Middlesex Vacations

Book a Hotel + Flight or Car together to unlock savings

    deals illustration
    Better together
    Save up to NT$5,067 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

Find the Best Middlesex Vacation Packages

Middlesex Hotel Deals

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 NT$14,242 per night from Jul 5 to Jul 6
NT$14,242
NT$14,242 total
Jul 5 - Jul 6
includes taxes & fees
8.8/10 Excellent! (251 reviews)
"Staff were amazing. Food was good. Water park was fun. My only complaint was not enough beach/water. Only a very small area to swim that was rather shallow. Other than that, this place is amazing."

Reviewed on 2025/7/3

Princess Grand Jamaica 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 NT$5,931 per night from Jul 21 to Jul 22
NT$5,931
NT$6,997 total
Jul 21 - Jul 22
includes taxes & fees
7.8/10 Good! (1,242 reviews)
"We had a awesome time and we will do it all over again in a heartbeat the food was excellent lots of choices, Loretta the entertainment cordenator was excellent, the one person that went above and beyond was Crystal from the dining room u all should be very proud to have her as an employee she raised ..."

Reviewed on 2025/6/27

Deja Resort All Inclusive
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 NT$12,377 per night from Jul 8 to Jul 9
NT$12,377
NT$14,349 total
Jul 8 - Jul 9
includes taxes & fees
9.4/10 Exceptional! (1,953 reviews)
"Staff is super friendly. Specifically Tiffany at the front desk. She was always very informative and always greeted you with a smile. The food was amazing and the over all vibe was chill and relaxing. The drinks are on point. Highly recommend."

Reviewed on 2025/6/30

S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel
See all 1,479 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.