
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.


Sunset at the Palms Resort - Adults Only - All Inclusive
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
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
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

Middlesex Hotel Deals

Princess Grand Jamaica Resort - All Inclusive
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 Senses The Mangrove Resort - Adults Only
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

Deja Resort All Inclusive
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
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















