Middlesex County Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Mike Gauthier

  • Plan, book, travel with confidence

  • Better together

    Save up to ₩1,660,000 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

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

Find the Best Middlesex County Vacation Packages

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 ₩576,389 per night from Jun 23 to Jun 24
₩576,389
₩576,389 total
Jun 23 - Jun 24
includes taxes & fees
8.4/10 Very Good! (2,364 reviews)
"the room was clean and wonderful. the staffs were great and helpful. the bar liquor could be a bit more upscale. the lighting in the piccasso dining room near the corner tables should be altered so none hit their head including the waiter who has to constantly bend to avoid the fixture."

Reviewed on Jun 21, 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! (1,000 reviews)
"Lush garden. The lobby has plenty seating. Did not enjoy the hotel. I do believed I didnt get the room that I paid for. The air conditioner was first so loud. The man came and bridge it with a piece of wood. We had to turn it off and use the fan. The bathroom had rust on the soap dish holder and ..."

Reviewed on Jun 17, 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! (449 reviews)
"if you have kids ages babies to I would say 12 this would be the ideal place , quaint intimate and gives parents especially SINGLE MOTHERS A break .They have snorkeling that comes with your stay, scuba if you want I think .. access to an amazing beach off the side of the property.. The food is great ..."

Reviewed on Jun 14, 2026

Get rates
Franklyn D. Resort & Spa
See all 2,811 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

5/5(5 reviews)

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

Caymanas Golf and Country Club

Mega Mart

4/5(6 reviews)

During your visit to Mandeville, you can browse for the perfect souvenirs at Mega Mart. Wander the parks and gardens while you're in the area.

Mega Mart

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.