Middlesex Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to SAR 390 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

Find the Best Middlesex Vacation Packages

Middlesex Hotel Deals

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 SAR 1,251 per night from Sep 22 to Sep 23
SAR 1,251
SAR 1,454 total
22 Sep - 23 Sep
includes taxes & fees
9.4/10 Exceptional! (2,037 reviews)
"I really love the room and the view from the balcony of the beach the full options was great Transportation was good I would definitely go again"

Reviewed on 21 August 2025

S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel
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 SAR 1,689 per night from Sep 1 to Sep 2
SAR 1,689
SAR 1,689 total
1 Sep - 2 Sep
includes taxes & fees
8.6/10 Excellent! (526 reviews)
"Great experience"

Reviewed on 21 August 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 SAR 2,505 per night from Sep 5 to Sep 6
SAR 2,505
SAR 2,505 total
5 Sep - 6 Sep
includes taxes & fees
9/10 Wonderful! (340 reviews)
"I love the fact that my room was a corner room and I had the best room out of a group of 8 with a bar and hot tub"

Reviewed on 20 August 2025

Princess Senses The Mangrove Resort - Adults Only
See all 1,487 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 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.