Middlesex Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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 $1,771
per person
Nov 14 - Nov 20
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
Ocean Coral Spring - All Inclusive
CA $4,234
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Montego Bay (MBJ)
8.4/10 Very good! (4,288 reviews)
Lots of activities.. The rooms are spacious..We had a swim up pool that we loved.. The toilets are too low especially for the elderly or bad knees .The food choices were limited in the buffet.Favorite restaurant was Red Snapper.
The staff was ok not exceptional.
Reviewed on Oct 14, 2026
Sunset at the Palms Resort - Adults Only - All Inclusive
CA $3,383
per person
Nov 14 - Nov 21
found 15 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Montego Bay (MBJ)
9.2/10 Wonderful! (1,003 reviews)
The workers at this resort will make sure your stay is perfect, beautiful place all around.
Reviewed on Oct 11, 2026
Princess Senses The Mangrove Resort - Adults Only
CA $3,657
per person
Nov 14 - Nov 21
found 15 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Montego Bay (MBJ)
9.4/10 Exceptional! (1,058 reviews)
Everything was amazing excellent customer service and staff and butler
Reviewed on Oct 15, 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 26 - Oct 27
includes taxes & fees
Princess Senses The Mangrove Resort - Adults Only
Industry Cove Green Island Hanover
CA $788
CA $788 total
Oct 25 - Oct 26
includes taxes & fees
9.4/10 Exceptional! (1,097 reviews)
"Everything was amazing excellent customer service and staff and butler"
Reviewed on Oct 15, 2026
Deja Resort All Inclusive
92 Gloucester Avenue Montego Bay Saint James
Fully refundableReserve now, pay when you stay
CA $268
CA $316 total
Oct 19 - Oct 20
includes taxes & fees
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 $1,771 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.
