Middlesex Vacation Packages

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Your Middlesex Vacation

The adventure-filled city of Middlesex is calling your name. Uncover both its hidden gems and highlights with a Middlesex vacation package that's tailored to you. There's loads to see and do during a trip to Middlesex, including Hanover Museum and Headland. Stop daydreaming and start traveling. Explore the multitude of options on Expedia today and put your Middlesex vacation plans into gear!

Top Middlesex Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Ocho Rios Villa at Coolshade

Ocho Rios Villa at Coolshade

3.5 out of 5
Price was CA $2,805, price is now CA $1,444 per person
CA $1,444
per person
Aug 17 - Aug 24
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Montego Bay (MBJ)
9.8/10 Exceptional! (10 reviews)
Clean house with ac in each room very cozy and private area great security and safe environment. Love the grocery store across the street good food. You would need to have a vehicle to enjoy it like I did, i rented a Kia. Nice pool and gym has new equipment being installed 👍

Reviewed on Jun 6, 2026

Sunset at the Palms Resort - Adults Only - All Inclusive

Sunset at the Palms Resort - Adults Only - All Inclusive

4.5 out of 5
Price was CA $6,088, price is now CA $2,941 per person
CA $2,941
per person
Sep 14 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Montego Bay (MBJ)
9.2/10 Wonderful! (1,003 reviews)
Had a wonderful time!

Reviewed on Jul 13, 2026

Ocho Rios Villa at The Palms

Ocho Rios Villa at The Palms

3 out of 5
Price was CA $4,087, price is now CA $2,093 per person
CA $2,093
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Montego Bay (MBJ)
10/10 Exceptional! (2 reviews)
All staff were professional, courteous and friendly. They all went out of their way to grant your requests. The ambience is very nice. The electrical outlets on the patio didn't always work. Had to be creative in getting plugs to stay in. They also need to upgrade from 110v to 220v. Just kidding, but they should have something for travelers from Europe. Internet service was pretty good. Everyone in my group were pleased and would return. The tour setup for us by the manager was fun!!!! Good people, fantastic accommodations. Recommended...

Reviewed on May 8, 2019

Ocean Eden Bay - Adults Only - All inclusive

Ocean Eden Bay - Adults Only - All inclusive

5 out of 5
Price was CA $4,661, price is now CA $2,459 per person
CA $2,459
per person
Sep 14 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Montego Bay (MBJ)
8.4/10 Very good! (3,873 reviews)
The buffet food was not good need more entertainment at the pool need more alcohol selections for the people that’s not in premier and to have 24 hour room service

Reviewed on Jul 13, 2026

Ocean Coral Spring - All Inclusive

Ocean Coral Spring - All Inclusive

5 out of 5
Price was CA $4,164, price is now CA $2,234 per person
CA $2,234
per person
Sep 14 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Montego Bay (MBJ)
8.4/10 Very good! (4,136 reviews)
Really great stay! The room upgrade was a plus.

Reviewed on Jul 13, 2026

Ready to book your vacation to Middlesex?

 

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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 CA $699 per night from Aug 12 to Aug 13
CA $699
CA $699 total
Aug 12 - Aug 13
includes taxes & fees
9/10 Wonderful! (1,390 reviews)
"Amazing hotel"

Reviewed on Jul 13, 2026

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 CA $865 per night from Jul 27 to Jul 28
CA $865
CA $865 total
Jul 27 - Jul 28
includes taxes & fees
9.2/10 Wonderful! (828 reviews)
"Everything was amazing. Already planning my next stay."

Reviewed on Jul 13, 2026

Princess Senses The Mangrove Resort - Adults Only
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 CA $323 per night from Aug 10 to Aug 11
CA $323
CA $380 total
Aug 10 - Aug 11
includes taxes & fees
8.2/10 Very good! (1,887 reviews)
"I liked this resort. The safe are very friendly and the accommodate us with what we needed. I will definitely come back and stay here"

Reviewed on Jul 13, 2026

Deja Resort All Inclusive
See all 1,541 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.
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Frequently asked questions

How much does a Middlesex vacation package cost?
You'll find cheap prices from CA $1,444 on Expedia for your Middlesex getaway. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Middlesex costs.
What are the cheapest months to go to Middlesex?
January, February and September are great times to search for cheap Middlesex vacation packages. Travelling in quieter months means you can generally find better prices on flights and accommodations.
How many days is enough for Middlesex?
The ideal length of your Middlesex vacation depends on what you'd like to do and see. Typically, a few days to a week will give you time to go to all the major attractions and explore some hidden gems along the way.
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 adventure for midweek, or browse for Middlesex package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Middlesex vacation as a package?
You can enjoy significant savings on your Middlesex break by booking a personalized vacation package. Check the "Package" heading, then select your travel dates and destination to browse some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Middlesex?
Land incredible discounts by reserving your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Middlesex escape.
How to plan a trip to Middlesex?

  1. Pick your travel dates: What you'd like to do in Middlesex and your preferred season can help you decide when to get away.
  2. Calculate your budget: Make sure you have enough money to cover everything from transportation and food to activities and flights. Your hotel will probably be the largest expense during your trip to Middlesex.
  3. Decide how long to go away for: Now that you're more familiar with Middlesex, you can work out the ideal length of your break. Put together a draft plan and give yourself enough time to cover everything you want to see.
  4. Combine your accommodations and airfare: Once you've settled on your travel dates and duration, lock in the perfect Middlesex vacation package for you.

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