Middlesex Holidays from £1,311

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Your Middlesex Holiday

The adventure-filled city of Middlesex is calling your name. Uncover both its hidden gems and highlights with a Middlesex holiday package that's tailored to you. There's loads to see and do during a trip to Middlesex, including Hanover Museum and Headland. Stop daydreaming and start travelling. Explore the multitude of options on Expedia today and put your Middlesex holiday plans into gear!

The Latest Middlesex Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Ocho Rios Cinnamon Villas

Ocho Rios Cinnamon Villas

3 out of 5
River Oaks
per person
23 Aug - 30 Aug
found 1 day ago
Return flight included
London (LHR) to Montego Bay (MBJ)
10/10 Exceptional! (3 reviews)
The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive

The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive

5 out of 5
per person
23 Aug - 30 Aug
found 1 day ago
Return flight included
London (LHR) to Montego Bay (MBJ)
10/10 Exceptional! (2 reviews)
Excellent Resort, especially all the excellence club amenities

Reviewed on 1 May 2025

Breathless Montego Bay - Adults Only - All Inclusive

Breathless Montego Bay - Adults Only - All Inclusive

5 out of 5
per person
25 Aug - 2 Sept
found 2 hours ago
Return direct flight included
London (LON) to Montego Bay (MBJ)
8.4/10 Very Good! (700 reviews)
Butlers need more interactions with their guests

Reviewed on 21 Jun 2025

Avant Family Villa

Avant Family Villa

3.5 out of 5
per person
23 Aug - 30 Aug
found 1 day ago
Return flight included
London (LHR) to Montego Bay (MBJ)
No reviews
Beautiful property with very responsive and helpful hosts

Reviewed on 21 Jun 2025

Princess Senses The Mangrove Resort - Adults Only

Princess Senses The Mangrove Resort - Adults Only

4 out of 5
per person
31 Jul - 7 Aug
found 18 hours ago
Return direct flight included
London (LGW) to Montego Bay (MBJ)
9.2/10 Wonderful! (200 reviews)
My husband and I were celebrating our 19th anniversary at Princess Senses Mangrove and it did not disappoint. The beach, the room, the property, the food, the drinks.....Excellent!! What was even better than all of this was the amazing staff. From start to finish, the staff truly makes this place. Everyone was so nice and friendly and extremely helpful. Just to name a few...Craig at the front desk during check in, Andrew who greeted us when we first arrived, Sherricka and Neresha at the Food Market was amazing. Both professional and always very friendly. Rayjay serving up delicious drinks.. Allll the shuttle drivers!... all the way to the operators on the phone. Loved it. Had the pleasure of speaking to Enrico the Managing Director who took the time to stop and talk with us so warmly. We ourselves own and run a vacation rental and highly value good customer service, a clean comfortable space and creating a wonderful memory. We appreciate when we can go on vacation and experience what we provide and it exceeds our expectations. Everything at Princess Senses Mangrove was excellent. Would highly recommend this hotel. Whether its just for a few days or for a week like us, it will be worth it.

Reviewed on 23 Jun 2025

Princess Grand Jamaica Resort - All Inclusive

Princess Grand Jamaica Resort - All Inclusive

4.5 out of 5
per person
31 Jul - 7 Aug
found 18 hours ago
Return direct flight included
London (LGW) to Montego Bay (MBJ)
8.8/10 Excellent! (200 reviews)
I loved the resort but didn’t like the small part of the beach

Reviewed on 23 Jun 2025

Middlesex Essential Information

Language
English
Currency
Jamaican dollars
Closest Airport
Sir Donald Sangster Intl. Airport (MBJ)
Max Temp Winter
27ºC
Max Temp Summer
29ºC
Top Sights
Half Moon Beach, Tryall Golf Club and Hanover Museum

Our pick of the best Middlesex Hotel Deals

Princess Grand Jamaica Resort - All Inclusive
Princess Grand Jamaica Resort - All Inclusive
4.5 out of 5
Industry Cove, Green Island, Hanover
Stay at this 4.5-star luxury resort in Green Island. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Half Moon Beach and Samuel's Bay ...
8.8/10 Excellent! (210 reviews)
"I like ambiance of the hotel,very beautiful, i had the swim out pool suite ❗️5stars❗️The beach wasnt inviting and they need to do something about the flies in buffet area"

Reviewed on 22 Jun 2025

Princess Grand Jamaica Resort - All Inclusive
Princess Senses The Mangrove Resort - Adults Only
Princess Senses The Mangrove Resort - Adults Only
4 out of 5
Industry Cove, Green Island, Hanover
Stay at this 4-star beach resort in Green Island. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Half Moon Beach and Samuel's Bay National ...
9.2/10 Wonderful! (207 reviews)
"Great place"

Reviewed on 21 Jun 2025

Princess Senses The Mangrove Resort - Adults Only
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
Stay at this 4-star beach resort in Montego Bay. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the pool and the bar in their reviews. ...
9.4/10 Exceptional! (1,943 reviews)
"Our stay at the S Hotel was exceptional!!!! The property is stunning, with a relaxed atmosphere, incredibly friendly staff, spacious rooms with comfortable beds, gorgeous beach and a wide variety of delicious foods!! The location is also perfect; less than 10 minutes from Sangster Int'l Airport. ..."

Reviewed on 22 Jun 2025

S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel
See all 1,481 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 Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Middlesex travel package cost?
Get set to book, because a getaway to Middlesex starts from only £1,311. When you bundle your flights, hotels and car rentals into a travel package, you'll walk away with the best deals.
If I'm not able to travel, can I cancel my Middlesex travel package?
Because we understand life can be unpredictable, the answer is yes. For more information, visit our Customer Service Portal. But generally speaking, if you've made your booking in the last 24 hours, you may be able to change or cancel it for free. Your hotel, airline or car rental company may impose a fee if you made your booking a while ago.
How do I get a cheap travel package to Middlesex?
Bundling your hotel and flight with Expedia won't just save valuable time --- it'll save you cash too. A Middlesex holiday package makes it a breeze to arrange the ideal trip. With more than 550 airlines around the world to choose from, finding convenient flights that fit your busy schedule won't be difficult. Not only that, we have over 1,000,000 properties globally to select from. Now that's choice! No matter who you are, Expedia puts the world within your reach.
Does Expedia offer Book Now, Pay Later Middlesex holidays?
Expedia has joined forces with online lender Klarna to make your next break a little easier on the wallet. Paying in instalments means you can spread the costs of your next big adventure, leaving you with more money to play with while you're away. Klarna has several payment plans to choose from, so you're sure to find something that falls within your budget. Check out these flexible payment options:
  • Pay monthly holidays: If paying small amounts each month is what works best for you, Klarna can help. Paying in convenient monthly instalments will make that dream getaway possible.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay off your trip across multiple transactions.
  • Low deposit holidays: If paying a small percentage of your trip (rather than all of it upfront) makes it easier to hit that "book now" button, choose a low deposit holiday payment plan from Klarna.

Where should I stay in Middlesex?
With popular attractions such as Dolphin Cove Negril and Hanover Museum in this neighbourhood, look for a hotel situated near either of them. Headland is another Middlesex hot spot that people flock to.
What are the top hotels in Middlesex?
If it's your first time staying in Middlesex, make a reservation at Grand Palladium Jamaica Resort And Spa or Royalton Negril, An Autograph Collection All-Inclusive Resort. Both will make you feel at home and are favourites with many travellers.
How far in advance should I book my Middlesex holiday?
Savvy travellers book early. Air carriers typically release flight tickets nearly 12 months ahead of departure, and this is when you can pick up some of the lowest prices. Boss just told you to take your holiday time next week? Don't fret. Expedia are never short on fantastic deals to send you off on the getaway of your dreams, at an affordable price.
What does an Expedia Middlesex travel package include?
Hotels, flights and a shiny set of wheels for all your road trip adventures. Simply select your favourite bundle and get access to incredible deals. Once you've made your booking, add on some tours and experiences and watch your savings grow. When it comes to creating your Middlesex break, you're in control!
What should I know before booking a Middlesex travel package?
Discover deals that suit your budget with an Expedia package. Flights, hotels, rental cars --- we have everything you need to plan your break. You'll save a packet just by bundling your bookings. Whether you're taking off on a winter adventure or kicking back on a warm beach, your ideal holiday is just a few clicks away.
Can I choose my airline with a Middlesex Expedia travel package?
Definitely. Expedia has over 550 airline partners to choose from worldwide. With so much choice, finding the ideal carrier to fly you to Middlesex will be a snap.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.