Middlesex County Holidays

Photo by Mike Gauthier

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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
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Caribbean Estates

Though Caribbean Estates may not have many top sights, you can venture to the surrounding area to see attractions like Sovereign Village Mall and Hellshire Beach.

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Top hotels in Middlesex County

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! (1,001 reviews)
Beyond amazing. Staff were wonderful. Rooms a bit dated but very clean. Food was incredible. Coffee at the Coffee bar is literally to die for. Overall I understand why everyone we met there had been coming back year after year

Reviewed on 17 Dec, 2025

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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
8.2/10 Very Good! (2,507 reviews)
Great place

Reviewed on 10 Dec, 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! (1,000 reviews)
Excellent stay, highly recommended. Hope to return soon 😍

Reviewed on 17 Mar, 2025

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Jewel Paradise Cove Adult Beach Resort & Spa – All Inclusive
See all 2,678 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.

Popular places to visit

Mystic Mountain showing a bay or harbour and a coastal town

Mystic Mountain

4/5(5 reviews)

This popular and exhilarating attraction allows you to experience Jamaica's beautiful rainforest at top speed.

Mystic Mountain
Hellshire Beach

Hellshire Beach

2/5(5 reviews)

Why not spend a care-free afternoon at Hellshire Beach during your travels in Hellshire?

Hellshire Beach

Our Lady of Perpetual Help Roman Catholic Church

Our Lady of Perpetual Help Roman Catholic Church is just one of the places to see in St. Ann's Bay, so why not enjoy the other things to explore during your travels? Wander the beautiful beaches or discover the beautiful waterfalls in this romantic area.

Our Lady of Perpetual Help Roman Catholic Church

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 travellers 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 travelling 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 holiday 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 travelling 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.