Middlesex County Vacation Packages 2026 from $1,091

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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.

Ocho Rios Villa at the Palms V

Save 100% on your flight

$1,091

per person

Sep 25 - Oct 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Montego Bay (MBJ)

No reviews

Sunset at the Palms Resort - Adults Only - All Inclusive

$1,098

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Montego Bay (MBJ)

9.2/10 Wonderful! (1,007 reviews)

Ocean Eden Bay - Adults Only - All inclusive

$1,231

per person

Oct 27 - Nov 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Montego Bay (MBJ)

8.4/10 Very Good! (3,910 reviews)

Ocho Rios Villa at The Palms

$1,253

per person

Sep 24 - Oct 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Montego Bay (MBJ)

10/10 Exceptional! (2 reviews)

All staff were professional, courteous and friendly. They all went out of their way to grant your requests. The ambience is very nice. The electrical outlets on the patio didn't always work. Had to be creative in getting plugs to stay in. They also need to upgrade from 110v to 220v. Just kidding, but they should have something for travelers from Europe. Internet service was pretty good. Everyone in my group were pleased and would return. The tour setup for us by the manager was fun!!!! Good people, fantastic accommodations. Recommended...

Reviewed on May 8, 2019

Ocho Rios Villa at Coolshade X

Save 100% on your flight

$1,227

per person

Sep 24 - Oct 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Montego Bay (MBJ)

9.6/10 Exceptional! (5 reviews)

Very impressive and well kept property in a quiet gated community. We did not have a car, so organizing transportation was challenging, but the grocery store is only a 20 minute walk away (for those who enjoy walking). I did not rate it 5 stars because it was difficult to communicate with the property managers in advance. They finally contacted me the day before check in, and it was not obvious that I needed to pay a balance and deposit in cash US dollars upon arrival (most places accept credit card). We worked it out, but it did add a layer of unnecessary stress - they could have simply sent a message with the balance and instructions after booking so that travellers could be better prepared.

Reviewed on Apr 11, 2023

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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

A coastal town with houses near the beach, a pier, and mountains in the background.

Greater Portmore

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

A pier extending into a turquoise sea, surrounded by lush greenery and buildings with red roofs.

Caribbean Estates

While there might not be top attractions in Caribbean Estates, you can explore the larger area and discover places like Hellshire Beach and Caymanas Golf and Country Club.

A beach with clear turquoise water, a row of tiki statues, and a white house with a balcony in the background.

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.

Great Pond

If you're looking for some top things to see and do in Great Pond and surrounding area, you can visit Mahogany Beach and Ocho Rios Clock Tower.

Aerial Bird's eye view of Jamaica parish of Saint Catherine or St. Catherine

Bridgeport

Though Bridgeport might not have many top sights, you can venture to the surrounding area to see attractions like Hellshire Beach and Fort Clarence Beach.

Stay near popular Middlesex County attractions

A waterfall cascading over rocks in a forested area with a 'No Carving of Rocks' sign.

Dunn's River Falls

9.2/10 (3,777 reviews)

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

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A water slide with a pool at the bottom, surrounded by lush greenery and a view of a coastal town.

Mystic Mountain

8.8/10 (1,373 reviews)

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

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A beach with clear turquoise water, a thatched-roof hut, and a large resort building in the background.

Runaway Bay Beach

8.6/10 (2,822 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 romantic area.

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A waterfall cascading over rocks into a turquoise pool surrounded by dense forest.

Cool Blue Hole

9.4/10 (357 reviews)

Explore the great outdoors at Cool Blue Hole and enjoy the beautiful waterfalls during your trip to Ocho Rios. Stroll along the seaside or experience the entertainment choices in this romantic area.

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A beach with a wooden structure and a stone wall.

Hellshire Beach

8.2/10 (148 reviews)

Why not spend a carefree afternoon at Hellshire Beach during your travels in Hellshire?

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A beach with a lifeguard tower, thatched umbrellas, and a calm sea.

Ocean View Beach

8.6/10 (1,254 reviews)

Why not spend a carefree afternoon at Ocean View Beach during your travels in Runaway Bay? Discover the top-notch restaurants and entertainment choices in this romantic area.

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Mahogany Beach

8.4/10 (382 reviews)

Why not spend a carefree afternoon at Mahogany Beach during your travels in Ocho Rios? Wander the riverfront or discover the beautiful waterfalls in this romantic area.

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Ocho Rios Fort

8.4/10 (522 reviews)

Learn about the local history of Ocho Rios with a stop at Ocho Rios Fort. Stroll along the riverfront or discover the beautiful waterfalls in this romantic area.

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Middlesex County Hotel Deals

Bahia Principe Escape Runaway Bay - Hyatt Inclusive Collection - Adults Only - All Inclusive

Salt Coppers Runaway Bay Saint Ann

$303 nightly

$303 total

Sep 22 - Sep 23

Total with taxes and fees

8.4/10 Very Good! (2,488 reviews)

"Property should have broader selection of Jamaican food otherwise experience was pleasant"

Reviewed on Aug 23, 2026

Couples Tower Isle All Inclusive

Tower Isle Tower Isle Saint Mary

9.2/10 Wonderful! (1,008 reviews)

"Nudity, nothing"

Reviewed on Aug 21, 2026

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Franklyn D. Resort & Spa

201 Runaway Bay Runaway Bay Saint Ann

8.6/10 Excellent! (467 reviews)

"The view was spectacular. Watching the waves from my room was breathtaking."

Reviewed on Aug 21, 2026

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See all 2,866 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.