Title: Book the Best HISTORIC Hotels in Highland in 2025 | 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 # Find Historic Hotels in Highland, NY from CA $147 - ![](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 [Nov 30 - Dec 1](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2025-11-30&endDate=2025-12-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 1 - Dec 2](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2025-12-01&endDate=2025-12-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Highland Historic Hotels ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/2b66e26d.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) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/a90c96fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Poughkeepsie Poughkeepsie 8.8/10 Excellent (1010) "Clean room, staff is friendly especially at the cafe. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cynthia CA $130 CA $147 total includes taxes & fees Dec 21 - Dec 22 [](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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/w3831h2553x9y7-9c25ee45.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/1000000/120000/119300/119273/8529e0e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/0c0edcb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Fishkill Fishkill 8.6/10 Excellent (1003) "Was a great experience " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) george CA $133 CA $151 total includes taxes & fees Dec 12 - Dec 13 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Fishkill.h119273.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71560000/71554400/71554330/d66159f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71560000/71554400/71554330/8f636fec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Hot Tub - Fire Pit - BBQ - Hammock - Colonial Kingston 9.4/10 Exceptional (22) "This was a great stay away, just for a couple of quiet days. Inside the house was excellent. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dennis M. CA $120 CA $322 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Kingston-Hotels-Charming-Hudson-Valley-Luxury-Getaway.h71554330.Hotel-Information) ![Hypo-allergenic bedding, free WiFi, bed sheets](https://images.trvl-media.com/lodging/16000000/15010000/15001800/15001782/76c6b6d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/16000000/15010000/15001800/15001782/43e2acce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, 2 Double Beds, Accessible (No pets)](https://images.trvl-media.com/lodging/16000000/15010000/15001800/15001782/be389ef5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/16000000/15010000/15001800/15001782/9ce10fed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Roosevelt Inn of Hyde Park Hyde Park 9.4/10 Exceptional (550) "A very comfortable room, along with a good continental breakfast in their cute little shop. We'd definitely stay there again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Beth CA $160 CA $181 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Poughkeepsie-Hotels-Roosevelt-Inn-Of-Hyde-Park.h15001782.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/31000000/30530000/30528700/30528653/1d436988.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/31000000/30530000/30528700/30528653/89b9b977.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/31000000/30530000/30528700/30528653/41817d7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Suite, Non Smoking](https://images.trvl-media.com/lodging/31000000/30530000/30528700/30528653/93e32325.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn the Woods Bed and Breakfast Hyde Park 9.8/10 Exceptional (135) "Harry was great, room clean and fresh, breakfast amazing " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frank CA $256 CA $289 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Poughkeepsie-Hotels-Inn-The-Woods-Bed-And-Breakfast.h30528653.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/68000000/67270000/67268600/67268558/b528caee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/68000000/67270000/67268600/67268558/677d2235.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/68000000/67270000/67268600/67268558/bd8601b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/68000000/67270000/67268600/67268558/a55bcd48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Omega special, Sunday night thru Thursday night 5 NIGHT MINIMUM, 3 miles away, Clinton Corners 8.2/10 Very good (11) "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 $196 CA $272 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Poughkeepsie-Hotels-Private-Bed-Bath-On-Secluded-30-Acre-Farm.h67268558.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/ab271dba.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) ![Exterior detail](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/04adf8dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/70000000/69250000/69240100/69240003/13b54d67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer Beacon 10/10 Exceptional (47) "Great room and location. A nice home base for exploring the area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bob G. CA $157 CA $340 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Beacon-Hotels-Luxe-Studio-4-On-Main-Street-Luxury-Steam-Shower.h69240003.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/69000000/68780000/68773100/68773092/c736a539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/69000000/68780000/68773100/68773092/6d7fbb92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private room on secluded 7 acres , access to entire house including patio, porch Clinton Corners 8.6/10 Excellent (30) "It was just as advertised! Host was nice included fruit and coffee " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) matt w. CA $210 CA $289 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Clinton-Corners-Hotels-Private-Room-On-Secluded-7-Acres.h68773092.Hotel-Information) ![Hiking](https://images.trvl-media.com/lodging/18000000/17910000/17902100/17902038/c194d854.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/18000000/17910000/17902100/17902038/731ceae3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/18000000/17910000/17902100/17902038/e86f8756.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/18000000/17910000/17902100/17902038/6ae0b5c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Journey Inn Bed & Breakfast Hyde Park 9.6/10 Exceptional (336) "Great staff, the breakfast was amazing, location to surrounding attractions was great! I would stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shawn CA $313 CA $354 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Poughkeepsie-Hotels-Journey-Inn-Bed-Breakfast.h17902038.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/40000000/40000000/39997000/39996972/10e984da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/40000000/40000000/39997000/39996972/16ad15d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/40000000/40000000/39997000/39996972/7c8a09e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/40000000/40000000/39997000/39996972/4146f75f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Church Des Artistes a Hudson Valley retreat Rondout 9.8/10 Exceptional (10) "Beautiful, unique stay! Julie was really kind walking us through the ins and outs of the property during check-in. So much care and attention put into every room. And the book collection is amazing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Molly M. CA $1,887 CA $3,308 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Kingston-Hotels-Church-Des-Artistes-A-Hudson-Valley-Retreat.h39996972.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=2025-12-14&endDate=2025-12-15®ionId=115050&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_115050) ## Top Highland Hotel Reviews ![Hampton Inn & Suites Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/47fa2e85_y.jpg) ### Hampton Inn & Suites Poughkeepsie 10/10 Excellent "The staff was very nice and accommodating. The room was perfect and the bed was super comfortable. Will stay again if in the area." [](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 "Very nice place where they cater to everyone as more than a guest, Staff wonderful. Quiet location, so not many choices for restaurants. " [](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/d4db98bc_y.jpg) ### Best Western Plus Kingston Hotel And Conference Center 10/10 Excellent "Room was good, staff pleasant. The cancelled free breakfasts adding a daily charge but since i booked before then i received free breakfast coupons for each morning. Have to check every BW visit in future though. " [](https://expedia.ca/Kingston-Hotels-Best-Western-Plus-Kingston-Hotel-And-Conference-Center.h6056.Hotel-Information) ![Holiday Inn Express Poughkeepsie by IHG](https://images.trvl-media.com/lodging/1000000/20000/12200/12157/9d729415_y.jpg) ### Holiday Inn Express Poughkeepsie by IHG 10/10 Excellent "Staff was great. Rooms were updated. Shower heads were the big rain shower type. The beds were comfortable, not too soft. Breakfast buffet was a notch above others. " [](https://expedia.ca/Poughkeepsie-Hotels-Holiday-Inn-Express-Poughkeepsie.h12157.Hotel-Information) ![Courtyard by Marriott Poughkeepsie](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2_y.jpg) ### Courtyard by Marriott Poughkeepsie 10/10 Excellent "Pleasant staff and clean room." [](https://expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information) ![Hampton Inn Kingston](https://images.trvl-media.com/lodging/2000000/1670000/1662000/1661941/21cb7965_y.jpg) ### Hampton Inn Kingston 10/10 Excellent "friendly staffg" [](https://expedia.ca/Kingston-Hotels-Hampton-Inn-Kingston.h1661941.Hotel-Information) ![DoubleTree by Hilton Poughkeepsie Convention Center](https://images.trvl-media.com/lodging/1000000/20000/14600/14563/acc87956_y.jpg) ### DoubleTree by Hilton Poughkeepsie Convention Center 10/10 Excellent "The room was very spotless and the restaurant food was great 👍 I'm looking forward to next year trip " [](https://expedia.ca/Poughkeepsie-Hotels-Poughkeepsie-Grand-Hotel.h14563.Hotel-Information) ![SureStay Plus Hotel by Best Western Highland Poughkeepsie](https://images.trvl-media.com/lodging/1000000/920000/918800/918797/960f4844_y.jpg) ### SureStay Plus Hotel by Best Western Highland Poughkeepsie 10/10 Excellent "Nice room, nice staff" [](https://expedia.ca/Poughkeepsie-Hotels-SureStay-Plus-Hotel-By-Best-Western-Highland-Poughkeepsie.h918797.Hotel-Information) ![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/e8f6eb1b_y.jpg) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point 10/10 Excellent "Very friendly front desk staff!" [](https://expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ## Frequently asked questions ### What should a history buff expect from a stay in Highland? > The historical places in Highland are likely a big part of your travel plans. While you are here in this family-friendly area, why not also discover all of the sights in the area? ### How many historical hotels are there in Highland? > In Highland, you'll find 39 hotel accommodations bookable on Expedia but not many designated as historic hotels. ### What are the top historical sites and other places to visit in Highland? > Highland is notable for landmarks like Walkway Over the Hudson State Historic Park. A couple of additional sights to add to your agenda are Franklin D Roosevelt Library & Museum and Berean Park Beach. ### What is a historic hotel like in Highland? > Guests who book a historic hotel can stay in a building that has an officially recognized historic designation. A stately home, palace or even a lodge, old police station, or skyscraper can be identified as a historic hotel as long as it's of special interest. Traditional architecture and period features are often preserved in the communal spaces and guestrooms of historic hotels in Highland, giving a historical feel. ### What is the difference between a historic hotel and a heritage hotel? > "Heritage hotel" is more common in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. but overall the terms are quite similar. The physical building and architecture of historic hotels tend to be what's most important. For a heritage hotel, it's mainly the cultural value and how it shaped the community. ### Do historic hotels in Highland have modern facilities? > Hotels include modern conveniences and safety features you've come to expect, though efforts have been made to preserve treasured traditions and historic facades. Private rooms with updated bathroom facilities, heating and air conditioning, free and fast Internet, and the popular amenities found at a contemporary hotel will be available in a historic hotel. When you choose a historic hotel in Highland, don't worry that you'll find a place that's uncomfortable for guests or simply rundown. ## 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) - [Hotels with Bar in Albany](https://www.expedia.ca/Albany-Hotels-Hotels-With-Bar.0-0-d603260-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Hotels with Tennis Courts in Albany](https://www.expedia.ca/Albany-Hotels-Hotels-With-Tennis-Courts.0-0-d603260-tHotelswithTennisCourts.Travel-Guide-Filter-Hotels) - [Ski Hotels in Albany](https://www.expedia.ca/Albany-Hotels-Ski-Hotel.0-0-d603260-tSkiHotel.Travel-Guide-Filter-Hotels) - 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