Middlesex Holidays from AU$1,865

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Your Middlesex Holiday

Our Middlesex holiday packages let you customise your own adventure. Tailor your getaway to suit your interests and needs and make the most of your time in this lively city. If visiting the sights is a priority during your trip to Middlesex, be sure to check out famous attractions like Hanover Museum and Headland. Stop daydreaming and start adventuring. Browse the many options on Expedia today and put your Middlesex holiday plans into gear!

The Latest Middlesex Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Ocean Coral Spring - All Inclusive

Ocean Coral Spring - All Inclusive

5 out of 5
Save 100% on your flight
Price was AU$3,131, price is now AU$1,865 per person
AU$1,865
per person
9 Sept - 13 Sept
found 10 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
8.4/10 Very good! (4,136 reviews)
I had a great time. I daughter enjoyed the water park and she always took part in Some of the resort activities. Joseph Thomas was a great entertainer we did pool aerobics and went bowling and had lots of fun.

Reviewed on 9 July 2026

Sunset at the Palms Resort - Adults Only - All Inclusive

Sunset at the Palms Resort - Adults Only - All Inclusive

4.5 out of 5
Save 100% on your flight
Price was AU$4,192, price is now AU$2,146 per person
AU$2,146
per person
9 Sept - 13 Sept
found 10 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
9.2/10 Wonderful! (1,003 reviews)
The most relaxing resort stay I ever had in the Caribbean. No noise. Jungle setting was unique. Rooms (bungalow) was awesome experience. Staff was not in your face all the time and was there only when you wanted or needed them. Swim up bar was just the right size and setting for us. Kudos. I try all kinds of resorts but I may even be back here sooner rather than later.

Reviewed on 8 July 2026

Hotel Riu Montego Bay - Adults Only - All Inclusive

Hotel Riu Montego Bay - Adults Only - All Inclusive

4 out of 5
Save 100% on your flight
Price was AU$4,010, price is now AU$2,316 per person
AU$2,316
per person
12 Aug - 16 Aug
found 9 hours ago
Return flight included
New York (NYC) to Montego Bay (MBJ)
8.6/10 Excellent! (5,319 reviews)
The beach was clean and well kept. You don't need to buy anything sold on the beach or outside of the property.

Reviewed on 9 July 2026

Ocean Eden Bay - Adults Only - All inclusive

Ocean Eden Bay - Adults Only - All inclusive

5 out of 5
Save 100% on your flight
Price was AU$3,494, price is now AU$2,027 per person
AU$2,027
per person
9 Sept - 13 Sept
found 10 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
8.4/10 Very good! (3,873 reviews)
I thoroughly enjoyed my stay, would refer, and willing to return for another visit. Resort events were most enjoyable. Not to mention the athletic aerobic pool instructor.

Reviewed on 10 July 2026

Princess Senses The Mangrove Resort - Adults Only

Princess Senses The Mangrove Resort - Adults Only

4 out of 5
Save 100% on your flight
Price was AU$3,657, price is now AU$2,264 per person
AU$2,264
per person
9 Sept - 13 Sept
found 10 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
9.2/10 Wonderful! (790 reviews)
We enjoyed and would definitely vacation here again

Reviewed on 10 July 2026

Middlesex Holiday

Middlesex Essential Information

Language
English
Currency
Jamaican dollars
Closest Airport
Sir Donald Sangster Intl. Airport (MBJ)
Max Temp Winter
27ºC
Max Temp Summer
29ºC
Top Sights
Half Moon Beach, Tryall Golf Club and Hanover Museum

Our pick of the best 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
The price is AU$777 per night from 13 July to 14 July
AU$777
13 July - 14 July
includes taxes & fees
9/10 Wonderful! (1,367 reviews)
"🙌"

Reviewed on 10 July 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
The price is AU$880 per night from 29 July to 30 July
AU$880
29 July - 30 July
includes taxes & fees
9.2/10 Wonderful! (823 reviews)
"We enjoyed and would definitely vacation here again"

Reviewed on 10 July 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
The price is AU$387 per night from 10 Aug to 11 Aug
AU$387
10 Aug - 11 Aug
includes taxes & fees
8.2/10 Very good! (1,872 reviews)
"Great"

Reviewed on 10 July 2026

Deja Resort All Inclusive
See all 1,536 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
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beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Middlesex holiday package cost?
Offering great value package deals from AU$1,865 on Expedia, you'll be thrilled with how little a holiday to Middlesex costs! Our packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Middlesex?
You can generally find lower prices and better availability in January, February and September. Check out our cheap Middlesex holiday packages and you could get some excellent off-season deals.
How many days is enough for Middlesex?
With a well-planned itinerary, you can easily tick off the most popular Middlesex sights in a few days. But if you'd like to explore off the beaten track or go on day trips, think about booking your Middlesex holiday 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 holiday package as early as possible.
Is it cheaper to book a Middlesex holiday as a package?
You can enjoy significant savings on your Middlesex getaway by booking a customised holiday 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 holiday package to Middlesex?
If you're planning a spur-of-the-moment Middlesex holiday, 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.
How to plan a trip to Middlesex?

  1. Choose when to go: Check your schedule and get your bags packed. Your preferred time of year and the type of activities on offer will also help you decide when to escape to Middlesex.
  2. Budget wisely: Besides the cost of your hotel, you'll need to factor in other expenses. These include food, flights and transportation. Also, set aside some extra funds for unexpected costs that could arise during your trip to Middlesex.
  3. Decide how long to go for: Now that you're more familiar with Middlesex, you can figure out the perfect length of your holiday. Create a rough plan and give yourself enough time to cover everything you want to see.
  4. Bundle your accommodation and airfare: Once you've settled on your dates and duration, lock in the perfect Middlesex holiday package for you.

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