Middlesex Holidays from £1,315

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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!

Top Middlesex Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Ocean Coral Spring - All Inclusive

Ocean Coral Spring - All Inclusive

5 out of 5
Save 100% on your flight
Price was £2,205, price is now £1,315 per person
£1,315
per person
15 Sept - 20 Sept
found 1 day ago
Return direct flight included
London (LON) to Montego Bay (MBJ)
8.4/10 Very good! (4,136 reviews)
Pros: The food was great. Property was clean and well maintained. Con: check in process was bad. Took my 90 years old grandma for Mother’s Day weekend and ended up sitting in the lobby for hours.

Reviewed on 14 Jul 2026

Sunset at the Palms Resort - Adults Only - All Inclusive

Sunset at the Palms Resort - Adults Only - All Inclusive

4.5 out of 5
Save 100% on your flight
Price was £2,821, price is now £1,535 per person
£1,535
per person
15 Sept - 20 Sept
found 1 day ago
Return direct flight included
London (LON) to Montego Bay (MBJ)
9.2/10 Wonderful! (1,003 reviews)
Had a wonderful time!

Reviewed on 13 Jul 2026

Ocean Eden Bay - Adults Only - All inclusive

Ocean Eden Bay - Adults Only - All inclusive

5 out of 5
Save 100% on your flight
Price was £2,392, price is now £1,379 per person
£1,379
per person
15 Sept - 20 Sept
found 1 day ago
Return direct flight included
London (LON) to Montego Bay (MBJ)
8.4/10 Very good! (3,873 reviews)
Resort is marketed as luxury but it was really just expensive. Beautiful grounds and pool area but the rooms felt and looked refurbished. Customer service was poor in general but especially at the Red Snapper restaurant. Ladies at Captain's buffet were lovely.

Reviewed on 15 Jul 2026

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
Save 100% on your flight
Price was £7,843, price is now £4,622 per person
£4,622
per person
15 Sept - 20 Sept
found 1 day ago
Return direct flight included
London (LON) to Montego Bay (MBJ)
10/10 Exceptional! (2 reviews)
Excellent Resort, especially all the excellence club amenities

Reviewed on 1 May 2025

Princess Grand Jamaica Resort - All Inclusive

Princess Grand Jamaica Resort - All Inclusive

4.5 out of 5
Save 100% on your flight
Price was £3,791, price is now £2,288 per person
£2,288
per person
15 Aug - 22 Aug
found 1 day ago
Return flight included
London (LON) to Montego Bay (MBJ)
9/10 Wonderful! (1,302 reviews)
Staff was courteous and helpful.

Reviewed on 15 Jul 2026

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

Top hotels in Middlesex

Princess Grand Jamaica Resort - All Inclusive

Princess Grand Jamaica Resort - All Inclusive

4.5 out of 5
Industry Cove Green Island Hanover
The price is £410 per night from 10 Aug to 11 Aug
£410
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (1,401 reviews)
"Staff was courteous and helpful."

Reviewed on 15 Jul 2026

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
The price is £456 per night from 12 Aug to 13 Aug
£456
12 Aug - 13 Aug
includes taxes & fees
9.4/10 Exceptional! (834 reviews)
"The hotel was very clean, the staff was attentive, and the food was delicious!"

Reviewed on 15 Jul 2026

Princess Senses The Mangrove Resort - Adults Only
Deja Resort All Inclusive

Deja Resort All Inclusive

3.5 out of 5
92 Gloucester Avenue Montego Bay Saint James
The price is £201 per night from 10 Aug to 11 Aug
£201
10 Aug - 11 Aug
includes taxes & fees
8.2/10 Very good! (1,889 reviews)
"The food was great always ready for the gas clean tasty variety of Jamaican style as well as American style. Lots of flavors. Hotel is super convenient for the beach with free access beautiful pristine water lots of little shopping areas many different restaurants lots of friendly locals. Make sure ..."

Reviewed on 15 Jul 2026

Deja Resort All Inclusive
See all 1,540 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
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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 £1,315. 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.

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. Flight-inclusive packages are ATOL protected.