Middlesex Holidays

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Top Flight + Hotel Deals in Middlesex

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
28 Sept - 4 Oct
found 12 hours ago
Return flight included
New York (JFK) to Montego Bay (MBJ)
8.2/10 Very Good! (3,736 reviews)
I was welcomed by Stacia at the privilege lounge who was very attentive and helpful. She assured me my stay was going to be a wonderful experience and sure enough it was!

Reviewed on 6 Aug 2025

Princess Senses The Mangrove Resort - Adults Only

Princess Senses The Mangrove Resort - Adults Only

4 out of 5
per person
13 Oct - 20 Oct
found 1 hour ago
Return direct flight included
Dublin (DUB) to Montego Bay (MBJ)
9.2/10 Wonderful! (291 reviews)
Everything was good minus our bathroom we had to flush more than one time for our waste to go down but loved everything else other than that . Beautiful property && great staff .

Reviewed on 7 Aug 2025

Princess Grand Jamaica Resort - All Inclusive

Princess Grand Jamaica Resort - All Inclusive

4.5 out of 5
per person
28 Sept - 4 Oct
found 12 hours ago
Return flight included
New York (JFK) to Montego Bay (MBJ)
8.8/10 Excellent! (401 reviews)
It was outstanding.. service, food! Place.. everything, definitely will come back!

Reviewed on 7 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
13 Oct - 20 Oct
found 1 hour ago
Return direct flight included
Dublin (DUB) to Montego Bay (MBJ)
10/10 Exceptional! (2 reviews)
Excellent Resort, especially all the excellence club amenities

Reviewed on 1 May 2025

Hotel Riu Palace Aquarelle - All Inclusive

Hotel Riu Palace Aquarelle - All Inclusive

4 out of 5
Save 100% on your flight
per person
13 Oct - 20 Oct
found 1 hour ago
Return direct flight included
Dublin (DUB) to Montego Bay (MBJ)
8.8/10 Excellent! (1,656 reviews)
Everything was amazing! Food, restaurants and even the buffet. I'm not a huge buffet person but theirs was awesome! Lots of choices. Very clean and the rooms were great! Views of the Ocean and the beach was fantastic! I normally drink only wine but the drinks were super good- love the featured cocktail menu at the bars- we tried them all, and if you go, must get the Bob & Rita Marley! Entertainment was top notch and the dancers are tremendous with a ton of "riz" as the kids call it! This resort won't disappoint. Some feedback or suggestions- rotate the food at Pepe's Place. A lot of resorts in Cancun do this on the pool decks. Maybe an ice cream or gelato station! Offer more than 1 night of Karaoke or a separate area to have several ops for this. Kids love it! Slides were SUPER fun and safe. All I can say is yeah mon! We traveled with 11 of us and we all had an amazing time! Great job Riu Palace Aquarelle!

Reviewed on 6 Aug 2025

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 €415 per night from 20 Aug to 21 Aug
€415
20 Aug - 21 Aug
includes taxes & fees
8.6/10 Excellent! (446 reviews)
"The property is beautiful and well maintained"

Reviewed on 5 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 €341 per night from 3 Sept to 4 Sept
€341
3 Sept - 4 Sept
includes taxes & fees
9.4/10 Exceptional! (2,010 reviews)
"Food options were very limited. the buffet needs to be expanded. The seafood restaurant needs to offer more seafood options and better portion size, and work on there service. The Italian and Jamaican restaurant, they were both very good, great service, portions were good, but a very few options ..."

Reviewed on 5 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 €572 per night from 24 Aug to 25 Aug
€572
24 Aug - 25 Aug
includes taxes & fees
9.2/10 Wonderful! (303 reviews)
"Our Butler Henrique was awesome and did a fabulous job and made our vacation a memorable 1"

Reviewed on 5 Aug 2025

Princess Senses The Mangrove Resort - Adults Only
See all 1,465 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.

Frequently asked questions

How much does a Middlesex holiday package cost?
Offering great value package deals from €909 on Expedia, you'll be thrilled with how little a holiday to Middlesex costs! Our packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Middlesex?
You can generally find lower prices and better availability in January, February and September. Check out our cheap Middlesex holiday packages and you could get some excellent off-season deals.
How many days is enough for Middlesex?
With a well-planned itinerary, you can easily tick off the most popular Middlesex sights in a few days. But if you'd like to explore off the beaten track or go on day trips, think about booking your Middlesex holiday for longer.
How to find the best Middlesex package deals?
Use Expedia's filters to find some fabulous Middlesex package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Middlesex package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your holiday package as early as possible.
Is it cheaper to book a Middlesex holiday as a package?
You can enjoy significant savings on your Middlesex getaway by booking a customised holiday package. Check the "Package" heading, then enter your travel dates and destination to see the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday package to Middlesex?
If you're planning a spur-of-the-moment Middlesex holiday, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Middlesex?

  1. Choose when to go: Check your schedule and get your bags packed. Your preferred time of year and the type of activities on offer will also help you decide when to escape to Middlesex.
  2. Budget wisely: Besides the cost of your hotel, you'll need to factor in other expenses. These include food, flights and transportation. Also, set aside some extra funds for unexpected costs that could arise during your trip to Middlesex.
  3. Decide how long to go for: Now that you're more familiar with Middlesex, you can figure out the perfect length of your holiday. Create a rough plan and give yourself enough time to cover everything you want to see.
  4. Bundle your accommodation and airfare: Once you've settled on your dates and duration, lock in the perfect Middlesex holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.