Middlesex Vacations from $737

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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.
Blue Seas Two Unity Hall

Blue Seas Two Unity Hall

3 out of 5
Price was $1,621, price is now $737 per person
$737
per person
Jan 23 - Jan 26
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Montego Bay (MBJ)
No reviews

Ocho Rios Villa at The Palms

Ocho Rios Villa at The Palms

3 out of 5
Price was $2,781, price is now $1,347 per person
$1,347
per person
Dec 29 - Jan 5
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

Hotel Riu Montego Bay - Adults Only - All Inclusive

Hotel Riu Montego Bay - Adults Only - All Inclusive

4 out of 5
Price was $3,554, price is now $1,771 per person
$1,771
per person
Jan 14 - Jan 19
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Montego Bay (MBJ)
8.6/10 Excellent! (5,633 reviews)
Great staff great vibes

Reviewed on Nov 13, 2026

Hotel Riu Palace Aquarelle - All Inclusive

Hotel Riu Palace Aquarelle - All Inclusive

4 out of 5
Falmouth Historic Town Centre
Price was $3,459, price is now $1,734 per person
$1,734
per person
Jan 14 - Jan 19
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Montego Bay (MBJ)
8.8/10 Excellent! (3,192 reviews)

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

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

5 out of 5
Price was $6,067, price is now $3,044 per person
$3,044
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Montego Bay (MBJ)
9.4/10 Exceptional! (1,105 reviews)

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Middlesex Hotel Deals

Princess Grand Jamaica Resort - All Inclusive

Princess Grand Jamaica Resort - All Inclusive

5 out of 5
Industry Cove Green Island Hanover
$519 nightly
The price is $519 total per night from Nov 19 to Nov 20
$519 total
Nov 19 - Nov 20
Total with taxes and fees
9/10 Wonderful! (1,970 reviews)
"Wonderful stay with the family. The kids loved going to the kids club. Tons of options for food."

Reviewed on Nov 13, 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
$202 nightly
The price is $226 total per night from Nov 23 to Nov 24
$226 total
Nov 23 - Nov 24
Total with taxes and fees
8.2/10 Very Good! (2,020 reviews)
"For a small all inclusive hotel, I was very pleased with the services. The food was clean and of a very good quality, choices and was tasty. The staff were excellent. Being an older facility, few fixtures etc could be upgraded but the place was clean and comfortable. You cannot beat the central location. ..."

Reviewed on Nov 12, 2026

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

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

5 out of 5
Industry Cove Green Island Hanover
$616 nightly
The price is $616 total per night from Nov 15 to Nov 16
$616 total
Nov 15 - Nov 16
Total with taxes and fees
Princess Senses The Mangrove Resort - Luxury Adults Only - All Inclusive
See all 1,576 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 $737 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.