Middlesex Vacations from $617

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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.
Silver Creek Resort

Silver Creek Resort

3.5 out of 5
Price was $2,492, price is now $617 per person
$617
per person
Jun 9 - Jun 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Montego Bay (MBJ)
7/10 Good! (51 reviews)
The only concern we had was that there is no restaurants within walking distance,

Reviewed on May 20, 2024

Hotel Riu Palace Aquarelle - All Inclusive

Hotel Riu Palace Aquarelle - All Inclusive

4 out of 5
Price was $3,286, price is now $1,627 per person
$1,627
per person
May 30 - Jun 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Montego Bay (MBJ)
8.8/10 Excellent! (2,237 reviews)
The internet was slow

Reviewed on Mar 27, 2026

Hotel Riu Montego Bay - Adults Only - All Inclusive

Hotel Riu Montego Bay - Adults Only - All Inclusive

4 out of 5
Price was $3,092, price is now $1,545 per person
$1,545
per person
May 30 - Jun 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Montego Bay (MBJ)
8.6/10 Excellent! (5,183 reviews)
All was good but they don’t have a foot shower when leaving the beach by the beach bar or by building 6 where we entered so people drag a lot of sand in

Reviewed on Mar 27, 2026

Ocho Rios Villa at the Palms V

Ocho Rios Villa at the Palms V

3 out of 5
Save 100% on your flight
Price was $2,665, price is now $1,418 per person
$1,418
per person
May 30 - Jun 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
No reviews
Ocho Rios Villa at the Palms III

Ocho Rios Villa at the Palms III

3.5 out of 5
Price was $2,471, price is now $1,318 per person
$1,318
per person
Jun 10 - Jun 17
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Montego Bay (MBJ)
No reviews
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Middlesex Hotel Deals

Princess Grand Jamaica Resort - All Inclusive

Princess Grand Jamaica Resort - All Inclusive

4.5 out of 5
Industry Cove Green Island Hanover
$496 nightly
The price is $496 total per night from Apr 13 to Apr 14
$496 total
Apr 13 - Apr 14
Total with taxes and fees
8.8/10 Excellent! (764 reviews)
Tons of pools to lounge in for people of all ages, no issues finding a chair either. Beach is just steps from the pools and entertainment going all day long to keep everyone entertained! Staff are very polite and the rooms and facilities are all kept very clean

Reviewed on Mar 26, 2026

Princess Grand Jamaica Resort - All Inclusive
Deja Resort All Inclusive

Deja Resort All Inclusive

3.5 out of 5
92 Gloucester Avenue Montego Bay Saint James
Fully refundableReserve now, pay when you stay
$207 nightly
The price is $228 total per night from Apr 14 to Apr 15
$228 total
Apr 14 - Apr 15
Total with taxes and fees
8/10 Very Good! (1,648 reviews)
Best resort ever! Staff is amazing and the food is great

Reviewed on Mar 27, 2026

Deja Resort All Inclusive
Princess Senses The Mangrove Resort - Adults Only

Princess Senses The Mangrove Resort - Adults Only

4 out of 5
Industry Cove Green Island Hanover
$601 nightly
The price is $601 total per night from Mar 30 to Mar 31
$601 total
Mar 30 - Mar 31
Total with taxes and fees
9.2/10 Wonderful! (557 reviews)
We stayed in a junior suite pleasure room, the O-suites. The room was nice overall and loved the mirror over the bed but did our jacuzzi went out the first 3 nights of our 5 day stay. The food wasn’t great and everything tasted as if it was seasoned the same. $15 up charge for room service and the ...

Reviewed on Mar 26, 2026

Princess Senses The Mangrove Resort - Adults Only
See all 1,530 properties in Middlesex
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 $617 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.