Middlesex Holidays
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- Better togetherSave up to €900 when you book a flight and hotel together*
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Top Flight + Hotel Deals in Middlesex
Price found within the past 48 hours. Click for updated prices.
Sunset at the Palms Resort - Adults Only - All Inclusive
€1,687
per person
3 Oct - 10 Oct
found 15 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
9.2/10 Wonderful! (1,009 reviews)
Stayed here a week and couldn’t be happier. The hotel is very cute and outdoorsy (no AC in many places) so you have to be ok with that. The rooms are nice and roomy. The beds are so comfortable! Meals were good, especially at the beach bar. Definitely order the jerk chicken with fries. The staff at the resort were so kind, attentive, respectful and just generally lovely people. There was never an issue of not finding a spot on the beach or pool like you normally experience at larger resorts. I would recommend this hotel to anyone who wants to get away with a couple of books, children free, and have a laid back experience in a beautiful setting.
Reviewed on 26 Aug 2026
Moon Palace Jamaica – All Inclusive
€2,338
per person
3 Oct - 10 Oct
found 15 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
8.4/10 Very good! (2,140 reviews)
Me and my family had a great time! The staff were great! Big up to Kathy at the guest service desk. Tash, who set up our romantic anniversary spa treatment. Thank you!!! The ladies who work at the sushi bar. Also Ash! Our vacation was Awesome with these ladies assistance. Great customer service!!!!!
Reviewed on 29 Aug 2026
Top hotels in Middlesex
Princess Grand Jamaica Resort - All Inclusive
Industry Cove Green Island Hanover
€401
30 Aug - 31 Aug
includes taxes & fees
Princess Senses The Mangrove Resort - Adults Only
Industry Cove Green Island Hanover
€467
31 Aug - 1 Sept
includes taxes & fees
9.2/10 Wonderful! (955 reviews)
"Everything was beautiful, exceptionally friendly staff, clean rooms, wonderful eateries."
Reviewed on 29 Aug 2026
Deja Resort All Inclusive
92 Gloucester Avenue Montego Bay Saint James
Fully refundableReserve now, pay when you stay
€216
1 Sept - 2 Sept
includes taxes & fees
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 €1,452 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.
