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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 travelers. 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.

The Latest Middlesex County vacation packages

Price found within the past 48 hours. Click for updated prices.

Silver Creek Resort

$608

per person

Apr 23 - Apr 30

found 1 day ago

Roundtrip flight included

Boston (BOS) 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

$1,331

per person

May 15 - May 19

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Montego Bay (MBJ)

9/10 Wonderful! (1,010 reviews)

We always enjoy our stay at Sunset at the Palms. The staff are always friendly and quick to accommodate your every need. Parts of the resort could use upgrades. The gym really needs an air conditioner that works. The night entertainment, specifically the piano bar, would benefit from a little more variety and offer different musicians an opportunity to sing.

Reviewed on Mar 22, 2026

Ocho Rios Villa at the Palms V

$1,139

per person

Apr 25 - May 2

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)

No reviews

Ocho Rios Villa at Coolshade X

Save 100% on your flight

$1,149

per person

May 26 - Jun 2

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Montego Bay (MBJ)

9.6/10 Exceptional! (5 reviews)

Ocho Rios Ocean View Villa at The Palms

Save 100% on your flight

$1,099

per person

May 26 - Jun 2

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Montego Bay (MBJ)

8.6/10 Excellent! (9 reviews)

Clean, great customer service. Most importantly we felt safe. Would definitely stay again and again!!

Reviewed on Oct 10, 2024

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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

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.

Discover the most popular places to visit in Middlesex County

Dunn's River Falls

4.5/5(622 reviews)

The natural mineral pools under these beautiful terracing waterfalls are a refreshing treat after a hike through this tropical paradise.

Mystic Mountain

4.5/5(190 reviews)

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

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

Runaway Bay Beach

4/5(519 reviews)

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.

Middlesex County Hotel Deals

Bahia Principe Luxury Runaway Bay - Adults Only - All Inclusive

Salt Coppers Runaway Bay Saint Ann

$417 nightly

$417 total

Apr 1 - Apr 2

Total with taxes and fees

8.4/10 Very Good! (2,277 reviews)

Great place

Reviewed on Dec 10, 2025

Couples Tower Isle All Inclusive

Tower Isle Tower Isle Saint Mary

9.2/10 Wonderful! (1,003 reviews)

The amenity was a little outdated but the good quality food made up for it.

Reviewed on Mar 23, 2026

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Bahia Principe Grand Jamaica - All Inclusive

Salt Coppers Villa Runaway Bay Saint Ann

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See all 2,724 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.