Middlesex Vacations from $883

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Your Middlesex Vacation

Take the hassle out of organizing your next big adventure with a Middlesex vacation package. Whether you're lured here by its landmarks, food or other highlights, this city offers countless exciting experiences to delve into. When the time comes to get out and explore, be sure to put Hanover Museum and Headland on the to-do list for your trip to Middlesex. Stop daydreaming and start doing. Browse the wide range of options on Expedia today and finally put your Middlesex vacation plans into action!

The Latest Middlesex Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Riu Montego Bay - Adults Only - All Inclusive

Riu Montego Bay - Adults Only - All Inclusive

4 out of 5
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Montego Bay (MBJ)
8.4/10 Very Good! (4,057 reviews)
I enjoyed my stay, the entertainment was dope..the staff were good and respectful. I’ll be comin back. My favorite reserved restaurant was the Sofia Italian restaurant..mainly for their salmon and mussels.

Reviewed on Jun 19, 2024

Sunset at the Palms Resort - Adults Only - All Inclusive

Sunset at the Palms Resort - Adults Only - All Inclusive

4.5 out of 5
per person
Aug 25 - Aug 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Montego Bay (MBJ)
9.2/10 Wonderful! (1,018 reviews)
Exceeded all our expectations! The pictures don’t do it justice, and the staff is absolutely wonderful. Probably the best all inclusive resort we’ve ever experienced. We’ll definitely be back.

Reviewed on Jun 18, 2024

RIU Palace Tropical Bay - All Inclusive

RIU Palace Tropical Bay - All Inclusive

4 out of 5
Save 100% on your flight
per person
Aug 11 - Aug 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Montego Bay (MBJ)
8.6/10 Excellent! (1,004 reviews)
We had a great stay. This is my second time at this property. I love the employees and all of the entertainment. We will be back soon.

Reviewed on Jun 17, 2024

RIU Ocho Rios - All Inclusive

RIU Ocho Rios - All Inclusive

3.5 out of 5
Save 100% on your flight
per person
Aug 7 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Montego Bay (MBJ)
8.2/10 Very Good! (2,782 reviews)
Loved the pools and beach!

Reviewed on Jun 18, 2024

RIU Negril - All Inclusive

RIU Negril - All Inclusive

3.5 out of 5
Save 100% on your flight
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Montego Bay (MBJ)
7.8/10 Good! (1,003 reviews)
Enjoyed RIU Negril. People were great, friendly smiles, and overall nice. I appreciated the Love.

Reviewed on Jun 16, 2024

Middlesex Essential Information

Language
English
Currency
Jamaican dollars
Closest Airport
Sir Donald Sangster Intl. Airport (MBJ)
Top Sights
Half Moon Beach, Tryall Golf Club and Hanover Museum

Middlesex Hotel Deals

SeaGarden Beach Resort - All Inclusive
SeaGarden Beach Resort - All Inclusive
3.5 out of 5
8 Kent Avenue, Montego Bay, Saint James
The price is $215 per night from Jun 24 to Jun 25
$215
$252 total
includes taxes & fees
Jun 24 - Jun 25
7.4/10 Good! (2,231 reviews)
"Personal so profesional and nice Best food ever"

Reviewed on Jun 17, 2024

SeaGarden Beach Resort - All Inclusive
S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel
S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel
4 out of 5
7 Jimmy Cliff Blvd, Montego Bay, Saint James
The price is $548 per night from Jul 4 to Jul 5
$548
$548 total
includes taxes & fees
Jul 4 - Jul 5
9.4/10 Exceptional! (1,675 reviews)
"I will definitely be coming back to this hotel. The staff is so professional and friendly. I also love the fact that the hotel manager walks the property and interact with the guests and encourages you to voice any concerns. The food was amazing the bartenders are very knowledgeable. The beach and ..."

Reviewed on Jun 17, 2024

S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel
Grand Palladium Lady Hamilton Resort & Spa All Inclusive
Grand Palladium Lady Hamilton Resort & Spa All Inclusive
4.5 out of 5
The Point, Lucea, Hanover
7.6/10 Good! (1,168 reviews)
"Grand Palladium is so beautiful and clean. There were a lot of things to do at the resort."

Reviewed on Jun 14, 2024

Get rates
Grand Palladium Lady Hamilton Resort & Spa All Inclusive
See all 1,598 properties in Middlesex
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

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Frequently asked questions

How much does a Middlesex vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Middlesex from just $883. And the more you bundle, the more money you save. The vacation of your dreams has never been so affordable.
How do I get a cheap travel package to Middlesex?
Bundling your flight and hotel with Expedia won’t just save precious time — it’ll save you cash too. A Middlesex vacation package makes it simple to create your dream adventure. With more than 550 airlines all over the world to choose from, finding flights that fit your busy schedule won’t be an issue. In addition to that, we have over 1,000,000 hotel options globally to take your pick of. Now that’s choice! Whatever your budget, Expedia puts more of the world within your reach.
Where should I stay in Middlesex?
With so much to explore in Middlesex, we recommend you lock in a hotel near its attractions. Dolphin Cove Negril, Hanover Museum and Headland are some fascinating ones to add to your itinerary.
How far in advance should I book my Middlesex vacation?
Reserving your tickets early with Expedia means one less thing to worry about. Most carriers display prices up to 12 months in advance. This is generally the cheapest time to book. If circumstances have left you booking late, low prices to Middlesex sometimes occur a few weeks before departure.
What does an Expedia Middlesex travel package include?
With Expedia, you can choose a combination of hotels, car rentals and flights to create your perfect Middlesex travel package. Once you’ve made your booking, you can add on the fun stuff like sightseeing tours and activities. Don’t forget, the more you bundle, the bigger the savings!
What should I know before booking a Middlesex travel package?
Whether it’s relaxation or adventure you’re after, a Middlesex vacation package lets you organize your escape your way. Plus, you’ll get access to great discounts just for combining your hotel with your rental car and flights. The more you bundle, the bigger the savings!
Can I choose my airline with a Middlesex Expedia vacation package?
You sure can. We offer more than 550 partner airlines around the world, so pick the carrier that fits your travel needs.
If I'm not able to travel, can I cancel my Middlesex vacation package?
Don’t worry if you’re rethinking your Middlesex vacation package — it’s possible to cancel or amend your booking. And if you’ve booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur charges from your hotel, airline or car rental company. We totally get that life can sometimes throw a spanner in the works, so look up our Customer Service Portal if that occurs. When you’re ready to make changes, we’ll take care of it.

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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.