Middlesex Vacations from $1,215
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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!
The Latest Middlesex vacation packages
Price found within the past 48 hours. Click for updated prices.
Ocho Rios Villa at The Palms
$1,215
per person
Sep 24 - Oct 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
Middlesex Hotel Deals
Princess Grand Jamaica Resort - All Inclusive
Industry Cove Green Island Hanover
$458 nightly
$458 total
Sep 10 - Sep 11
Total with taxes and fees
9/10 Wonderful! (1,581 reviews)
"I had a fairly ok/good time at this resort. The food was okay. I didnt like that they didnt have inclusive things for kids in the late hrs..Kids come with adults and because you have kids doesn't mean your bedtime is 9 or 10 pm too...something like karaoke at 10 should be inclusive. This was over ..."
Reviewed on Aug 11, 2026
Princess Senses The Mangrove Resort - Adults Only
Industry Cove Green Island Hanover
$607 nightly
$607 total
Aug 24 - Aug 25
Total with taxes and fees
9.4/10 Exceptional! (918 reviews)
"Amazing stay very nice property compared to others in Jamaica that we stayed."
Reviewed on Aug 11, 2026
Deja Resort All Inclusive
92 Gloucester Avenue Montego Bay Saint James
$271 nightly
$299 total
Sep 2 - Sep 3
Total with taxes and 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.
Find the Best Middlesex Vacation Packages
Middlesex Essential Information
Language | English |
|---|---|
Currency | Jamaican dollars |
Closest Airport | Sir Donald Sangster Intl. Airport (MBJ) |
Top Sights | Half Moon Beach, Tryall Golf Club and Hanover Museum |
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Frequently asked questions
How much does a Middlesex vacation package cost?
Offering great value package deals from $1,215 on Expedia, you'll be thrilled with how little a vacation to Middlesex costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Middlesex?
If you're looking to snag a cheap Middlesex vacation package, consider planning a trip in April, May and December. You'll typically find better prices on flights and hotels during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Middlesex?
With a well-planned schedule, you can easily visit the main Middlesex sights in a few days. But if you want to discover hidden spots or take day trips, think about booking your Middlesex vacation for longer.
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 escape for midweek, or search for Middlesex package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Middlesex vacation as a package?
You can enjoy significant savings on your Middlesex getaway by booking a customized vacation package. Check the "Package" heading, then enter your travel dates and destination to see the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Middlesex?
If you're planning a spur-of-the-moment Middlesex vacation, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find sensational deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Middlesex vacation packages?
Secure your dream getaway to Middlesex with help from our Book Now, Pay Later vacations. No need to save up or wait for the next payday — we've partnered with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans mean you can spread the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to stay on budget and snap up bargains before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
