Middlesex County Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Mike Gauthier

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Silver Creek Resort

Silver Creek Resort

3.5 out of 5
Price was CA $4,604, price is now CA $1,059 per person
CA $1,059
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Montego Bay (MBJ)
7/10 Good! (51 reviews)
The only concern we had was that there is no restaurants within walking distance,

Reviewed on May 20, 2024

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 $5,835, price is now CA $2,660 per person
CA $2,660
per person
Jul 9 - Jul 16
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Montego Bay (MBJ)
9/10 Wonderful! (1,005 reviews)
The resort was absolutely beautiful. If you like to swim in the ocean and enjoy the beach, this is your place. The food was delicious. Make sure you ask for a piña colada. You won’t be disappointed. We will be returning.

Reviewed on May 30, 2026

Ocho Rios Villa at the Palms II

Ocho Rios Villa at the Palms II

3.5 out of 5
Price was CA $3,473, price is now CA $1,765 per person
CA $1,765
per person
Aug 3 - Aug 10
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Montego Bay (MBJ)
9.4/10 Exceptional! (23 reviews)
Clean and family friendly

Reviewed on Apr 3, 2026

Ocho Rios Villa at Coolshade IV

Ocho Rios Villa at Coolshade IV

3.5 out of 5
Price was CA $3,326, price is now CA $1,786 per person
CA $1,786
per person
Aug 3 - Aug 10
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Montego Bay (MBJ)
9.4/10 Exceptional! (10 reviews)
Princess Senses The Mangrove Resort - Adults Only

Princess Senses The Mangrove Resort - Adults Only

4 out of 5
Price was CA $5,116, price is now CA $2,786 per person
CA $2,786
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Montego Bay (MBJ)
9.2/10 Wonderful! (680 reviews)
Great resort with multiple things to do there. All the food options was amazing and the scenery was beautiful

Reviewed on May 29, 2026

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
New Buckfield

New Buckfield

While there might not be top attractions in New Buckfield, you can explore the larger area and discover places like Mahogany Beach and Turtle River Park.

Find hotels in New Buckfield

Ready to book your vacation to Middlesex County?

 

Choose your dates

Middlesex County Hotel Deals

Bahia Principe Escape Runaway Bay - All Inclusive

Bahia Principe Escape Runaway Bay - All Inclusive

4.5 out of 5
Salt Coppers Runaway Bay Saint Ann
The price is CA $509 per night from Jun 30 to Jul 1
CA $509
CA $509 total
Jun 30 - Jul 1
includes taxes & fees
8.4/10 Very Good! (2,323 reviews)
"The reception was welcomed . The hospitality was superb another thing was amazing was the hotel was so clean . The food was great . Sumptuous . I love and I will be back . some day."

Reviewed on May 30, 2026

Bahia Principe Escape Runaway Bay - All Inclusive
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)
"I am very dissatisfied with my experience, I was there for five days and I saw 10 roaches in the room. They were in the bathroom on the sink and all over the room. I notify the from desk when I saw the first three and no one came to spray the room. Also the bathroom had mold in the shower. The room ..."

Reviewed on May 30, 2026

Get rates
Couples Tower Isle All Inclusive
Tiamo Beach Resort and Spa

Tiamo Beach Resort and Spa

4 out of 5
Pear Tree Bottom, Runaway Bay St. Ann
Fully refundableReserve now, pay when you stay
The price is CA $332 per night from Jun 7 to Jun 8
CA $332
CA $383 total
Jun 7 - Jun 8
includes taxes & fees
8.6/10 Excellent! (11 reviews)
"They best part of this hotel is the staff! They are so friendly and welcoming"

Reviewed on May 30, 2026

Tiamo Beach Resort and Spa
See all 2,795 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Middlesex County

Dunn's River Falls

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

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
Caribbean, Jamaica, Runaway Bay, View of a hotel from a sandy beach

Runaway Bay Beach

If a restful vacation is part of your travel plans, Runaway Bay Beach might be the perfect place to seek out during your trip to Runaway Bay. Discover the top-notch restaurants and entertainment choices in this relaxing area.

Runaway Bay Beach

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.

Explore a world of travel with Expedia

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