Middlesex Vacations from $704

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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 $2,950, price is now $704 per person
$704
per person
Jul 13 - Jul 19
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

Ocho Rios Villa at The Palms

Ocho Rios Villa at The Palms

3 out of 5
Price was $2,602, price is now $1,200 per person
$1,200
per person
Jul 13 - Jul 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Montego Bay (MBJ)
10/10 Exceptional! (2 reviews)
Hotel Riu Palace Aquarelle - All Inclusive

Hotel Riu Palace Aquarelle - All Inclusive

4 out of 5
Falmouth Historic Town Centre
Price was $3,687, price is now $1,714 per person
$1,714
per person
Jul 13 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Montego Bay (MBJ)
8.8/10 Excellent! (2,480 reviews)
This is a nice property and we enjoyed our stay. We will definitely recommend. The food was great.

Reviewed on May 12, 2026

Excellence Oyster Bay - Adults Only All Inclusive

Excellence Oyster Bay - Adults Only All Inclusive

5 out of 5
Price was $5,123, price is now $2,414 per person
$2,414
per person
Jun 29 - Jul 6
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Montego Bay (MBJ)
9.2/10 Wonderful! (1,263 reviews)
This place exceeded our expectations. Every staff member was so friendly and the resort is so beautiful. It was the perfect place to relax and celebrate our anniversary. Also, all the food was amazing!

Reviewed on May 11, 2026

Hotel Riu Montego Bay - Adults Only - All Inclusive

Hotel Riu Montego Bay - Adults Only - All Inclusive

4 out of 5
Price was $3,254, price is now $1,589 per person
$1,589
per person
Jul 13 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Montego Bay (MBJ)
8.6/10 Excellent! (5,239 reviews)
resort staff clean room, on regular basis at all time

Reviewed on May 12, 2026

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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
$481 nightly
The price is $481 total per night from May 17 to May 18
$481 total
May 17 - May 18
Total with taxes and fees
8.8/10 Excellent! (1,034 reviews)
Great property friendly staff.

Reviewed on May 12, 2026

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
$643 nightly
The price is $643 total per night from May 25 to May 26
$643 total
May 25 - May 26
Total with taxes and fees
9.2/10 Wonderful! (663 reviews)
Lovely hotel ticks all the boxes

Reviewed on May 10, 2026

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
$202 nightly
The price is $222 total per night from May 26 to May 27
$222 total
May 26 - May 27
Total with taxes and fees
8/10 Very Good! (1,757 reviews)
Had a great time.

Reviewed on May 12, 2026

Deja Resort All Inclusive
See all 1,541 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 $704 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.