Middlesex Holidays from £1,448

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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
per person
12 Oct - 18 Oct
found 1 day ago
Return flight included
Birmingham (BHX) to Montego Bay (MBJ)
8.2/10 Very Good! (3,765 reviews)
Staff was very courteous n friendly beautiful design .

Reviewed on 11 Aug 2025

The Signature Level At Grand Palladium Lady Hamilton Resort & Spa

The Signature Level At Grand Palladium Lady Hamilton Resort & Spa

5 out of 5
Save 100% on your flight
per person
15 Oct - 22 Oct
found 1 day ago
Return direct flight included
London (LHR) to Montego Bay (MBJ)
8.6/10 Excellent! (90 reviews)
Me and my hubby enjoyed our first trip out the country to Jamaica and we will never forget it! The staff were truly amazing; they were like family to us. It was very relaxing, but the Bob Marley performance, all white party, and pool party they had while we were vacationing was so much fun! The food was delicious, the hibachi was so much fun as well! We met so many people from around the world and the vibes were definitely vibing! The excursions were breathtaking, fun, and worth it! Lastly, me and my hubby were pleasantly surprised by our hotel and the balcony view it was absolutely beautiful and amazing to wake up to. Overall I give this vacation and stay a 10/10 💗

Reviewed on 4 Aug 2025

Princess Senses The Mangrove Resort - Adults Only

Princess Senses The Mangrove Resort - Adults Only

4 out of 5
per person
12 Oct - 18 Oct
found 1 day ago
Return flight included
Birmingham (BHX) to Montego Bay (MBJ)
9.2/10 Wonderful! (300 reviews)
My experience was superb, the butler service was amazing, the food was amazing! I will definitely be revisiting this property. 5/5 Highly recommended property.

Reviewed on 11 Aug 2025

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
12 Oct - 18 Oct
found 1 day ago
Return flight included
Birmingham (BHX) to Montego Bay (MBJ)
10/10 Exceptional! (2 reviews)
Excellent Resort, especially all the excellence club amenities

Reviewed on 1 May 2025

Casa Marina Montego Bay at Seawind

Casa Marina Montego Bay at Seawind

3 out of 5
Save 100% on your flight
per person
17 Sept - 23 Sept
found 16 hours ago
Return flight included
Birmingham (BHX) to Montego Bay (MBJ)
8.4/10 Very Good! (5 reviews)

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 £324 per night from 26 Aug to 27 Aug
£324
26 Aug - 27 Aug
includes taxes & fees
8.6/10 Excellent! (469 reviews)
"Awesome!"

Reviewed on 8 Aug 2025

Princess Grand Jamaica 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
Fully refundableReserve now, pay when you stay
The price is £249 per night from 10 Sept to 11 Sept
£249
10 Sept - 11 Sept
includes taxes & fees
9.4/10 Exceptional! (2,016 reviews)
"A great place to stay for a low-key vacation with your spouse and some friends. Very close to other activities’ locations and easy transportation. The staff are also super helpful."

Reviewed on 9 Aug 2025

S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel
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 £316 per night from 10 Sept to 11 Sept
£316
10 Sept - 11 Sept
includes taxes & fees
9/10 Wonderful! (310 reviews)
"Very beautiful resort. However, food and entertainment options are subpar at best. I was unfortunately disappointed. Nadia in the spa is THE BEST! If you stay here, get the platinum club, that’s where the food is good."

Reviewed on 8 Aug 2025

Princess Senses The Mangrove Resort - Adults Only
See all 1,482 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
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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 £1,448. 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.