Middlesex Vacations from ￥194,623
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The Latest Middlesex Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Ocean Coral Spring - All Inclusive
Save 100% on your flight
Price was ￥381,574, price is now ￥224,798 per person
￥224,798
per person
Jun 24 - Jun 28
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Montego Bay (MBJ)
8.4/10 Very Good! (4,051 reviews)
Great week with family! Clean resort! Food was great!
Reviewed on Apr 21, 2026
Grand Palladium Jamaica Resort & Spa All Inclusive
Save 100% on your flight
Price was ￥437,794, price is now ￥260,542 per person
￥260,542
per person
Jun 24 - Jun 28
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Montego Bay (MBJ)
8/10 Very Good! (1,574 reviews)
Infinity pool was clean and well maintained. The staff were very friendly. And the food was really good.
Reviewed on Apr 19, 2026
Grand Palladium Lady Hamilton Resort & Spa All Inclusive
Save 100% on your flight
Price was ￥427,296, price is now ￥257,068 per person
￥257,068
per person
Jun 24 - Jun 28
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Montego Bay (MBJ)
8/10 Very Good! (1,411 reviews)
The resort was wonderful. The rooms were kept clean and very spacious. Breakfast was delicious, and the staff was very helpful and kind. Did not have a bad experience and will def do again. There were also little concierge stands by the villas downstairs for anyone who wanted restaurant reservations. Many restaurants to choose from, our fav was the Jamaican restaurant. Jordain the waiter, was so kind and helpful to us. I highly recommend The Grand Palladium. We stayed on the Lady Hamilton Side.
Reviewed on Apr 20, 2026
Hotel Riu Montego Bay - Adults Only - All Inclusive
Save 100% on your flight
Price was ￥428,640, price is now ￥258,030 per person
￥258,030
per person
Jun 24 - Jun 28
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Montego Bay (MBJ)
8.6/10 Excellent! (5,218 reviews)
Definitely was worth it!
Reviewed on Apr 21, 2026
Find the Best Middlesex Vacation Packages
Middlesex Hotel Deals
Princess Grand Jamaica Resort - All Inclusive
Industry Cove Green Island Hanover
The price is ￥72,249 per night from May 10 to May 11
￥72,249
￥72,249 total
May 10 - May 11
includes taxes & fees
8.8/10 Excellent! (905 reviews)
Very clean hotel, food is amazing so I’d definitely recommend!
Reviewed on Apr 21, 2026
Princess Senses The Mangrove Resort - Adults Only
Industry Cove Green Island Hanover
The price is ￥95,098 per night from May 18 to May 19
￥95,098
￥95,098 total
May 18 - May 19
includes taxes & fees
9.2/10 Wonderful! (621 reviews)
I absolutely loved this resort. The buffet breakfast was amazing and the staff was so friendly. The only thing that I didn’t like was that it was always so hot in our room but other than that, our stay was amazing! Can’t wait to go back!
Reviewed on Apr 21, 2026
Deja Resort All Inclusive
92 Gloucester Avenue Montego Bay Saint James
The price is ￥31,128 per night from May 5 to May 6
￥31,128
￥36,738 total
May 5 - May 6
includes taxes & fees
8/10 Very Good! (1,712 reviews)
Breakfast menu wsa fresh, my room overlooked the ocean
Reviewed on Apr 20, 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
