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 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 5 - Oct 6](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2025-10-05&endDate=2025-10-06&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 6 - Oct 7](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2025-10-06&endDate=2025-10-07&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2025-10-10&endDate=2025-10-12&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2025-10-17&endDate=2025-10-19&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Highland Family Hotels ![Indoor pool](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/e8f6eb1b.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) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/51570973.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/6b6d035b.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 (1004) "Great price for a great hotel" CA $137 CA $155 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/2000000/1770000/1766700/1766609/12805cb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/2000000/1770000/1766700/1766609/1a25c0f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1770000/1766700/1766609/05914abb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1770000/1766700/1766609/a6ffa5e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn & Suites Fishkill South near I-84 Fishkill 8.8/10 Excellent (1008) "Clean, quiet, non-smoking and convenient. " CA $130 CA $148 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Suites-Fishkill-South-Near-I-84.h1766609.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/47637293.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/91f0a8ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hanlon Suite | Children's theme room](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/05c3d7b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/49ef52ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borland House Inn Montgomery 9.2/10 Wonderful (128) "Unique experience, very comfortable, clean and quaint" CA $143 CA $162 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Newburgh-Hotels-Borland-House-Inn.h11796055.Hotel-Information) ![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) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/920000/918800/918797/71c5e58e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SureStay Plus Hotel by Best Western Highland Poughkeepsie Highland 7.6/10 Good (894) "Room was clean, staff was exceptional. " CA $100 CA $112 total includes taxes & fees Nov 2 - Nov 3 [](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) ![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) ![Exterior](https://images.trvl-media.com/lodging/91000000/90260000/90253400/90253316/w896h680x64y0-7aaf931d.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) ### 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!!" CA $279 CA $591 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Highland-Hotels-Step-Into-History-Unwind-At-Spring-Apt-A-Charming-At-Theof-NYHudson-Valley.h90253316.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/220000/216900/216870/bc5eecd4.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) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/220000/216900/216870/7271a3ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus The Inn & Suites At The Falls Red Oaks Mill 7.6/10 Good (409) "Beautiful location and yummy breakfast" CA $134 CA $151 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Poughkeepsie-Hotels-Best-Western-Plus-The-Inn-Suites-At-The-Falls.h216870.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/910000/906700/906700/6fe2b40c.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) ![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 (1003) "Awesome staff, awesome stay!!" CA $94 CA $107 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Hyde-Park-Poughkeepsie-North.h906700.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) ![Lobby](https://images.trvl-media.com/lodging/100000000/99860000/99850800/99850733/w4000h2661x0y0-566be3f8.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) ![Meeting facility](https://images.trvl-media.com/lodging/100000000/99860000/99850800/99850733/634879ca.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 (404) "Nice rooms, a good restaurant on site " CA $244 CA $276 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Hyde-Park-Hotels-Inn-At-Bellefield-Hyde-Park.h99850733.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) ![Reception](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/3dad591c.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) ### Hampton Inn & Suites Poughkeepsie Crown Heights 8.6/10 Excellent (1006) "Excellent facility with great breakfast buffet." CA $159 CA $185 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information) ![Fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/2000000/1340000/1336000/1335929/4a7fc30b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1340000/1336000/1335929/c812852f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1340000/1336000/1335929/9eb47f6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1340000/1336000/1335929/6ceeff2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### HYATT house Fishkill/Poughkeepsie Fishkill 8.8/10 Excellent (1003) "Lovely property, convenient location, very comfortable hotel, nice breakfast. " CA $193 CA $219 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Poughkeepsie-Hotels-HYATT-House-FishkillPoughkeepsie.h1335929.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=2025-10-19&endDate=2025-10-20®ionId=115050&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## Top Highland Hotel Reviews ![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 "Very nice hotel " [](https://expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Hyde-Park-Poughkeepsie-North.h906700.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 "This place has one of the best showers! The water pressure is almost like getting power washed. My husband loved it! Convient to Main St Poughkeepsie for dining options." [](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 "T" [](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 "Friendly staff, clean rooms. Could use better seating." [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.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 "The room was spacious, clean, and comfortable. There is direct TV available for entertainment. Breakfast was nice. The presence of a pool and hot tub is great too. This hotel accepts dogs and cats 50 lbs and under with additional fee." [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information) ![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 "When it comes to a pleasant surprise, this was definitely IT! Clean, comfortable, inexpensive, friendly, renovated, and (did I mention) inexpensive!?? Adorable little breakfast area with complimentary breakfast foods as well. " [](https://expedia.ca/Poughkeepsie-Hotels-Americas-Best-Value-Inn-New-Paltz.h897882.Hotel-Information) ![Minnewaska Lodge](//images.trvl-media.com/lodging/2000000/1210000/1201800/1201707/3be04d40_y.jpg) ### Minnewaska Lodge 10/10 Excellent "Beautiful, the staff was amazing I called and said we were coming for my mom’s birthday and they put balloons in the room! " [](https://expedia.ca/Poughkeepsie-Hotels-Minnewaska-Lodge.h1201707.Hotel-Information) ![DoubleTree by Hilton Poughkeepsie Convention Center](//images.trvl-media.com/lodging/1000000/20000/14600/14563/acc87956_y.jpg) ### DoubleTree by Hilton Poughkeepsie Convention Center 10/10 Excellent "This hotel was wonderful. We attended a concert at the Civic Center and staying here was so convenient. Very clean, friendly staff, " [](https://expedia.ca/Poughkeepsie-Hotels-Poughkeepsie-Grand-Hotel.h14563.Hotel-Information) ![Quality Inn Poughkeepsie](//images.trvl-media.com/lodging/1000000/10000/6500/6465/a647c710_y.jpg) ### Quality Inn Poughkeepsie 10/10 Excellent "Really wonderful staff." [](https://expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Poughkeepsie.h6465.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. Roosevelt Presidential Library and Museum and Poughkeepsie Galleria. ## 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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