Middlesex Holidays

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to S$134 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

Top hotels in Middlesex

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 S$615 per night from 14 Jun to 15 Jun
S$615
14 Jun - 15 Jun
includes taxes & fees
8.8/10 Excellent! (175 reviews)
"Good service Good taste good Room clean and nice Kids club will take care kids until 5pm,parents can get set time to enjoyself,they will bring kids to lunch and go to water park too Really nice"

Reviewed on 5 Jun, 2025

Princess Grand Jamaica Resort - All Inclusive
SeaGarden Beach Resort - All Inclusive
SeaGarden Beach Resort - All Inclusive
3.5 out of 5
8 Kent Avenue, Montego Bay, Saint James
Fully refundableReserve now, pay when you stay
The price is S$287 per night from 23 Jun to 24 Jun
S$287
23 Jun - 24 Jun
includes taxes & fees
7.4/10 Good! (2,924 reviews)
"Best stay! Staff was very helpful and friendly!"

Reviewed on 11 Jun, 2025

SeaGarden Beach Resort - All Inclusive
Deja Resort All Inclusive
Deja Resort All Inclusive
3.5 out of 5
92 Gloucester Avenue, Montego Bay, Saint James
Fully refundableReserve now, pay when you stay
The price is S$253 per night from 15 Jun to 16 Jun
S$253
15 Jun - 16 Jun
includes taxes & fees
7.8/10 Good! (1,218 reviews)
"It could be more updated but I always enjoy my time at Deja . I stayed here on 2 separate occasions and had a blast . The scenery outside of the hotel to take picture I loveeeeeee . The food was excellent the jerk chicken and fries omg I could eat it all day"

Reviewed on 10 Jun, 2025

Deja Resort All Inclusive
See all 1,489 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.

Frequently asked questions

How much does a Middlesex holiday package cost?
Offering great value package deals 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.