Title: Book the Best Montgomery Hotels with FREE WIFI in 2025 | Expedia.ca [Hotels in Montgomery](https://expedia.ca/Montgomery-Hotels.d8728.Travel-Guide-Hotels)[Vacation Rentals in Montgomery](https://expedia.ca/Montgomery-Vacation-Rentals.d8728.Travel-Guide-VacationRentals)[Things to do in Montgomery](https://expedia.ca/Things-To-Do-In-Montgomery.d8728.Travel-Guide-Activities)[Montgomery Car Rentals](https://expedia.ca/Car-Rentals-In-Montgomery.d8728.Car-Rental-Guide)[Montgomery Vacation Packages](https://expedia.ca/Montgomery.d8728.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/7258650cf3c9c107b2e4d18aa267cfe2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by ViajandoconAna Rustrian # Find Hotels with Wifi in Montgomery, NY from CA $133 ![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 Montgomery Hotels with Wifi Tonight [Oct 7 - Oct 8](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2025-10-07&endDate=2025-10-08&adults=2&amenities=WIFI&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 8 - Oct 9](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2025-10-08&endDate=2025-10-09&adults=2&amenities=WIFI&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=WIFI&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=WIFI&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Montgomery Hotels with Wifi ![Exterior](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/98944f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/fe354234.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/f3b7bb7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/dc5981dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Montgomery by IHG Montgomery 8.8/10 Excellent (767) "We really like the hotel and area very safe" CA $139 CA $163 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Suites-Montgomery.h7814618.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) ![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) ![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) ![View from property](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/25051ab3.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 8 - Oct 9 [](https://www.expedia.ca/Newburgh-Hotels-Borland-House-Inn.h11796055.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/117000000/116370000/116362400/116362325/60f2c951.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116370000/116362400/116362325/a4cc8a05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116370000/116362400/116362325/77fcc776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116370000/116362400/116362325/1522d348.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit Montgomery 10/10 Exceptional (1) "Guido was very responsive and thoughtful! My partner and I stayed with our small dog and it was safe, clean, well stocked and in a beautiful area. Highly recommend to those looking to stay in the area!" CA $211 CA $335 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Montgomery-Hotels-Cozy-Cabin-Gateway-I-15-Acres-W-Pool-Firepit.h116362325.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113870000/113869800/113869761/13e7998f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/114000000/113870000/113869800/113869761/4053b21a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/114000000/113870000/113869800/113869761/880dfe07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113870000/113869800/113869761/2b65d387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serene and modern Woodland Retreat, Hudson Valley & Catskills Montgomery 10/10 Exceptional (2) "We stayed the weekend for our daughter’s wedding. Property was as pictured and very clean. Kitchen was well stocked with everything you may need. Monica was very helpful and check in was easy process. She answered messages quickly. The town of Montgomery was nearby and very nice. Also great proximity to several apple and cider places. Very pretty area." CA $390 CA $699 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Montgomery-Hotels-Serene-And-Modern-Woodland-Retreat.h113869761.Hotel-Information) ![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/860000/855600/855538/7ac7ec53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/855600/855538/78c409cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/860000/855600/855538/c21f4b9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/855600/855538/2c45805f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Montgomery Maybrook Montgomery 6.4/10 (1003) "The hotel needs a major makeover " CA $117 CA $133 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Newburgh-Hotels-Super-8-By-Wyndham-Montgomery-Maybrook.h855538.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99760000/99751300/99751209/7ce217c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99760000/99751300/99751209/33d9a952.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/100000000/99760000/99751300/99751209/26c38d83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, table tennis](https://images.trvl-media.com/lodging/100000000/99760000/99751300/99751209/511279ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Farmhouse-Hot Tub, King Beds, Game Room & View Montgomery 10/10 Exceptional (15) "We loved our stay here! The property is gorgeous and the hosts were helpful and communicative. The house was clean and had everything we needed." CA $739 CA $1,464 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Montgomery-Hotels-Dream-Escape.h99751209.Hotel-Information) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/105000000/104270000/104260900/104260808/127e9816.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/105000000/104270000/104260900/104260808/78f4c900.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video library](https://images.trvl-media.com/lodging/105000000/104270000/104260900/104260808/ac2ddafa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104270000/104260900/104260808/84075d3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking. Montgomery 10/10 Exceptional (2) "Location was fantastic - short short walk (100-300’) to a handful of very good restaurants. The apartment is brand new, extraordinarily clean, well provisioned and has everything you could possibly need. It’s clear that the owners take pride in their property and take care of it accordingly. They are also super responsive and helpful. I accidentally locked myself out of the apartment one morning and " CA $204 CA $433 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Montgomery-Hotels-Luxury-New-1BR-950-Sq-Ft-Apartment-Sleeps-4-Stocked-Kitchen.h104260808.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/105000000/104970000/104965400/104965399/feb0c593.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee and/or coffee maker](https://images.trvl-media.com/lodging/105000000/104970000/104965400/104965399/c01759b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/105000000/104970000/104965400/104965399/d8180870.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/105000000/104970000/104965400/104965399/3424405a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Hudson Valley Apt 202 - King/Queen/Twin Montgomery 9.8/10 Exceptional (12) "Such a cute apartment and very clean. Everything is new and the town is very quaint!! Close to other things like shopping and restaurants. Definitely would stay again and recommend to anyone looking for a clean, quiet and safe area to stay." CA $212 CA $395 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Montgomery-Hotels-Modern-Hudson-Valley-Apt-202-KingQueenTwin.h104965399.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/02f3df9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/1a5890e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/09941fc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/309e00bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Chester by IHG Chester 8.4/10 Very good (1005) "Friendly and accommodating staff. " CA $161 CA $190 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/c7d384a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/9631af0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/da52c924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/903ceccc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Harriman Woodbury Central Valley 9.2/10 Wonderful (1007) "Great place to stay, very clean and conveniently located" CA $165 CA $203 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.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=2025-10-21&endDate=2025-10-22®ionId=8728&adults=2&amenities=WIFI&sort=RECOMMENDED&openPlayBack=true) ## Top Montgomery Hotel Reviews ![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 "Spacious Bathroom " [](https://expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Suites-Fishkill-South-Near-I-84.h1766609.Hotel-Information) ![Hampton Inn Harriman Woodbury](//images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/c7d384a9_y.jpg) ### Hampton Inn Harriman Woodbury 10/10 Excellent "Found this hotel last year, it is super convenient for getting to the NY ren faire and has a Popeye's just up the driveway plus a whole shopping complex but you would never know when you are at the hotel. It is tucked all the way in the back and is nice & quiet. " [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.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 very large and the price was great." [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information) ![Overlook Lodge at Bear Mountain](//images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6_y.jpg) ### Overlook Lodge at Bear Mountain 10/10 Excellent "Incredibly peaceful when walking in the forest. Swimming in the lake and stream was amazing " [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.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 stay. Nothing really special about the place except the breakfast which had more choices than usual." [](https://expedia.ca/Poughkeepsie-Hotels-Holiday-Inn-Express-Poughkeepsie.h12157.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 "Lovely clean spacious room with beautiful view of the Hudson River and its bridges. Friendly welcoming staff." [](https://expedia.ca/Poughkeepsie-Hotels-Poughkeepsie-Grand-Hotel.h14563.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 "Hotel and Room was very clean. " [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.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 "Room was very clean but a little worn. Bed and linens were comfortable. Bathroom was clean. Very quiet. Staff were very welcoming, polite and accommodating. 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