Title: Middlesex Vacation Packages & Trips 2026 from CA $848 | 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/e6055a65_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Silver Creek Resort CA $848 per person Apr 25 - May 2 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) 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 V](https://images.trvl-media.com/lodging/22000000/21400000/21397700/21397611/d97329ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ocho Rios Villa at the Palms V CA $1,632 per person Apr 29 - May 6 found 1 day ago Roundtrip flight included Toronto (YYZ) to Montego Bay (MBJ) No reviews ![Ocho Rios Villa at Coolshade](https://images.trvl-media.com/lodging/17000000/16110000/16104900/16104814/56f2376a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ocho Rios Villa at Coolshade CA $1,175 per person Apr 18 - Apr 24 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Montego Bay (MBJ) 6/10 (18 reviews) The host was wonderful and quite responsive. I will definately stay again and highly recomend. Reviewed on Mar 18, 2023 ![Ocho Rios Tranquility at Coolshade VII](https://images.trvl-media.com/lodging/20000000/19440000/19436600/19436549/fb7d1c8e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ocho Rios Tranquility at Coolshade VII CA $1,331 per person Apr 18 - Apr 24 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Montego Bay (MBJ) No reviews ![Ocho Rios Villa at Coolshade IV](https://images.trvl-media.com/lodging/15000000/14730000/14727900/14727867/3c04274d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ocho Rios Villa at Coolshade IV CA $1,379 per person Apr 18 - Apr 24 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Montego Bay (MBJ) 9.4/10 Exceptional! (10 reviews) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_553248635975854330) ## 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/97000000/96230000/96229100/96229077/179083ab_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Princess Grand Jamaica Resort - All Inclusive Industry Cove Green Island Hanover CA $639 CA $639 total Mar 1 - Mar 2 includes taxes & fees 8.8/10 Excellent! (709 reviews) The property was beautiful with an abundance of pools, restaurants, and entertainment. The staff were incredible and very accommodating! Everyone was very helpful and kind to us and our 9 month old baby. There was a small drainage issue in our shower that caused some flooding. The hotel was very ... Reviewed on Jan 17, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=96229077&PinnedHotelID=96229077&HadPinnedHotel=true®ionId=553248635975854330) ![Princess Senses The Mangrove Resort - Adults Only ](https://images.trvl-media.com/lodging/97000000/96230000/96229200/96229123/9ec5b924_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Princess Senses The Mangrove Resort - Adults Only Industry Cove Green Island Hanover CA $1,113 CA $1,113 total Mar 8 - Mar 9 includes taxes & fees 9/10 Wonderful! (436 reviews) Room was spotless, spacious and clean Reviewed on Feb 10, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&selected=96229123&PinnedHotelID=96229123&HadPinnedHotel=true®ionId=553248635975854330) ![Deja Resort All Inclusive](https://images.trvl-media.com/lodging/1000000/560000/554800/554709/6bc14513_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 $286 CA $338 total Mar 10 - Mar 11 includes taxes & fees 8/10 Very Good! (1,566 reviews) The staff was super nice and friendly … the drivers where so helpful I will deff come back Reviewed on Feb 4, 2026 [](https://expedia.ca/Hotel-Search?startDate=10%2F03%2F2026&endDate=11%2F03%2F2026&selected=554709&PinnedHotelID=554709&HadPinnedHotel=true®ionId=553248635975854330) [See all 1,536 properties in Middlesex](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=14%2F02%2F2026&endDate=15%2F02%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