Middlesex County Vacation Packages

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Your Middlesex County Vacation

Lock in a Middlesex County vacation package and enjoy all the places your adventurous soul takes you. This destination has plenty to offer, including its culture, walking trails, history, and much more. A trip to Middlesex County wouldn't be complete without experiencing some of its leading cities, starting with Ocho Rios. Some of the most popular attractions here include Dunn's River Falls and Turtle Beach. Mandeville should also be on the itineraries of all Middlesex County travellers. Visitors to this destination love Mega Mart and Manchester Parish Court. Expedia has flights, hotels and all your other travel needs to help you curate your own customized Middlesex County vacation today.

Top Middlesex County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Ocean Coral Spring - All Inclusive

Ocean Coral Spring - All Inclusive

5 out of 5
Price was CA $3,594, price is now CA $1,683 per person
CA $1,683
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Montego Bay (MBJ)
8.2/10 Very Good! (3,765 reviews)
Great place to stay. Lovely staff

Reviewed on Aug. 20, 2025

Princess Senses The Mangrove Resort - Adults Only

Princess Senses The Mangrove Resort - Adults Only

4 out of 5
Price was CA $9,670, price is now CA $2,827 per person
CA $2,827
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Montego Bay (MBJ)
9.2/10 Wonderful! (300 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 Aug. 20, 2025

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 $4,393, price is now CA $1,864 per person
CA $1,864
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Montego Bay (MBJ)
9.2/10 Wonderful! (1,003 reviews)
⸻ “Beautiful property! It truly feels like you are surrounded by nature — quiet, romantic, and perfect for relaxing. The service and food are excellent. Breakfast could be improved since it’s always the same, but they do have a nice coffee bar and mimosas! The Chef is so dedicated to sharing the best of their culture that it feels like having your own personal chef. I can’t wait to come back! And the beach… ahhhh, simply the best. They also offer a 6-hour catamaran trip that you will absolutely love.”

Reviewed on Aug. 19, 2025

Ocho Rios Villa at The Palms

Ocho Rios Villa at The Palms

3 out of 5
Price was CA $4,004, price is now CA $1,729 per person
CA $1,729
per person
Oct 24 - Oct 31
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Montego Bay (MBJ)
10/10 Exceptional! (2 reviews)
The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive

The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive

5 out of 5
Price was CA $18,101, price is now CA $8,380 per person
CA $8,380
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Montego Bay (MBJ)
10/10 Exceptional! (2 reviews)
Excellent Resort, especially all the excellence club amenities

Reviewed on May 1, 2025

Where to stay in Middlesex County

Find the best Middlesex County areas and neighborhoods for the activities you enjoy most. Learn more about Middlesex County
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Caribbean Estates

While there might not be top attractions in Caribbean Estates, you can explore the larger area and discover places like Sovereign Village Mall and Hellshire Beach.

Find hotels in Caribbean Estates

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Middlesex County Hotel Deals

Bahia Principe Grand Jamaica - All Inclusive

Bahia Principe Grand Jamaica - All Inclusive

4 out of 5
Salt Coppers Villa, Runaway Bay, Saint Ann
The price is CA $374 per night from Sep 19 to Sep 20
CA $374
CA $374 total
Sep 19 - Sep 20
includes taxes & fees
7.4/10 Good! (2,560 reviews)
"Easy access to all amenities"

Reviewed on Aug. 20, 2025

Bahia Principe Grand Jamaica - All Inclusive
Bahia Principe Luxury Runaway Bay - Adults Only - All Inclusive

Bahia Principe Luxury Runaway Bay - Adults Only - All Inclusive

4.5 out of 5
Salt Coppers, Runaway Bay, Saint Ann
The price is CA $448 per night from Sep 20 to Sep 21
CA $448
CA $448 total
Sep 20 - Sep 21
includes taxes & fees
8.2/10 Very Good! (2,566 reviews)
"Food choice was good Pool and entertainment was excellent."

Reviewed on Aug. 12, 2025

Bahia Principe Luxury Runaway Bay - Adults Only - All Inclusive
Couples Tower Isle All Inclusive

Couples Tower Isle All Inclusive

4.5 out of 5
Tower Isle, Ocho Rios, Tower Isle, Saint Mary
9.2/10 Wonderful! (1,008 reviews)
"Property was amazing, relaxing and courtesy…"

Reviewed on Aug. 19, 2025

Get rates
Couples Tower Isle All Inclusive
See all 2,573 properties in Middlesex County
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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Discover the most popular places to visit in Middlesex County

Dunn\'s River Falls which includes a waterfall and rainforest

Dunn's River Falls

4.5/5(37 reviews)

The natural mineral pools under these beautiful terracing waterfalls are a refreshing treat after a hike through this tropical paradise.

Dunn's River Falls
Mystic Mountain which includes a coastal town and a bay or harbour

Mystic Mountain

4.5/5(16 reviews)

Enjoy the rainforest at top speed by gliding down a huge hill in a bobsled, a fun activity for the whole family.

Mystic Mountain
Green Grotto Caves showing interior views and caves

Green Grotto Caves

4.5/5(10 reviews)

Discover an underground world with rock formations, light holes, bats and a subterranean lake in a setting that has played a role in local history for centuries.

Green Grotto Caves

Frequently asked questions

How much does a Middlesex County vacation package cost?
Starting from a low CA $1,683, a package is your passport to inexpensive travel. Create your own Middlesex County trip by selecting from our comprehensive range of flights, hotels and rental cars.
How do I get a cheap travel package to Middlesex County?
It's easy. Just bundle. Flights, rental cars and hotels — combine whatever you need into a Middlesex County vacation package to save a pile of cash. Score even bigger bargains when you add extras such as activities or tours to your booking. But that's not the only impressive part. You have the freedom to put together your trip your way. We offer more than 550 airlines and 1,000,000 hotels around the world, so that everyone has a chance to travel and live out those vacation fantasies.
Where should I stay in Middlesex County?
Ocho Rios is a great place to explore. It lures many people who come to explore its major sights, like Dunns River Falls and Turtle Beach.
What are the top hotels in Middlesex County?
When it comes to hotels in Ocho Rios, Riu Ocho Rios and Bahia Principe Luxury Runaway Bay are two excellent options. If you're also staying in St. Anns Bay, Bahia Principe Grand Jamaica and Moon Palace Jamaica will make you feel right at home.
How far in advance should I book my Middlesex County vacation?
Travelers can normally browse international flights on Expedia within 12 months of the departure date. Booking at the last minute? With a stroke of luck, it's still possible to nab an affordable ticket only weeks before your flight.
What does an Expedia Middlesex County travel package include?
Hotels, flights and car rentals — we connect you to the very best deals. All you'll have to do is decide on your ideal combination. After you've made your booking, you can add on the fun stuff like tours and experiences. Our travel packages make it simple to customize an exciting Middlesex County escape.
What should I know before booking a Middlesex County travel package?
You can save big by combining your hotels, airfares and rental cars. Once you've created your package, add on fun stuff like sightseeing tours or experiences. Your next awesome vacation is only a couple of clicks away.
Can I choose my airline with a Middlesex County Expedia vacation package?
Yes, you sure can. Expedia has access to more than 550 partner airlines globally, so go with the carrier that suits your travel preferences.
If I'm not able to travel, can I cancel my Middlesex County vacation package?
We get it — life sometimes gets in the way of your plans. If you've booked a Middlesex County vacation package and need to cancel or amend it, we can help. We suggest taking a look at our Customer Service Portal first for information. But in general, if you've booked your package in the last 24 hours, you may be able to amend or cancel your itinerary for free. If it's been more than 24 hours, your airline, hotel or car rental company may impose a charge.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.