Title: Book the Best HISTORIC Hotels in Highland in 2026 | 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)[Highland Vacation Packages](https://expedia.ca/Highland.d115050.Destination-Travel-Guides) ![Walking across the walkway over the Hudson, get there early to avoid parking issues. Great place to walk your dog!](https://images.trvl-media.com/place/115050/513f001c-86fc-4f9b-8930-057b5d34aed2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Allison Alano Flores ![](https://images.trvl-media.com/place/115050/513f001c-86fc-4f9b-8930-057b5d34aed2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Highland Historic Hotels Tonight [Mar 12 - Mar 13](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2026-03-12&endDate=2026-03-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 13 - Mar 14](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2026-03-13&endDate=2026-03-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2026-03-13&endDate=2026-03-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2026-03-20&endDate=2026-03-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Highland historic hotels ![Smart TV](https://images.trvl-media.com/lodging/72000000/71560000/71554400/71554330/caba39f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/72000000/71560000/71554400/71554330/f2a122ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71560000/71554400/71554330/248767ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71560000/71554400/71554330/d66159f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hot Tub - Fire Pit - BBQ - Hammock - Colonial [](https://www.expedia.ca/Kingston-Hotels-Charming-Hudson-Valley-Luxury-Getaway.h71554330.Hotel-Information) Kingston 9.6/10 Exceptional (25 reviews) "The rental was very clean & Beds were very comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) R.A.G. Time A. CA $122 CA $320 total includes taxes & fees Mar 17 - Mar 18 [](https://www.expedia.ca/Kingston-Hotels-Charming-Hudson-Valley-Luxury-Getaway.h71554330.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/04adf8dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/19de180c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/a8c5ab99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/c6f43c54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer [](https://www.expedia.ca/Beacon-Hotels-Luxe-Studio-4-On-Main-Street-Luxury-Steam-Shower.h69240003.Hotel-Information) Beacon 10/10 Exceptional (54 reviews) "We havld a good time. The room was comfortable and perfectly located!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandy C. CA $156 CA $340 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Beacon-Hotels-Luxe-Studio-4-On-Main-Street-Luxury-Steam-Shower.h69240003.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/69000000/68780000/68773100/68773092/447949bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/69000000/68780000/68773100/68773092/8e24845d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/69000000/68780000/68773100/68773092/1941c471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/69000000/68780000/68773100/68773092/f31a431f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private room on secluded 7 acres , access to entire house including patio, porch [](https://www.expedia.ca/Clinton-Corners-Hotels-Private-Room-On-Secluded-7-Acres.h68773092.Hotel-Information) Clinton Corners 8.6/10 Excellent (30 reviews) "This place is a museum spotless." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kris A J. CA $204 CA $278 total includes taxes & fees Mar 21 - Mar 22 [](https://www.expedia.ca/Clinton-Corners-Hotels-Private-Room-On-Secluded-7-Acres.h68773092.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/68000000/67270000/67268600/67268558/9224e1b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/68000000/67270000/67268600/67268558/b338553a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/68000000/67270000/67268600/67268558/aeb97fc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/68000000/67270000/67268600/67268558/b528caee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Omega special, Sunday night thru Thursday night 5 NIGHT MINIMUM, 3 miles away, [](https://www.expedia.ca/Poughkeepsie-Hotels-Private-Bed-Bath-On-Secluded-30-Acre-Farm.h67268558.Hotel-Information) Clinton Corners 8.2/10 Very good (11 reviews) "The propert my, grounds and location is just charming. Hosts were stellar and welcoming. Accomodations warm and inviting." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dawn B. CA $204 CA $278 total includes taxes & fees Mar 21 - Mar 22 [](https://www.expedia.ca/Poughkeepsie-Hotels-Private-Bed-Bath-On-Secluded-30-Acre-Farm.h67268558.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/14b3dc77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/1765b81e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/9a6a049d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Poughkeepsie [](https://www.expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information) Poughkeepsie 8.8/10 Excellent (1,000 reviews) "Wonderful, quiet stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erinn CA $143 CA $162 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/f57ee72e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/f3387c76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/de450357.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/c73b0205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Fishkill [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Fishkill.h119273.Hotel-Information) Fishkill 8.6/10 Excellent (1,000 reviews) "Clean room and friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jonathan CA $138 CA $160 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Fishkill.h119273.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/67000000/66610000/66603200/66603127/ce451532.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66610000/66603200/66603127/e2a7f284.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/67000000/66610000/66603200/66603127/83edf1c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, stereo, offices](https://images.trvl-media.com/lodging/67000000/66610000/66603200/66603127/b30ea75d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Woodstock Historic Artist Estate - The Museum House [](https://www.expedia.ca/Kingston-Hotels-Vrbo-Property.h66603127.Hotel-Information) Woodstock 9.8/10 Exceptional (9 reviews) "We had a short stay but absolutely loved the house. Perfect location, lots of space, and the hosts were great. Would stay again, highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Strati P. CA $744 CA $1,301 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Kingston-Hotels-Vrbo-Property.h66603127.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-03-26&endDate=2026-03-27®ionId=115050&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ![](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=AFFINITY_SPRING_PROMO_115050) ## Top Highland Hotel Reviews ![Courtyard by Marriott Poughkeepsie](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2_y.jpg) ### Courtyard by Marriott Poughkeepsie 10/10 Excellent "Jenis was a great help " [](https://expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information) ![SureStay Plus Hotel by Best Western Highland Poughkeepsie](https://images.trvl-media.com/lodging/1000000/920000/918800/918797/11ffbd82_y.jpg) ### SureStay Plus Hotel by Best Western Highland Poughkeepsie 10/10 Excellent "Tv stopped working at 10pm" [](https://expedia.ca/Poughkeepsie-Hotels-SureStay-Plus-Hotel-By-Best-Western-Highland-Poughkeepsie.h918797.Hotel-Information) ![Hampton Inn & Suites Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/ee108dad_y.jpg) ### Hampton Inn & Suites Poughkeepsie 6/10 Okay "We found a bug in our bed. Using Google image it was identified as a bed bug. We went to the front desk and they relocated us to a different floor and upgraded us to a suite. It left us uneasy but we were happy the staff took us seriously. " [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information) ![Minnewaska Lodge](https://images.trvl-media.com/lodging/2000000/1210000/1201800/1201707/3be04d40_y.jpg) ### Minnewaska Lodge 10/10 Excellent "We have now stayed at the lodge twice. It has been a relaxing, amazing stay both times!" [](https://expedia.ca/Poughkeepsie-Hotels-Minnewaska-Lodge.h1201707.Hotel-Information) ![Best Western Plus Kingston Hotel And Conference Center](https://images.trvl-media.com/lodging/1000000/10000/6100/6056/d26fbbb0_y.jpg) ### Best Western Plus Kingston Hotel And Conference Center 4/10 Poor "Wish there was a way to show when the pool is closed. We had a choice of similar hotels - selected this one based on location and our family likes to enjoy having access to a pool during a vacation. The hotel needs quite a bit of TLC - our room cleanliness was okay but there as a bad looking white stain in the chair. " [](https://expedia.ca/Kingston-Hotels-Best-Western-Plus-Kingston-Hotel-And-Conference-Center.h6056.Hotel-Information) ![Quality Inn Hyde Park Poughkeepsie North](https://images.trvl-media.com/lodging/1000000/910000/906700/906700/ea4bff95_y.jpg) ### Quality Inn Hyde Park Poughkeepsie North 6/10 Okay "We had no internet in our room for our entire stay. We asked about it and was told it was being servixes that day, it was nit fuxed and only worked in the lobby (our room was 20 ft from there)" [](https://expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Hyde-Park-Poughkeepsie-North.h906700.Hotel-Information) ![Spark by Hilton Fishkill](https://images.trvl-media.com/lodging/1000000/10000/2700/2642/b112328f_y.jpg) ### Spark by Hilton Fishkill 8/10 Good "Clean room; very small bathroom" [](https://expedia.ca/Fishkill-Hotels-Spark-By-Hilton-Fishkill.h2642.Hotel-Information) ![Beekman Arms and Delamater Inn](https://images.trvl-media.com/lodging/13000000/12620000/12611900/12611810/b86d31e8_y.jpg) ### Beekman Arms and Delamater Inn 10/10 Excellent "We've visited Beekman Arms numerous times. If you're someone who loves history and antiques, it's the place for you. What makes it a particular favorite, though, is the staff. " [](https://expedia.ca/Poughkeepsie-Hotels-Beekman-Arms-Hotel.h12611810.Hotel-Information) ![DoubleTree by Hilton Poughkeepsie Convention Center](https://images.trvl-media.com/lodging/1000000/20000/14600/14563/875b6b8c_y.jpg) ### DoubleTree by Hilton Poughkeepsie Convention Center 8/10 Good "Easy walk to nearby restaurants." [](https://expedia.ca/Poughkeepsie-Hotels-Poughkeepsie-Grand-Hotel.h14563.Hotel-Information) ## Frequently asked questions ### What should a history buff expect from a stay in Highland? ### How many historical hotels are there in Highland? ### What are the top historical sites and other places to visit in Highland? ### What is a historic hotel like in Highland? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in Highland have modern facilities? ## Explore a world of travel with Expedia - Lodging - Flights - More ways to book - [Business Hotels in Albany ](https://www.expedia.ca/Albany-Hotels-Business-Hotel.0-0-d603260-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Albany ](https://www.expedia.ca/Albany-Hotels-Couples-Resorts-Hotels.0-0-d603260-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Albany ](https://www.expedia.ca/Albany-Hotels-Hotel-With-Early-Check-In.0-0-d603260-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - 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