Middlesex Holidays from AU$1,661

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to AU$703 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Alamanda Cottage at Serenity
Casa Marina Montego Bay at Seawind
Hotel Riu Montego Bay - Adults Only - All Inclusive
suites in Montego Bay Jamaica
Hotel Riu Palace Jamaica - Adults Only - All Inclusive

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$658 per night from 20 Aug to 21 Aug
AU$658
20 Aug - 21 Aug
includes taxes & fees
8.6/10 Excellent! (440 reviews)
"Everything about the property was beautiful!"

Reviewed on 3 Aug. 2025

Princess Grand Jamaica Resort - All Inclusive
S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel

S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel

4 out of 5
7 Jimmy Cliff Blvd, Montego Bay, Saint James
The price is AU$572 per night from 3 Sept to 4 Sept
AU$572
3 Sept - 4 Sept
includes taxes & fees
9.4/10 Exceptional! (2,011 reviews)
"Loved the location of this property. Also enjoyed the food, service and all around vibes. Close to everything and felt safe to leave the resort and walk around."

Reviewed on 3 Aug. 2025

S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel
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$785 per night from 26 Aug to 27 Aug
AU$785
26 Aug - 27 Aug
includes taxes & fees
9.2/10 Wonderful! (299 reviews)
"Excellent choice!"

Reviewed on 3 Aug. 2025

Princess Senses The Mangrove Resort - Adults Only
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.

Frequently asked questions

How much does a Middlesex holiday package cost?
Offering great value package deals from AU$1,661 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.

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