Middlesex Trips (flight + hotel)

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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 P28,161 per night from Aug 20 to Aug 21
P28,161
P28,161 total
Aug 20 - Aug 21
includes taxes & fees
8.6/10 Excellent! (429 reviews)
"The property is beautiful, but the staff is the BEST part! Dhalia made sure my room was pristine and she was was so congenial. I loved speaking with her in the morning. My girl Antoinette took great care of me in the cabanas on the Princes side. She was my bestie. Rakeesh my bartender by the pool ..."

Reviewed on Aug 1, 2025

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 P28,648 per night from Aug 10 to Aug 11
P28,648
P28,648 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (294 reviews)
"Comparable to most other all inclusives on the island but on the pricier end."

Reviewed on Aug 2, 2025

Princess Senses The Mangrove Resort - Adults Only
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
Fully refundableReserve now, pay when you stay
The price is P19,911 per night from Sep 1 to Sep 2
P19,911
P23,130 total
Sep 1 - Sep 2
includes taxes & fees
9.4/10 Exceptional! (1,998 reviews)
"N/A"

Reviewed on Jul 31, 2025

S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel
See all 1,466 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 vacation package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a vacation to Middlesex costs! Our packages simplify travel planning and maximize 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 vacation 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 vacation 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 vacation package as early as possible.
Is it cheaper to book a Middlesex vacation as a package?
You can enjoy significant savings on your Middlesex getaway by booking a customized vacation 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 vacation package to Middlesex?
If you're planning a spur-of-the-moment Middlesex vacation, 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 vacation. Create a rough plan and give yourself enough time to cover everything you want to see.
  4. Bundle your accommodations and airfare: Once you've settled on your dates and duration, lock in the perfect Middlesex vacation package for you.

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