Title: Hillsdale Vacation Packages & Trips 2026 from CA $988 | Expedia.ca [Hillsdale Travel Guide](https://expedia.ca/Hillsdale.dx183683)[Hotels in Hillsdale](https://expedia.ca/Hillsdale-Hotels.d183683.Travel-Guide-Hotels)[Vacation Rentals in Hillsdale](https://expedia.ca/Hillsdale-Vacation-Rentals.d183683.Travel-Guide-VacationRentals)[Hillsdale Car Rentals](https://expedia.ca/Car-Rentals-In-Hillsdale.d183683.Car-Rental-Guide) ![](https://images.trvl-media.com/place/183683/35d7f921-3f97-4c8a-8510-c7d3e01cb58c.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Hillsdale 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 Hillsdale Vacation The rich history and welcoming locals are just the beginning of the things Hillsdale has to offer. Experience the sights and sounds of this captivating city the way you want with a customized Hillsdale vacation package. Every trip to Hillsdale just has to include a bit of sightseeing. Where to first? [Catamount Aerial Adventure Park](https://www.expedia.ca/Catamount-Aerial-Adventure-Park-Hillsdale.d553248621532664791.Vacation-Attraction) and [Taconic State Park](https://www.expedia.ca/Taconic-State-Park-New-York.d553248621532664790.Vacation-Attraction) are key attractions. Whatever your travel plans or the size of your budget, organizing your ultimate tailored Hillsdale vacation is easy with Expedia. ## Top Hillsdale Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Weathervane Motel](https://images.trvl-media.com/lodging/11000000/10430000/10429400/10429394/17ddc189_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Weathervane Motel CA $988 per person May 22 - May 25 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Albany (ALB) 6.8/10 (753 reviews) Courteous staff and clean rooms. Reviewed on Mar 1, 2026 ![The Manchester View](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/738a0d56_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Manchester View CA $1,254 per person May 22 - May 25 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Albany (ALB) 9.4/10 Exceptional! (818 reviews) Beautiful property, clean room, friendly staff. Will definitely be staying here again! Reviewed on Mar 18, 2026 ![Aspen At Manchester](https://images.trvl-media.com/lodging/11000000/10260000/10254500/10254459/cbf700aa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Aspen At Manchester CA $1,192 per person May 22 - May 25 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Albany (ALB) 8.8/10 Excellent! (637 reviews) Great room very clean Reviewed on Mar 1, 2026 ![Toll Road Inn](https://images.trvl-media.com/lodging/8000000/7660000/7652200/7652200/94368990_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Toll Road Inn CA $1,186 per person May 22 - May 25 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Albany (ALB) 9/10 Wonderful! (504 reviews) Nice property by the river. Cozy places. Big rooms! Reviewed on Mar 19, 2026 ![Four Winds Country Motel](https://images.trvl-media.com/lodging/8000000/7650000/7640900/7640832/c7e6e735_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Four Winds Country Motel CA $1,091 per person May 22 - May 25 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Albany (ALB) 8.4/10 Very Good! (539 reviews) The room was spotless, and the staff was very king. Reviewed on Feb 28, 2026 ## Ready to book your vacation to Hillsdale? Choose your dates ## Hillsdale Hotel Deals ![The Brooks Motel](https://images.trvl-media.com/lodging/97000000/97000000/96999600/96999590/7554b9b1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Brooks Motel 2871 New York 23 Hillsdale NY Fully refundableReserve now, pay when you stay CA $150 CA $169 total Apr 5 - Apr 6 includes taxes & fees 7.4/10 Good! (133 reviews) Room was clean Reviewed on Feb 27, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=96999590&PinnedHotelID=96999590&HadPinnedHotel=true®ionId=183683) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Berkshire Mountain Lodge 8 Dan Fox Dr Pittsfield MA Fully refundableReserve now, pay when you stay CA $120 CA $165 total Apr 26 - Apr 27 includes taxes & fees 9/10 Wonderful! (888 reviews) very clean and friendly staff Reviewed on Mar 24, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F04%2F2026&endDate=27%2F04%2F2026&selected=11449113&PinnedHotelID=11449113&HadPinnedHotel=true®ionId=183683) ![Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy](https://images.trvl-media.com/lodging/110000000/109130000/109129600/109129528/d4631129_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy 282 Cairo Junction Rd Catskill NY CA $193 CA $268 total Apr 13 - Apr 14 includes taxes & fees 9.6/10 Exceptional! (183 reviews) The plane is so beautiful and relaxing Reviewed on Mar 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=13%2F04%2F2026&endDate=14%2F04%2F2026&selected=109129528&PinnedHotelID=109129528&HadPinnedHotel=true®ionId=183683) [See all 1,845 properties in Hillsdale](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=28%2F03%2F2026&endDate=29%2F03%2F2026®ionId=183683) 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