Middlesex Vacation Packages

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Your Middlesex Vacation

The adventure-filled city of Middlesex is calling your name. Uncover both its hidden gems and highlights with a Middlesex vacation 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 traveling. Explore the multitude of options on Expedia today and put your Middlesex vacation plans into gear!

Top Middlesex Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Ocho Rios Villa at The Palms

Ocho Rios Villa at The Palms

3 out of 5
per person
Sep 21 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Montego Bay (MBJ)
10/10 Exceptional! (2 reviews)
Princess Grand Jamaica Resort - All Inclusive

Princess Grand Jamaica Resort - All Inclusive

4.5 out of 5
per person
Oct 6 - Oct 13
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Montego Bay (MBJ)
9/10 Wonderful! (260 reviews)
The staff needs to be more friendly; sometimes they are too stressed and not happy. The hotel is great, and I hope it continues to be like that over time.

Reviewed on Aug. 2, 2025

Alamanda Cottage at Serenity

Alamanda Cottage at Serenity

3 out of 5
Ironshore
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Montego Bay (MBJ)
No 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
Sep 24 - Sep 29
found 10 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Montego Bay (MBJ)
10/10 Exceptional! (2 reviews)
Excellent Resort, especially all the excellence club amenities

Reviewed on May 1, 2025

Retreat Plantation House

Retreat Plantation House

3 out of 5
per person
Sep 7 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Montego Bay (MBJ)
10/10 Exceptional! (1 review)

Ready to book your vacation to Middlesex?

 

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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
The price is CA $542 per night from Sep 3 to Sep 4
CA $542
CA $542 total
Sep 3 - Sep 4
includes taxes & fees
8.6/10 Excellent! (425 reviews)
"The swim up pool and spacious room was spectacular. The food layout in the buffet was very big and had many choices to choose from and the food was tasty. The many restaurants and pool options made our stay very comfortable even though the hotel was busy . I also appreciated many lounge chairs provided ..."

Reviewed on Aug. 1, 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
The price is CA $552 per night from Sep 1 to Sep 2
CA $552
CA $552 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (294 reviews)
"Comparable to most other all inclusives on the island but on the pricier end."

Reviewed on Aug. 2, 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
Fully refundableReserve now, pay when you stay
The price is CA $411 per night from Sep 1 to Sep 2
CA $411
CA $479 total
Sep 1 - Sep 2
includes taxes & fees
9.4/10 Exceptional! (1,999 reviews)
"A repeat favorite pf mine .."

Reviewed on Jul. 31, 2025

S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel
See all 1,466 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.
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Frequently asked questions

How much does a Middlesex vacation package cost?
You'll find cheap prices from CA $1,646 on Expedia for your Middlesex getaway. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Middlesex costs.
What are the cheapest months to go to Middlesex?
January, February and September are great times to search for cheap Middlesex vacation packages. Travelling in quieter months means you can generally find better prices on flights and accommodations.
How many days is enough for Middlesex?
The ideal length of your Middlesex vacation depends on what you'd like to do and see. Typically, a few days to a week will give you time to go to all the major attractions and explore some hidden gems along the way.
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 adventure for midweek, or browse for Middlesex package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Middlesex vacation as a package?
You can enjoy significant savings on your Middlesex break by booking a personalized vacation package. Check the "Package" heading, then select your travel dates and destination to browse some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Middlesex?
Land incredible discounts by reserving your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Middlesex escape.
How to plan a trip to Middlesex?

  1. Pick your travel dates: What you'd like to do in Middlesex and your preferred season can help you decide when to get away.
  2. Calculate your budget: Make sure you have enough money to cover everything from transportation and food to activities and flights. Your hotel will probably be the largest expense during your trip to Middlesex.
  3. Decide how long to go away for: Now that you're more familiar with Middlesex, you can work out the ideal length of your break. Put together a draft plan and give yourself enough time to cover everything you want to see.
  4. Combine your accommodations and airfare: Once you've settled on your travel dates and duration, lock in the perfect Middlesex vacation package for you.

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