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.
Ocho Rios Villa at Coolshade

Ocho Rios Villa at Coolshade

3.5 out of 5
Price was CA $2,707, price is now CA $1,358 per person
CA $1,358
per person
May 14 - May 21
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to Montego Bay (MBJ)
6/10 (18 reviews)
The host was wonderful and quite responsive. I will definately stay again and highly recomend.

Reviewed on Mar 18, 2023

Ocho Rios Villa at the Palms II

Ocho Rios Villa at the Palms II

3.5 out of 5
Price was CA $3,260, price is now CA $1,576 per person
CA $1,576
per person
May 14 - May 21
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to Montego Bay (MBJ)
8.6/10 Excellent! (25 reviews)
The property is huge and maybe we were a little unprepared for that but it was a very pleasant experience and I am glad we gave it a crack versus the big names. The host Ms. Powell took excellent care of us and was there from the moment we booked to guide and advise us. Thanks for an amazing stay are your villa.

Reviewed on Apr 25, 2023

Ocho Rios Villa at Coolshade X

Ocho Rios Villa at Coolshade X

3.5 out of 5
Price was CA $3,178, price is now CA $1,563 per person
CA $1,563
per person
May 14 - May 21
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to Montego Bay (MBJ)
9.6/10 Exceptional! (5 reviews)
Ocho Rios Tranquility at Coolshade VII

Ocho Rios Tranquility at Coolshade VII

3 out of 5
Price was CA $3,058, price is now CA $1,541 per person
CA $1,541
per person
May 14 - May 21
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to Montego Bay (MBJ)
No reviews
Ocho Rios Villa at Coolshade XI

Ocho Rios Villa at Coolshade XI

3.5 out of 5
Price was CA $2,944, price is now CA $1,494 per person
CA $1,494
per person
May 14 - May 21
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to Montego Bay (MBJ)
8.6/10 Excellent! (9 reviews)
Very good stay in Coolshade. Lorraine the manager was very attentive to our needs and helped to organize transportation and a helper to make our beds and meals for us.

Reviewed on Jan 27, 2019

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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
Aerial view of Ocho Rios, Jamaica

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 Fort Clarence Beach.

Find hotels in Caribbean Estates

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Middlesex County Hotel Deals

Couples Tower Isle All Inclusive

Couples Tower Isle All Inclusive

4.5 out of 5
Tower Isle Tower Isle Saint Mary
9.2/10 Wonderful! (1,003 reviews)
Everyone and everything was amazing

Reviewed on Feb 13, 2026

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Couples Tower Isle 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
8.4/10 Very Good! (2,377 reviews)
Great place

Reviewed on Dec 10, 2025

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Bahia Principe Luxury Runaway Bay - Adults Only - All Inclusive
Jewel Paradise Cove Adult Beach Resort & Spa – All Inclusive

Jewel Paradise Cove Adult Beach Resort & Spa – All Inclusive

4 out of 5
Paradise Cove Drive Runaway Bay Saint Ann
8.2/10 Very Good! (1,001 reviews)
Jewel Paradise Cove exceeded my expectations. Beautiful ocean views, peaceful atmosphere, amazing staff, and delicious food. The perfect place to unwind in Ocho Rios. Highly recommend!

Reviewed on Feb 12, 2026

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Jewel Paradise Cove Adult Beach Resort & Spa – All Inclusive
See all 2,740 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

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

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

Mystic Mountain
Pond turtle on a log. Gilchrist Blue Springs State Park, Florida, US

Turtle River Park

Enjoy the beautiful waterfalls and explore Turtle River Park, a lovely green space in Ocho Rios. Check out the shops and top-notch restaurants in this romantic area.

Turtle River Park

Frequently asked questions

Can I cancel my flight booking to Middlesex County due to COVID-19?
Our handy Customer Service Portal is your one-stop shop for most travel questions, including about flight cancellations and changes due to COVID-19. For greater peace of mind, we recommend looking over the terms and conditions of your preferred airline before booking your next flight.
What's the best way to find cheap flights to Middlesex County that have flexible change policies?
Search for cheap fares to Middlesex County, then tick the "No change fee" box below the "Flexible change policies" filter. From then on it's smooth sailing. We appreciate that plans change and flexibility is important, so you can book with confidence with Expedia.
What are some of the general tips for travelers to Middlesex County during the COVID-19 outbreak?
COVID-19 has resulted in big changes to how we travel. If you plan to visit Middlesex County, these tips will help you navigate this new traveling reality:
  • Before booking anything, check if any travel restrictions apply — in both your destination and origin. Get up-to-date information by reviewing government travel advisories.
  • You're required to wear a face mask throughout your travel experience, including at security checkpoints. Be prepared to lower your mask to verify your identity when asked by a TSA employee.
  • Instead of handing a TSA officer your boarding pass, position it directly on the scanner yourself. Then, hold it up for inspection.
  • TSA is now allowing passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on luggage. This will have to be removed from your bag to be screened.
  • Place any personal items (e.g, keys, phone and wallet) in your carry-on instead of a bin to minimize handling during the screening process.
  • Transport your food items in a clear plastic bag and also place them in a screening bin. Keeping food separate from your carry-on makes it less likely that a TSA agent will need to open and touch your bag for inspection.

Which airlines fly to Middlesex County?
American Airlines is a popular airline servicing Middlesex County. Look up airfares to Sir Donald Sangster Intl. Airport (MBJ) and you'll have 277 American Airlines flights each month to select from.
How can I find cheap tickets to Middlesex County?
For the best deal to Middlesex County, book ahead of time. Also use Expedia's handy "flexible dates" link at the top of your search results. This will compare prices for similar time frames. In the last seven days, was the lowest price for a flight to Middlesex County.
How much is a flight to Middlesex County?
One-way flights leaving () sold for as little as in the last seven days. During this time, the price of a return journey to Middlesex County varied between and . If you find a fantastic deal, book fast — these prices don't hang around.
What are the most popular airports to fly into in Middlesex County?
Pack your bags and jet into Sir Donald Sangster Intl. Airport (MBJ), Middlesex County's major flight hub. Book a fare on one of the 1063 flights that touch down at this top destination each month.
When is the cheapest time to fly to Middlesex County?
If you'd prefer to spend your vacation dollars getting to know Middlesex County rather than on your flight there, leave earlier in the week. The most cost-effective day to travel is generally Tuesday, with Monday close behind. With many folks traveling on the weekend, Saturday often has the costliest fares.
How much is a plane ticket to Middlesex County?
In the last seven days, ticket prices to Middlesex County varied from to .
Which airlines with flights to Middlesex County employ COVID-19 cleanliness policies?
In response to the ongoing COVID-19 pandemic, airlines have rolled out additional actions and measures to help their passengers and staff get back in the skies. Here are a few examples:
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • JetBlue - this airline is known for keeping the middle seat empty and capped capacity flights.
  • Southwest Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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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.