Title: Highland Vacation Packages & Trips 2026 from CA $1,022 | 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 Inn At Fox Hollow Hotel](https://images.trvl-media.com/lodging/1000000/880000/871900/871849/c9a40759_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Inn At Fox Hollow Hotel CA $1,022 per person Jun 14 - Jun 18 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9.2/10 Wonderful! (1,011 reviews) Such a charming hotel with wonderful rooms. The Resturant and food are fabulous! Reviewed on Mar 18, 2026 ![WestHouse New York](https://images.trvl-media.com/lodging/7000000/6470000/6468000/6467973/a11ba963_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### WestHouse New York Manhattan CA $1,979 per person Jun 5 - Jun 9 found 1 day ago Roundtrip flight included Toronto (YTO) to Newark Liberty Intl. Airport (EWR) 8.4/10 Very Good! (1,006 reviews) Very quiet hotel in the heart of manhattan. Lovely rooms that were quite large by NYC standards. Bed was comfortable. Room well appointed. Could use more thoughtful lighting in areas where you unpack luggage, and lobby bar closure a little disappointing. However the breakfast was absolutely excellent and the evening appetizer and cocktail time a very nice addition to the stay. Definitely a hidden gem! Would for sure stay again. Reviewed on Mar 21, 2026 ![Interfaith 21](https://images.trvl-media.com/lodging/116000000/115480000/115476300/115476207/fd36e851_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Interfaith 21 Manhattan CA $1,213 per person Jun 14 - Jun 18 found 1 day ago Roundtrip flight included Toronto (YTO) to Newark Liberty Intl. Airport (EWR) 8.6/10 Excellent! (32 reviews) The room was very clean and staff super friendly! Recommended! Reviewed on Mar 20, 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 $3,748 per person May 31 - Jun 5 found 19 hours ago Roundtrip non-stop flight included Vancouver (YVR) 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 ![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 $1,033 per person May 30 - Jun 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Newark Liberty Intl. Airport (EWR) 9/10 Wonderful! (2,931 reviews) The staff were terrific,, accessible and welcoming... Rooms were kept so clean. Staff at the breakfast buffet were gracious and helpful... Great location... Will be back... Michael & Sarah C. Reviewed on Mar 26, 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 $116 CA $130 total Apr 16 - Apr 17 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=16%2F04%2F2026&endDate=17%2F04%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 $165 CA $185 total Mar 29 - Mar 30 includes taxes & fees 7.6/10 Good! (1,000 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=29%2F03%2F2026&endDate=30%2F03%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 $160 CA $186 total Apr 20 - Apr 21 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=20%2F04%2F2026&endDate=21%2F04%2F2026&selected=1927088&PinnedHotelID=1927088&HadPinnedHotel=true®ionId=115050) [See all 1,530 properties in Highland](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=28%2F03%2F2026&endDate=29%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