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 VI

Ocho Rios Villa at Coolshade VI

CA $1,488
per person
Nov 9 - Nov 16
found 20 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Montego Bay (MBJ)
9.8/10 Exceptional! (8 reviews)
This was my 3rd trip to Jamaica, and I wanted to try something different from the expensive all inclusive resorts. After my experience here, I won't be booking resorts again. Getting a whole lot more bang for your buck with the villa booking. The property manager, Mr Davy, was very kind and attentive from the moment I landed, and stayed in touch even after I landed back home to make sure I made it back to my destination safely. He's always a quick whatsapp message or a phone call away if you need anything. The area is very quiet, and the villa was spotless. Highly recommend!

Reviewed on Sep 20, 2022

Sunset at the Palms Resort - Adults Only - All Inclusive

Sunset at the Palms Resort - Adults Only - All Inclusive

CA $2,944
per person
Sep 28 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Montego Bay (MBJ)
9.2/10 Wonderful! (1,009 reviews)
Stayed here a week and couldn’t be happier. The hotel is very cute and outdoorsy (no AC in many places) so you have to be ok with that. The rooms are nice and roomy. The beds are so comfortable! Meals were good, especially at the beach bar. Definitely order the jerk chicken with fries. The staff at the resort were so kind, attentive, respectful and just generally lovely people. There was never an issue of not finding a spot on the beach or pool like you normally experience at larger resorts. I would recommend this hotel to anyone who wants to get away with a couple of books, children free, and have a laid back experience in a beautiful setting.

Reviewed on Aug 26, 2026

Ocho Rios Villa at The Palms

Ocho Rios Villa at The Palms

CA $1,665
per person
Nov 9 - Nov 16
found 20 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) 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

CA $1,676
per person
Nov 15 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Montego Bay (MBJ)
8.4/10 Very good! (3,910 reviews)
My stay at Ocean Eden Bay was enjoyable but I wish some of the amenities of the property were better, like the up charge for lobster and or t bone steak and top shelf alcohol wasn’t necessary. The restaurants closing earlier was a disappointment and only having one restaurant to choose from late night, the extra room charges for room service when we’re at an all inclusive resort was another disappointment. Over all it was a nice/peaceful resort, with very respectful staff.

Reviewed on Aug 28, 2026

Retreat Plantation House

Retreat Plantation House

CA $1,604
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Montego Bay (MBJ)
10/10 Exceptional! (1 review)
Totally enjoyed our stay at Retreat Plantation, home away from home , excellent management, Robin and his housekeepers we're L extremely pleasant. We would definitely go again!

Reviewed on Feb 17, 2017

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

Industry Cove Green Island Hanover
CA $582
CA $582 total
Sep 27 - Sep 28
includes taxes & fees
9/10 Wonderful! (1,675 reviews)
"The stay was a 10/10. Will definitely be back."

Reviewed on Aug 28, 2026

Princess Grand Jamaica Resort - All Inclusive
Princess Senses The Mangrove Resort - Adults Only

Princess Senses The Mangrove Resort - Adults Only

Industry Cove Green Island Hanover
CA $754
CA $754 total
Sep 1 - Sep 2
includes taxes & fees
Princess Senses The Mangrove Resort - Adults Only
Deja Resort All Inclusive

Deja Resort All Inclusive

92 Gloucester Avenue Montego Bay Saint James
Fully refundableReserve now, pay when you stay
CA $290
CA $342 total
Sep 2 - Sep 3
includes taxes & fees
8.2/10 Very good! (1,953 reviews)
"The room was clean, the staff was amazing , the food was delicious and I look forward to visiting again next year."

Reviewed on Aug 28, 2026

Deja Resort All Inclusive
See all 1,558 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?
You'll find cheap prices from CA $1,488 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.