Middlesex County Vacations from ₩1,486,082

Book a Hotel + Flight or Car together to unlock savings

Photo by Mike Gauthier

  • Plan, book, travel with confidence

  • Better together

    Save up to ₩234,741 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

The Latest Middlesex County Vacation Packages

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

Ocho Rios Tranquility at Coolshade VII

3 out of 5
Save 100% on your flight
Price was ₩2,890,745, price is now ₩1,486,082 per person
₩1,486,082
per person
Apr 26 - May 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Montego Bay (MBJ)
No reviews
Ocho Rios Villa at the Palms II

Ocho Rios Villa at the Palms II

3.5 out of 5
Save 100% on your flight
Price was ₩3,073,548, price is now ₩1,513,138 per person
₩1,513,138
per person
Apr 26 - May 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Montego Bay (MBJ)
9.4/10 Exceptional! (22 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
Save 100% on your flight
Price was ₩2,989,725, price is now ₩1,503,096 per person
₩1,503,096
per person
Apr 26 - May 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Montego Bay (MBJ)
9.6/10 Exceptional! (5 reviews)
Ocean Eden Bay - Adults Only - All inclusive

Ocean Eden Bay - Adults Only - All inclusive

5 out of 5
Price was ₩4,829,460, price is now ₩2,438,499 per person
₩2,438,499
per person
Apr 26 - May 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Montego Bay (MBJ)
8.4/10 Very Good! (3,718 reviews)
The resort is 5 stars. From check-in, to the room, food, entertainment & customer service, you get the best. I recommend this resort to those who enjoy an adults all inclusive resort.

Reviewed on Mar 22, 2026

Ocho Rios Getaway Villa at The Palms

Ocho Rios Getaway Villa at The Palms

4 out of 5
Save 100% on your flight
Price was ₩2,764,875, price is now ₩1,492,422 per person
₩1,492,422
per person
Apr 26 - May 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Montego Bay (MBJ)
9.2/10 Wonderful! (7 reviews)
The villa was clean and well appointed. There was comfortable space for four adults though the lounge became somewhat cramped when the fifth adult arrived. There was a sense of safety and security at all times, which was welcome. Everything worked! Though rather removed from the beach there was easy access nonetheless. Other amenities were a short drive away. The corner deli, Scotchies for jerk delights and the petrol station. The highway and Ocho Rios proper were also easily accessible.

Reviewed on Mar 31, 2019

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
Early morning in Hellshire, Jamaica.

Greater Portmore

While Greater Portmore isn't home to many top sights, Sovereign Village Mall and Fort Clarence Beach are some notable places to visit nearby.

Find hotels in Greater Portmore

Find the Best Middlesex County Vacation Packages

Middlesex County Hotel Deals

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 ₩627,516 per night from Apr 1 to Apr 2
₩627,516
₩627,516 total
Apr 1 - Apr 2
includes taxes & fees
8.4/10 Very Good! (2,277 reviews)
Great place

Reviewed on Dec 10, 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 Tower Isle Saint Mary
9.2/10 Wonderful! (1,002 reviews)
Staff was awesome. Rooms were cleaned daily. Pleasantness of staff made the vacation outstanding. My husband and i have not been tk JA in 8 years. This experience is now going to be a yearly trip for us.

Reviewed on Mar 20, 2026

Get rates
Couples Tower Isle All Inclusive
Franklyn D. Resort & Spa

Franklyn D. Resort & Spa

4 out of 5
201 Runaway Bay Runaway Bay Saint Ann
8.6/10 Excellent! (423 reviews)
This place is a hidden gem!!! Owner and staff were amazing… Highly recommend

Reviewed on Mar 15, 2026

Get rates
Franklyn D. Resort & Spa
See all 2,722 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.

Discover the most popular places to visit in Middlesex County

Caymanas Golf and Country Club

Enjoy a round of golf in Kingston at Caymanas Golf and Country Club. Check out the lively bars or top-notch restaurants in this family-friendly area.

Caymanas Golf and Country Club

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.