Middlesex Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Middlesex
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Montego Bay - Adults Only - All Inclusive
€1,578
per person
4 Jan - 8 Jan
found 11 hours ago
Return flight included
Chicago (ORD) to Montego Bay (MBJ)
8.6/10 Excellent! (5,563 reviews)
My stay here was better than I expected! Food was amazing (I miss it already), staff were of perfect assistance, and everywhere was clean! And most importantly I felt very safe :)
Reviewed on 13 Oct 2026
Bahia Principe Escape Runaway Bay - Hyatt Inclusive Collection - Adults Only - All Inclusive
€1,501
per person
4 Jan - 8 Jan
found 11 hours ago
Return flight included
Chicago (ORD) to Montego Bay (MBJ)
8.4/10 Very good! (2,519 reviews)
room needs better ventilation and shower leaks water seal around shower needs attention.
Reviewed on 13 Oct 2026
Top hotels in Middlesex
Princess Grand Jamaica Resort - All Inclusive
Industry Cove Green Island Hanover
€417
15 Oct - 16 Oct
includes taxes & fees
Princess Senses The Mangrove Resort - Adults Only
Industry Cove Green Island Hanover
€497
15 Oct - 16 Oct
includes taxes & fees
9.4/10 Exceptional! (1,094 reviews)
"The rooms are beautiful! I’m in the O’Club. Tons of activities to do. However, the customer service is terrible. The internet has been out 3 of the 4 days I’ve been here, there are rolling blackouts so I wake up hot and sweating in the middle of the night. Everytime I order food at a restaurant, ..."
Reviewed on 14 Oct 2026
Deja Resort All Inclusive
92 Gloucester Avenue Montego Bay Saint James
Fully refundableReserve now, pay when you stay
€225
19 Oct - 20 Oct
includes taxes & fees
8.2/10 Very good! (2,004 reviews)
"Nice property,conveniently located, reasonable rate for the amenities they have."
Reviewed on 13 Oct 2026
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 €1,392 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?
- 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.
- 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.
- 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.
- 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.
