Title: Book the Best Hotels with POOL 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) ![](https://mediaim.expedia.com/destination/2/8639fd6b72242b4bb7d3755307a419d9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Karen Wirtz # Find Hotels with a Pool in Highland, NY from CA $141 ![](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 Hotels with a Pool Tonight [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2025-10-25&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2025-10-26&endDate=2025-10-27&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Highland Hotels with a Pool ![Indoor pool](https://images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/e4abb59f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/9bb388bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/c1f101cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/28ad5864.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Poughkeepsie / Hudson Valley Crown Heights 9.0/10 Wonderful (1003) "we stayed 2 nights midweek, very comfortable, quiet and everything was top notch!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) GARY CA $165 CA $192 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hyatt-Place-Poughkeepsie.h37960419.Hotel-Information) ![Sports facility](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/2f2f704a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/e1e7e350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/239951b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/459515b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Fishkill Fishkill 8.6/10 Excellent (1017) "It was a great place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda CA $149 CA $168 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hilton-Garden-Inn-Fishkill.h890436.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/e8f6eb1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/51570973.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/1047d873.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Accessible, Non Smoking](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/38401260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point New Windsor 8.4/10 Very good (1029) "Great hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeannine CA $137 CA $155 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/c695ef3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/130ec357.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/7472348e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 King Bed, Accessible (Hearing)](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/4eb66254.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites By Hilton Poughkeepsie Poughkeepsie 9.4/10 Exceptional (361) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $160 CA $185 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Poughkeepsie-Hotels-Home2-Suites-By-Hilton-Poughkeepsie.h103394153.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/bd59d6cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/dab27d3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/a9b4d40a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/bdaa6450.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn by Hilton New Paltz New Paltz 9.4/10 Exceptional (1004) "Excellent choice to stay at in this area" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donna CA $171 CA $192 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1370000/1364000/1363973/eab20864.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/2000000/1370000/1364000/1363973/f976cd43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/2000000/1370000/1364000/1363973/dccc054e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1370000/1364000/1363973/a5bfb382.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Kingston Kingston 8.8/10 Excellent (1004) "I ate breakfast at a diner near by but thr hotel is close to restaurants n stores noce place close to everything" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carlos CA $153 CA $172 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Kingston-Hotels-Courtyard-By-Marriott-Kingston.h1363973.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1670000/1662000/1661941/a45db9ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1670000/1662000/1661941/fcda508b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1670000/1662000/1661941/21cb7965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/2000000/1670000/1662000/1661941/df160e9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Kingston Kingston 9.0/10 Wonderful (1002) "Very friendly front desk staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ann CA $160 CA $179 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Kingston-Hotels-Hampton-Inn-Kingston.h1661941.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1690000/1680400/1680342/eb75ea57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Buffet](https://images.trvl-media.com/lodging/2000000/1690000/1680400/1680342/830db074.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1690000/1680400/1680342/38e2c556.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/2000000/1690000/1680400/1680342/33748891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Fishkill-Mid Hudson Valley by IHG Fishkill 8.4/10 Very good (1002) "Very good stay; as advertised." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $179 CA $203 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Poughkeepsie-Hotels-Holiday-Inn-Express-Fishkill-Mid-Hudson-Valley.h1680342.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/6500/6465/9bb5ee16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior Standard Room, 2 Double Beds, Non Smoking, Annex Building](https://images.trvl-media.com/lodging/1000000/10000/6500/6465/a647c710.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Vending machine](https://images.trvl-media.com/lodging/1000000/10000/6500/6465/3070b4a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/6500/6465/be375701.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Poughkeepsie Arlington 7.8/10 Good (460) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emily CA $121 CA $141 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Poughkeepsie.h6465.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/6100/6056/d26fbbb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/6100/6056/ac803c49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/6100/6056/36261342.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/6100/6056/d76cf1a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Kingston Hotel And Conference Center Kingston 7.6/10 Good (1049) "Convenient and close to everything " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sheikh CA $160 CA $179 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Kingston-Hotels-Best-Western-Plus-Kingston-Hotel-And-Conference-Center.h6056.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=2025-11-08&endDate=2025-11-09®ionId=115050&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Highland Hotel Reviews ![Americas Best Value Inn New Paltz](//images.trvl-media.com/lodging/1000000/900000/897900/897882/1c07aec9_y.jpg) ### Americas Best Value Inn New Paltz 10/10 Excellent "We enjoyed our stay, we thought there could have been more choices for breakfast. Like sausage or eggs, etc. Other than that, everything else was good." [](https://expedia.ca/Poughkeepsie-Hotels-Americas-Best-Value-Inn-New-Paltz.h897882.Hotel-Information) ![Hampton Inn & Suites Poughkeepsie](//images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/47fa2e85_y.jpg) ### Hampton Inn & Suites Poughkeepsie 10/10 Excellent "Hampton inn newly refurbished " [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information) ![Hampton Inn by Hilton New Paltz](//images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/bd59d6cb_y.jpg) ### Hampton Inn by Hilton New Paltz 10/10 Excellent "Clean room and facility. Excellent staff. Breakfast foods were a bit off - they should keep to basic, straight forward foods for breakfast (waffle batter doesn't need to be vanilla malt flavored). And use quality coffee......" [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information) ![HYATT house Fishkill/Poughkeepsie](//images.trvl-media.com/lodging/2000000/1340000/1336000/1335929/4a7fc30b_y.jpg) ### HYATT house Fishkill/Poughkeepsie 10/10 Excellent "All of the employees that we met were very kind, courteous, professional, and willing to help" [](https://expedia.ca/Poughkeepsie-Hotels-HYATT-House-FishkillPoughkeepsie.h1335929.Hotel-Information) ![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](//images.trvl-media.com/lodging/1000000/880000/875700/875625/e8f6eb1b_y.jpg) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point 10/10 Excellent "The view of the river from the front is beautiful. I would stay here again. " [](https://expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![Holiday Inn Express Poughkeepsie by IHG](//images.trvl-media.com/lodging/1000000/20000/12200/12157/9d729415_y.jpg) ### Holiday Inn Express Poughkeepsie by IHG 10/10 Excellent "Good breakfast with lits if choices. Quiet lication with ample free parking." [](https://expedia.ca/Poughkeepsie-Hotels-Holiday-Inn-Express-Poughkeepsie.h12157.Hotel-Information) ![Ramada by Wyndham Newburgh/West Point](//images.trvl-media.com/lodging/1000000/20000/11400/11304/98af6d38_y.jpg) ### Ramada by Wyndham Newburgh/West Point 10/10 Excellent "Everything was dirty. The staff was rude. I didn't want to walk on the floor without shoes in my room. I was refused an extra pillow. I was concerned for my safety as well. Would not recommend." [](https://expedia.ca/Newburgh-Hotels-Ramada-By-Wyndham-NewburghWest-Point.h11304.Hotel-Information) ![The Crossroads Hotel, Newburgh](//images.trvl-media.com/lodging/1000000/20000/14500/14410/5440914b_y.jpg) ### The Crossroads Hotel, Newburgh 10/10 Excellent "The perfect place for what we were asking. My brother and I stayed for one night as a stop on our travels further North. The staff was very pleasant, the room was clean, and parking was a breeze. We were able to grab dinner at the diner next door and we even went ice skating for an hour at the IceTime Sports Complex (a one minute drive) after dinner. We didn’t know what we’d be walking in to but it was an all around pleasant experience. " [](https://expedia.ca/Newburgh-Hotels-The-Crossroads-Hotel.h14410.Hotel-Information) ![Courtyard by Marriott Poughkeepsie](//images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2_y.jpg) ### Courtyard by Marriott Poughkeepsie 10/10 Excellent "Very clean, nice and convenient to get from car to room. My husband said they had the best shower water pressure he had ever experienced in his entire life. Lol. Awesome stay! Very quiet when we were there. " [](https://expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Highland? > [SureStay Plus Hotel by Best Western Highland Poughkeepsie](https://www.expedia.ca/Poughkeepsie-Hotels-SureStay-Plus-Hotel-By-Best-Western-Highland-Poughkeepsie.h918797.Hotel-Information): Features a full-service spa, a seasonal outdoor pool, and 3 bars. [The Crossroads Hotel, Newburgh](https://www.expedia.ca/Newburgh-Hotels-The-Crossroads-Hotel.h14410.Hotel-Information): Hotel, 7-minute walk from Vassar College. Offers daily, an indoor pool, and free self parking. [Hampton Inn & Suites Poughkeepsie](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information): Features a children's pool, an indoor pool, and free self parking. [Wildflower Farms, Auberge Collection](https://www.expedia.ca/Gardiner-Hotels-Wildflower-Farms.h79873064.Hotel-Information): Provides free self parking, an indoor pool, and complimentary wireless internet access. [Quality Inn Poughkeepsie](https://www.expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Poughkeepsie.h6465.Hotel-Information): Features buffet, an indoor pool, and complimentary wired internet access. ### What is there to see and do in Highland? > The picturesque setting of Walkway Over the Hudson State Historic Park and Berean Park Beach showcase the area's natural beauty. During your stay, check out sights such as Franklin D Roosevelt Library & Museum, Franny Reese State Park, and Apple Greens Golf Course. ### When is the best time to book a hotel with a pool in Highland? > Taking into account the local weather in Highland can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Highland are January, February, March, and April, with each month seeing an average of 7 inches of snowfall. ## 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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