Middlesex Vacations from $900

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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.
Alamanda Cottage at Serenity

Alamanda Cottage at Serenity

3 out of 5
Ironshore
Price was $2,216, price is now $900 per person
$900
per person
Jan 9 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
No reviews
Sunset at the Palms Resort - Adults Only - All Inclusive

Sunset at the Palms Resort - Adults Only - All Inclusive

4.5 out of 5
Price was $5,743, price is now $1,932 per person
$1,932
per person
Jan 22 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
9/10 Wonderful! (1,002 reviews)
Staff was extremely friendly. The beach was awesome, calm water clear, palm trees. Was truly remarkable, will be back for one year anniversary.

Reviewed on Nov 3, 2025

The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive

The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive

5 out of 5
Price was $14,291, price is now $6,434 per person
$6,434
per person
Jan 11 - Jan 16
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Montego Bay (MBJ)
10/10 Exceptional! (2 reviews)
Excellent Resort, especially all the excellence club amenities

Reviewed on May 1, 2025

Ocean Coral Spring - All Inclusive

Ocean Coral Spring - All Inclusive

5 out of 5
Price was $2,424, price is now $1,104 per person
$1,104
per person
Jan 9 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
8.4/10 Very Good! (3,912 reviews)
Poor customer service. Wanted guest to pay fees while in the bad hurricane storm.. treated the guest bad along taking the WiFi from the resort..

Reviewed on Nov 1, 2025

Ocho Rios Villa at The Palms

Ocho Rios Villa at The Palms

3 out of 5
Price was $2,467, price is now $1,145 per person
$1,145
per person
Jan 25 - Jan 31
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
10/10 Exceptional! (2 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
$450 nightly
The price is $450 total per night from Dec 1 to Dec 2
$450 total
Dec 1 - Dec 2
Total with taxes and fees
8.8/10 Excellent! (699 reviews)
We were there the weekend before the hurricane hit Jamaica. The resort was amazing, the staff was amazing, the butlers Richardo and Thorniel were amazing, the life guards at the water park treated us like family. The bartenders were top notch and made great drinks. Shoutout to O’Shea. The food was ...

Reviewed on Nov 7, 2025

Princess Grand Jamaica 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
$511 nightly
The price is $511 total per night from Dec 1 to Dec 2
$511 total
Dec 1 - Dec 2
Total with taxes and fees
9/10 Wonderful! (420 reviews)
Excellent staff

Reviewed on Nov 7, 2025

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

Deja Resort All Inclusive

3.5 out of 5
92 Gloucester Avenue, Montego Bay, Saint James
$189 nightly
The price is $209 total per night from Dec 1 to Dec 2
$209 total
Dec 1 - Dec 2
Total with taxes and fees
8/10 Very Good! (1,458 reviews)
Excellent service and clean rooms

Reviewed on Nov 2, 2025

Deja Resort All Inclusive
See all 1,485 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 $900 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.