Title: Book the Best Highland FAMILY FRIENDLY Hotels from CA $107 - Kid-Friendly Hotels in Highland, NY | 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 Family Hotels in Highland, NY from CA $107 - ![](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 Family Hotels Tonight [Oct 31 - Nov 1](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2025-10-31&endDate=2025-11-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Tomorrow [Nov 1 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2025-11-01&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) ## Top Highland Family Hotels ![Reception](https://images.trvl-media.com/lodging/1000000/920000/918800/918797/960f4844.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking, Refrigerator (with Sofabed)](https://images.trvl-media.com/lodging/1000000/920000/918800/918797/11ffbd82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/920000/918800/918797/18c05883.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/920000/918800/918797/d6363a59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SureStay Plus Hotel by Best Western Highland Poughkeepsie Highland 7.8/10 Good (913) "Room was clean, staff was exceptional. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) AnnaMaria CA $100 CA $112 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Poughkeepsie-Hotels-SureStay-Plus-Hotel-By-Best-Western-Highland-Poughkeepsie.h918797.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90260000/90253400/90253316/w910h683x57y0-c820193c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/91000000/90260000/90253400/90253316/2802b2bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/91000000/90260000/90253400/90253316/dbbcd386.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90260000/90253400/90253316/w914h683x56y0-13ef3179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley Highland 10/10 Exceptional (1) "Everyone was just right! The home is perfect for a photo shoot. We weren't there for that, but we thought the setting was unique and beautiful! Everything we needed!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca D. CA $280 CA $592 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Highland-Hotels-Step-Into-History-Unwind-At-Spring-Apt-A-Charming-At-Theof-NYHudson-Valley.h90253316.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/910000/906700/906700/ea4bff95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/910000/906700/906700/028cfcdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/910000/906700/906700/6fe2b40c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/910000/906700/906700/c9c03d80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Hyde Park Poughkeepsie North Hyde Park 8.0/10 Very good (1045) "GOOD STAY" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) TANISHA CA $94 CA $107 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Hyde-Park-Poughkeepsie-North.h906700.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/220000/216900/216870/d6a17faf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/220000/216900/216870/7271a3ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/220000/216900/216870/afb43ef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/220000/216900/216870/75a6f271.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus The Inn & Suites At The Falls Red Oaks Mill 7.8/10 Good (423) "Nice and quaint hotel with beautiful creek behind surrounded by a dorest" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hiram CA $147 CA $166 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Poughkeepsie-Hotels-Best-Western-Plus-The-Inn-Suites-At-The-Falls.h216870.Hotel-Information) ![Snack bar](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/ac7eba8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/a79c4292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Accessible, Non Smoking](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/47fa2e85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/56f73483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Poughkeepsie Crown Heights 8.8/10 Excellent (1005) "Excellent facility with great breakfast buffet." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $142 CA $165 total includes taxes & fees Nov 29 - Nov 30 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/1047d873.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 (1037) "Nice hotel with the lake view. The location is convenient and the price is affordable for a visit to West Point " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tuanh [](https://www.expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/100000000/99860000/99850800/99850733/w4000h2662x0y0-e2ffacae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/100000000/99860000/99850800/99850733/634879ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/100000000/99860000/99850800/99850733/1ee75d40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/100000000/99860000/99850800/99850733/w4000h2661x0y0-566be3f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Bellefield / Hyde Park, Residence Inn by Marriott Hyde Park 9.6/10 Exceptional (418) "Nice rooms, a good restaurant on site " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura CA $225 CA $255 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Hyde-Park-Hotels-Inn-At-Bellefield-Hyde-Park.h99850733.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/16000000/15720000/15715300/15715238/3f674783.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/16000000/15720000/15715300/15715238/ee573108.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/16000000/15720000/15715300/15715238/7e35994a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/16000000/15720000/15715300/15715238/8885aa53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Inn by Marriott Kingston Kingston 8.8/10 Excellent (769) "Very nice stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) LOIS CA $155 CA $174 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Kingston-Hotels-Residence-Inn-By-Marriott-Kingston.h15715238.Hotel-Information) ![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) ![Sports facility](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/2f2f704a.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 (1019) "Very clean and updated facilities " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashley CA $139 CA $157 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hilton-Garden-Inn-Fishkill.h890436.Hotel-Information) ![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) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/2000000/1370000/1364000/1363973/f976cd43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1370000/1364000/1363973/929cce76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Kingston Kingston 8.8/10 Excellent (1000) "Clean and comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lucinda CA $159 CA $178 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Kingston-Hotels-Courtyard-By-Marriott-Kingston.h1363973.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=2025-11-15&endDate=2025-11-16®ionId=115050&adults=2&travelerType=family_friendly&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 "Hotel was clean perfect for Over night stay" [](https://expedia.ca/Poughkeepsie-Hotels-Americas-Best-Value-Inn-New-Paltz.h897882.Hotel-Information) ![Beekman Arms Hotel](//images.trvl-media.com/lodging/13000000/12620000/12611900/12611810/ab673905_y.jpg) ### Beekman Arms Hotel 10/10 Excellent "lovely stay. its not perfect but has so much charm. It was like stepping back in time for the night!" [](https://expedia.ca/Poughkeepsie-Hotels-Beekman-Arms-Hotel.h12611810.Hotel-Information) ![Minnewaska Lodge](//images.trvl-media.com/lodging/2000000/1210000/1201800/1201707/3be04d40_y.jpg) ### Minnewaska Lodge 10/10 Excellent "Excellent stay❤️😀" [](https://expedia.ca/Poughkeepsie-Hotels-Minnewaska-Lodge.h1201707.Hotel-Information) ![Quality Inn Hyde Park Poughkeepsie North](//images.trvl-media.com/lodging/1000000/910000/906700/906700/ea4bff95_y.jpg) ### Quality Inn Hyde Park Poughkeepsie North 10/10 Excellent "GOOD STAY" [](https://expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Hyde-Park-Poughkeepsie-North.h906700.Hotel-Information) ![SureStay Plus Hotel by Best Western Highland Poughkeepsie](//images.trvl-media.com/lodging/1000000/920000/918800/918797/960f4844_y.jpg) ### SureStay Plus Hotel by Best Western Highland Poughkeepsie 10/10 Excellent "Clean room friendly staff " [](https://expedia.ca/Poughkeepsie-Hotels-SureStay-Plus-Hotel-By-Best-Western-Highland-Poughkeepsie.h918797.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 "Ashley was very helpful!" [](https://expedia.ca/Poughkeepsie-Hotels-Holiday-Inn-Express-Poughkeepsie.h12157.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 "Everything PERFECT " [](https://expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.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 "Everything was good the ev charging was great! " [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information) ![Quality Inn & Suites Fishkill South near I-84](//images.trvl-media.com/lodging/2000000/1770000/1766700/1766609/12805cb0_y.jpg) ### Quality Inn & Suites Fishkill South near I-84 10/10 Excellent "Nice stay. Easy check-in. " [](https://expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Suites-Fishkill-South-Near-I-84.h1766609.Hotel-Information) ## Frequently asked questions ### What's Highland like for family-friendly vacations? > If you've been thinking about a vacation with your kids, Highland is a good choice. The boating, sunny weather, and wildlife are just a few things that make this an attractive vacation spot for families. Fly into Stewart Intl. Airport (SWF), which is located 16.6 mi (26.7 km) from the city center. ### When's the best time to book a family-friendly vacation in Highland? > 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. ### What's there to see and do with your family in Highland? > While you and your family are staying in Highland, you might want to visit some family-friendly attractions such as Franklin D Roosevelt Library & Museum, Bardavon 1869 Opera House, and Home of Franklin D. Roosevelt National Historic Site. Make sure you have lots of time for activities like Franklin D. 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