Title: Middlesex Vacation Packages & Trips 2026 from CA $859 | 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. ![Silver Creek Resort](https://images.trvl-media.com/lodging/12000000/11450000/11444200/11444133/a6e5389d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Silver Creek Resort CA $859 per person Jun 13 - Jun 20 found 1 day ago Roundtrip flight included Toronto (YTO) to Montego Bay (MBJ) 7/10 Good! (51 reviews) The only concern we had was that there is no restaurants within walking distance, Reviewed on May 20, 2024 ![Ocho Rios Villa at the Palms VII](https://images.trvl-media.com/lodging/23000000/22970000/22964500/22964448/1a5e1a7a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ocho Rios Villa at the Palms VII CA $1,828 per person Jun 4 - Jun 11 found 1 day ago Roundtrip flight included Toronto (YYZ) to Montego Bay (MBJ) No reviews ![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 1 day 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 1 day ago Roundtrip flight included Toronto (YTO) to Montego Bay (MBJ) No reviews ![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 1 day ago Roundtrip non-stop flight included Hamilton (YHM) 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 $688 CA $688 total Apr 22 - Apr 23 includes taxes & fees 8.8/10 Excellent! (794 reviews) Girls trip with my sixteen year old daughter for the beach/pool. Large hotel, our room was on the 2nd floor of building six on the beachside. Room was very clean and well maintained. We felt that this side must be much quieter than rooms facing the water park and pool as the moonlight theatre entertainment ... Reviewed on Apr 2, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F04%2F2026&endDate=23%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 Fully refundableReserve now, pay when you stay CA $273 CA $323 total Apr 29 - Apr 30 includes taxes & fees 8/10 Very Good! (1,662 reviews) The hotel is overall an older hotel. The staff and management try their best, but it is old. While the hotel is dated, it was clean. The staff is very friendly. The food is all right. We were here March 2026 during spring break time. The hotel was relatively busy. The location is central to Montego ... Reviewed on Apr 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=29%2F04%2F2026&endDate=30%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 $1,034 CA $1,034 total Apr 22 - Apr 23 includes taxes & fees 9.2/10 Wonderful! (573 reviews) Excellent stay at the Princess. My only recommendation is to have a hot tub or two. Having a pool with jet but water is cold defeats the purpose. Additionally charging for room service does not allow for the adult only feeling. Reviewed on Apr 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F04%2F2026&endDate=23%2F04%2F2026&selected=96229123&PinnedHotelID=96229123&HadPinnedHotel=true®ionId=553248635975854330) [See all 1,543 properties in Middlesex](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=03%2F04%2F2026&endDate=04%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