Title: Highland Vacation Packages & Trips 2026 from CA $1,367 | Expedia.ca [Hotels in Highland](https://expedia.ca/Highland-Hotels.d115050.Travel-Guide-Hotels)[Vacation Rentals in Highland](https://expedia.ca/Highland-Vacation-Rentals.d115050.Travel-Guide-VacationRentals)[Highland Car Rentals](https://expedia.ca/Car-Rentals-In-Highland.d115050.Car-Rental-Guide) ![](https://images.trvl-media.com/place/115050/b32ec179-9506-4b41-93f2-d2bb1696fa06.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Highland 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 Highland Vacation Reserve a Highland vacation package and get set to experience all this city has to offer. Consider basing yourself in the neighborhood of Poughkeepsie Waterfront, which is great for families, history and culture. If sightseeing is on the to-do list during your trip to Highland, swing by well-known attractions like [Walkway Over the Hudson State Historic Park](https://www.expedia.ca/Walkway-Over-The-Hudson-State-Historic-Park-New-York.d6222117.Vacation-Attraction), [Franklin D Roosevelt Library & Museum](https://www.expedia.ca/Franklin-D-Roosevelt-Library-Museum-Highland.d553248621533116643.Vacation-Attraction) and [Apple Greens Golf Course](https://www.expedia.ca/Apple-Greens-Golf-Course-Highland.d553248621559724941.Vacation-Attraction). Check out Expedia's wide range of travel options and book your dream vacation to Highland now. ## Top Highland Vacation Deals Price found within the past 48 hours. Click for updated prices. ![The Ridge Hotel](https://images.trvl-media.com/lodging/2000000/1790000/1785000/1784927/28d93ae4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Ridge Hotel Manhattan CA $1,367 per person Jun 8 - Jun 14 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Newark Liberty Intl. Airport (EWR) 8.2/10 Very Good! (1,032 reviews) Room small but clean. Staff were great, friendly and helpful. Reviewed on Mar 21, 2026 ![1 Hotel Brooklyn Bridge](https://images.trvl-media.com/lodging/16000000/15400000/15399700/15399642/b1e6b86c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel Brooklyn Bridge CA $1,812 per person Jun 19 - Jun 21 found 8 hours ago Roundtrip flight included Toronto (YYZ) to Newark Liberty Intl. Airport (EWR) 8.8/10 Excellent! (1,000 reviews) Excellent staff, clean room, fantastic onsite restaurants. Reviewed on Mar 10, 2026 ![Arthouse Hotel New York City](https://images.trvl-media.com/lodging/1000000/20000/12200/12117/0e6cbb94_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Arthouse Hotel New York City Manhattan CA $1,662 per person Jun 8 - Jun 14 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Newark Liberty Intl. Airport (EWR) 8.8/10 Excellent! (1,843 reviews) Wish there were fridges in all of the rooms. Front desk were super polite and helpful. Reviewed on Mar 25, 2026 ![Park Central Hotel New York](https://images.trvl-media.com/lodging/1000000/10000/4200/4164/cb48c512_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Central Hotel New York Manhattan CA $1,569 per person Jun 8 - Jun 14 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Newark Liberty Intl. Airport (EWR) 7.6/10 Good! (3,962 reviews) The carpet stunk other than that good. Reviewed on Mar 25, 2026 ![Hotel Riu Plaza New York Times Square](https://images.trvl-media.com/lodging/12000000/11680000/11677800/11677770/136f5a69_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza New York Times Square Manhattan CA $2,576 per person Jun 8 - Jun 14 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Newark Liberty Intl. Airport (EWR) 9/10 Wonderful! (2,931 reviews) Very clean room, amazing staff! They were extremely polite and quick to check in! The cleaning staff was great and friendly and everyone there seemed to enjoy their jobs which makes for a great environment! Will definitely stay again, the only downside is parking which is out of their control. I highly recommend staying and getting a room with a view! Reviewed on Mar 24, 2026 ## Ready to book your vacation to Highland? Choose your dates ## Highland Hotel Deals ![SureStay Plus Hotel by Best Western Highland Poughkeepsie](https://images.trvl-media.com/lodging/1000000/920000/918800/918797/11ffbd82_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### SureStay Plus Hotel by Best Western Highland Poughkeepsie 3423 US Highway 9W Highland NY Fully refundableReserve now, pay when you stay CA $110 CA $123 total Mar 29 - Mar 30 includes taxes & fees 7.8/10 Good! (979 reviews) The place was very clean and the staff was wonderful. Also a very nice breakfast choice included. Would stay there again. Reviewed on Mar 16, 2026 [](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=918797&PinnedHotelID=918797&HadPinnedHotel=true®ionId=115050) ![Best Western Plus Kingston Hotel And Conference Center](https://images.trvl-media.com/lodging/1000000/10000/6100/6056/d26fbbb0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Plus Kingston Hotel And Conference Center 503 Washington Ave Kingston NY Fully refundableReserve now, pay when you stay CA $131 CA $147 total Mar 31 - Apr 1 includes taxes & fees 7.6/10 Good! (1,004 reviews) There was a mystery pill found on the floor in the room. Lucky my dog didnt eat it. Still taking him to the vet. The hotel staff had nothing to say about it and even tried to take away the evidence. Also, anyone can walk in and wander around. Doors open without a key. Reviewed on Mar 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=31%2F03%2F2026&endDate=01%2F04%2F2026&selected=6056&PinnedHotelID=6056&HadPinnedHotel=true®ionId=115050) ![Hampton Inn & Suites Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/ee108dad_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn & Suites Poughkeepsie 2361 South Rd Poughkeepsie NY Fully refundableReserve now, pay when you stay CA $145 CA $169 total Apr 2 - Apr 3 includes taxes & fees 9/10 Wonderful! (1,000 reviews) Clean room with comfortable bed and nice bathroom. Friendly staff. Reviewed on Mar 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=02%2F04%2F2026&endDate=03%2F04%2F2026&selected=1927088&PinnedHotelID=1927088&HadPinnedHotel=true®ionId=115050) [See all 1,538 properties in Highland](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=26%2F03%2F2026&endDate=27%2F03%2F2026®ionId=115050) 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) ### What to do in Highland ![Bear Mountain State Park+ BeaconTown 1-Day Tour From NY](https://mediaim.expedia.com/localexpert/50302489/1ceb0837-f410-471c-80a4-908b6cbc0dd2.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Bear Mountain State Park+ BeaconTown 1-Day Tour From NY CA $129 per adult [](https://expedia.ca/things-to-do/bear-mountain-state-park-beacontown-1-day-tour-from-ny.a50302489.activity-details) [See all activities in Highland](https://expedia.ca/things-to-do/search?rid=115050) ## 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