Title: Middlesex Vacation Packages & Trips 2026 from CA $1,362 | Expedia.ca [Hotels in Middlesex](https://expedia.ca/Middlesex-Hotels.d553248635975854330.Travel-Guide-Hotels)[Vacation Rentals in Middlesex](https://expedia.ca/Middlesex-Vacation-Rentals.d553248635975854330.Travel-Guide-VacationRentals)[Middlesex Car Rentals](https://expedia.ca/Car-Rentals-In-Middlesex.d553248635975854330.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Middlesex Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### 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](https://www.expedia.ca/Hanover-Museum-Lucea.d553248621533157929.Vacation-Attraction) and [Headland](https://www.expedia.ca/Headland-Lucea.d553248621533157930.Vacation-Attraction). 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 Beach Apt at Sandcastles](https://images.trvl-media.com/lodging/30000000/29850000/29848300/29848230/2ccc8203_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ocho Rios Beach Apt at Sandcastles CA $1,362 per person Jun 3 - Jun 10 found 13 hours ago Roundtrip non-stop flight included Hamilton (YHM) to Montego Bay (MBJ) No reviews ![Sunset at the Palms Resort - Adults Only - All Inclusive](https://images.trvl-media.com/lodging/2000000/1100000/1095800/1095763/459f7c00_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sunset at the Palms Resort - Adults Only - All Inclusive CA $2,261 per person Jun 23 - Jun 30 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Montego Bay (MBJ) 9/10 Wonderful! (1,010 reviews) The staff are amazing! Rooms are clean. Food never disappoints. The gym could use functioning cooling system that works. The hot tub was broken so that was disappointing. The property itself could use a little TLC, buildings, gardens etc. Reviewed on Mar 27, 2026 ![Ocho Rios Villa at the Palms V](https://images.trvl-media.com/lodging/22000000/21400000/21397700/21397611/84003fa1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ocho Rios Villa at the Palms V CA $1,994 per person May 2 - May 9 found 4 hours ago Roundtrip flight included Toronto (YTO) to Montego Bay (MBJ) No reviews ![Ocho Rios Treasure Villa at Coolshade XII](https://images.trvl-media.com/lodging/30000000/29850000/29848300/29848229/94242015_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ocho Rios Treasure Villa at Coolshade XII CA $1,874 per person May 2 - May 9 found 4 hours ago Roundtrip flight included Toronto (YTO) to Montego Bay (MBJ) No reviews ## Ready to book your vacation to Middlesex? Choose your dates ## Middlesex Hotel Deals ![Princess Grand Jamaica Resort - All Inclusive](https://images.trvl-media.com/lodging/97000000/96230000/96229100/96229077/0f4720fb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Princess Grand Jamaica Resort - All Inclusive Industry Cove Green Island Hanover CA $690 CA $690 total Apr 15 - Apr 16 includes taxes & fees 8.8/10 Excellent! (785 reviews) Couldn't have been more happy with our decision to come to the Princess Grand Jamaica. My wife and I traveled with our 2 children aged 6 and 11 and there were plenty of things to do on the property for kids. The dining options were hit or miss but overall there is something for everyone. The pools ... Reviewed on Mar 31, 2026 [](https://expedia.ca/Hotel-Search?startDate=15%2F04%2F2026&endDate=16%2F04%2F2026&selected=96229077&PinnedHotelID=96229077&HadPinnedHotel=true®ionId=553248635975854330) ![Deja Resort All Inclusive](https://images.trvl-media.com/lodging/1000000/560000/554800/554709/6b730830_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Deja Resort All Inclusive 92 Gloucester Avenue Montego Bay Saint James CA $268 CA $316 total Apr 22 - Apr 23 includes taxes & fees 8/10 Very Good! (1,664 reviews) We thoroughly enjoyed our stay at the Deja Resort. Staff was very friendly. Good food and amenities. Nightly entertainment. We loved that we were right across the street from the beach. The beach was sooo beautiful. Bed was comfy. I can go on and on about our love for this resort. Will definitely ... Reviewed on Mar 31, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F04%2F2026&endDate=23%2F04%2F2026&selected=554709&PinnedHotelID=554709&HadPinnedHotel=true®ionId=553248635975854330) ![Princess Senses The Mangrove Resort - Adults Only ](https://images.trvl-media.com/lodging/97000000/96230000/96229200/96229123/01c018b6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Princess Senses The Mangrove Resort - Adults Only Industry Cove Green Island Hanover CA $1,036 CA $1,036 total Apr 14 - Apr 15 includes taxes & fees 9.2/10 Wonderful! (570 reviews) Horrible customer service and communication! Reviewed on Mar 31, 2026 [](https://expedia.ca/Hotel-Search?startDate=14%2F04%2F2026&endDate=15%2F04%2F2026&selected=96229123&PinnedHotelID=96229123&HadPinnedHotel=true®ionId=553248635975854330) [See all 1,542 properties in Middlesex](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=02%2F04%2F2026&endDate=03%2F04%2F2026®ionId=553248635975854330) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## 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. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app