jul 20 - Jul 21
includes taxes & fees
8/10 Very good! (1,000 reviews)
"Still the same wonderful little place as the last time I stayed here!"

Reviewed on Jul 11, 2026

Pier Blue Inn Old Saybrook - Essex
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
The price is CA $420 per night from Aug 12 to Aug 13
CA $420
CA $508 total
Aug 12 - Aug 13
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
"Hopefully next time the room will be better and the cappuccino machine at Starbucks and the slushy machine at the pool are workin. Grounds are absolutely breathtaking"

Reviewed on Jul 13, 2026

Water's Edge Resort & Spa
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

2.5 out of 5
298 E Haddam Moodus Rd East Haddam CT
The price is CA $190 per night from Jul 28 to Jul 29
CA $190
CA $283 total
Jul 28 - Jul 29
includes taxes & fees
9.6/10 Exceptional! (164 reviews)
"Peaceful setting"

Reviewed on Jul 14, 2026

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
See all 3,487 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 $763. 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.

Stay near popular Middlesex County attractions

A steam locomotive with the number 40 on its front, traveling on a railway track.
Photo by Bill Dillard
Open Photo by Bill Dillard

Essex Steam Train

8.4/10 (165 reviews)
You can spend time browsing the exhibits at Essex Steam Train during your travels in Essex Village. While you're in the area, stroll along the beautiful beaches.
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What to do in Middlesex County

Connecticut Coloured Regiment Parade Route: An Audio Tour

Connecticut Coloured Regiment Parade Route: An Audio Tour

CA $14
per adult
Connecticut Coloured Regiment Parade Route: An Audio Tour
See all activities in Middlesex County
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.