Middlesex Vacation Packages
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Your Middlesex Vacation
The adventure-filled city of Middlesex is calling your name. Uncover both its hidden gems and highlights with a Middlesex vacation package that's tailored to you. There's loads to see and do during a trip to Middlesex, including Hanover Museum and Headland. Stop daydreaming and start traveling. Explore the multitude of options on Expedia today and put your Middlesex vacation plans into gear!
Top Middlesex Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Ocho Rios Villa at The Palms
CA $1,808
per person
Nov 30 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Montego Bay (MBJ)
10/10 Exceptional! (2 reviews)
All staff were professional, courteous and friendly. They all went out of their way to grant your requests. The ambience is very nice. The electrical outlets on the patio didn't always work. Had to be creative in getting plugs to stay in. They also need to upgrade from 110v to 220v. Just kidding, but they should have something for travelers from Europe. Internet service was pretty good. Everyone in my group were pleased and would return. The tour setup for us by the manager was fun!!!! Good people, fantastic accommodations. Recommended...
Reviewed on May 8, 2019
Princess Senses The Mangrove Resort - Adults Only
CA $9,504
per person
Dec 4 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Montego Bay (MBJ)
9.4/10 Exceptional! (1,058 reviews)
The rooms are beautiful! I’m in the O’Club. Tons of activities to do. However, the customer service is terrible. The internet has been out 3 of the 4 days I’ve been here, there are rolling blackouts so I wake up hot and sweating in the middle of the night. Everytime I order food at a restaurant, they’re always out of something. I’ve been trying to speak to a manager for the last 3 days and no one is responding. We’re here for a wedding, and they even messed that up. The sound was terrible and they were more concerned with getting out than supporting us. I was thinking about doing my bachelorette trip here, but absolutely not. Please don’t let the looks and the newness fool you, they definitely need to get it together.
Reviewed on Oct 14, 2026
Ready to book your vacation to Middlesex?
Middlesex Hotel Deals
Princess Grand Jamaica Resort - All Inclusive
Industry Cove Green Island Hanover
CA $664
CA $664 total
Oct 28 - Oct 29
includes taxes & fees
Princess Senses The Mangrove Resort - Adults Only
Industry Cove Green Island Hanover
CA $788
CA $788 total
Oct 20 - Oct 21
includes taxes & fees
9.4/10 Exceptional! (1,094 reviews)
"The rooms are beautiful! I’m in the O’Club. Tons of activities to do. However, the customer service is terrible. The internet has been out 3 of the 4 days I’ve been here, there are rolling blackouts so I wake up hot and sweating in the middle of the night. Everytime I order food at a restaurant, ..."
Reviewed on Oct 14, 2026
Deja Resort All Inclusive
92 Gloucester Avenue Montego Bay Saint James
Fully refundableReserve now, pay when you stay
CA $258
CA $305 total
Nov 1 - Nov 2
includes taxes & fees
8.2/10 Very good! (2,004 reviews)
"Nice property,conveniently located, reasonable rate for the amenities they have."
Reviewed on Oct 13, 2026
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 vacation package cost?
You'll find cheap prices from CA $1,808 on Expedia for your Middlesex getaway. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Middlesex costs.
What are the cheapest months to go to Middlesex?
January, February and September are great times to search for cheap Middlesex vacation packages. Travelling in quieter months means you can generally find better prices on flights and accommodations.
How many days is enough for Middlesex?
The ideal length of your Middlesex vacation depends on what you'd like to do and see. Typically, a few days to a week will give you time to go to all the major attractions and explore some hidden gems along the way.
How to find the best Middlesex package deals?
Use Expedia's filters to find some fabulous Middlesex package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Middlesex package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Middlesex vacation as a package?
You can enjoy significant savings on your Middlesex break by booking a personalized vacation package. Check the "Package" heading, then select your travel dates and destination to browse some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Middlesex?
Land incredible discounts by reserving your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Middlesex escape.
How to plan a trip to Middlesex?
- Pick your travel dates: What you'd like to do in Middlesex and your preferred season can help you decide when to get away.
- Calculate your budget: Make sure you have enough money to cover everything from transportation and food to activities and flights. Your hotel will probably be the largest expense during your trip to Middlesex.
- Decide how long to go away for: Now that you're more familiar with Middlesex, you can work out the ideal length of your break. Put together a draft plan and give yourself enough time to cover everything you want to see.
- Combine your accommodations and airfare: Once you've settled on your travel dates and duration, lock in the perfect Middlesex vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
