Title: Montgomery Cottages from CA $259 | 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) ![Montgomery is a town in Orange County, New York, United States. The population was 22,606 at the 2010 census. It was named in honor of Richard Montgomery, an American Revolutionary War general killed in 1775 at the Battle of Quebec. The Town of Montgomery is in the northern part of the county at the county line shared by Ulster County. Montgomery is immediately west of the Town of Newburgh. It contains three villages, one also called Montgomery, as well as Walden and most of Maybrook.](https://images.trvl-media.com/place/8728/d5b50f96-b364-4937-ab55-555e72199f5b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by ViajandoconAna Rustrian ![](https://images.trvl-media.com/place/8728/d5b50f96-b364-4937-ab55-555e72199f5b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 prices for these dates In two weeks [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=8728&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Montgomery cottages ![Smart TV](https://images.trvl-media.com/lodging/79000000/78140000/78138100/78138015/dd263f18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/79000000/78140000/78138100/78138015/eb48d384.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78140000/78138100/78138015/54004000.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78140000/78138100/78138015/3008d822.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relaxing Farm Cottage Escape, 10 Min from LEGOLAND [](https://www.expedia.ca/Goshen-Hotels-Relaxing-Farm-Cottage-Escape.h78138015.Hotel-Information) Goshen 9.8/10 Exceptional (13 reviews) "Beautiful location. We really enjoyed seeing the deer in the field every morning. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aaron M. CA $203 CA $405 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Goshen-Hotels-Relaxing-Farm-Cottage-Escape.h78138015.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/dabdeda4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/7cf93160.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace, books](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/4fbee988.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace, books](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/cd189b6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks [](https://www.expedia.ca/Kerhonkson-Hotels-Dream-Cottage-In-The-Gunks.h83439008.Hotel-Information) Kerhonkson 9.4/10 Exceptional (12 reviews) "Charming and relaxing cottage. Perfect location for hiking or enjoying Lake Minnewaska or Mohonk Preserve. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patrick S. CA $109 CA $259 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Kerhonkson-Hotels-Dream-Cottage-In-The-Gunks.h83439008.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/3a9ea66f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/e56d490f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/5ed95c10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/dfec5e09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands [](https://www.expedia.ca/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information) Fort Montgomery 9.8/10 Exceptional (131 reviews) "It has an incredible mountain and water view. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MIHYUN CA $258 CA $420 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.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=2026-02-07&endDate=2026-02-08®ionId=8728&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Montgomery%2C+New+York%2C+United+States+of+America®ionId=8728&latLong=41.527596%2C-74.236816&adults=2&startDate=2026-04-24&d1=2026-04-24&endDate=2026-04-27&d2=2026-04-27&lodging=CABIN) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Montgomery%2C+New+York%2C+United+States+of+America®ionId=8728&latLong=41.527596%2C-74.236816&adults=2&startDate=2026-04-24&d1=2026-04-24&endDate=2026-04-27&d2=2026-04-27&lodging=APARTMENT) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Montgomery%2C+New+York%2C+United+States+of+America®ionId=8728&latLong=41.527596%2C-74.236816&adults=2&startDate=2026-04-24&d1=2026-04-24&endDate=2026-04-27&d2=2026-04-27&lodging=VACATION_HOME) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Montgomery%2C+New+York%2C+United+States+of+America®ionId=8728&latLong=41.527596%2C-74.236816&adults=2&startDate=2026-04-24&d1=2026-04-24&endDate=2026-04-27&d2=2026-04-27&lodging=COTTAGE) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Montgomery%2C+New+York%2C+United+States+of+America®ionId=8728&latLong=41.527596%2C-74.236816&adults=2&startDate=2026-04-24&d1=2026-04-24&endDate=2026-04-27&d2=2026-04-27&lodging=APART_HOTEL) Villas [](https://www.expedia.ca/Hotel-Search?destination=Montgomery%2C+New+York%2C+United+States+of+America®ionId=8728&latLong=41.527596%2C-74.236816&adults=2&startDate=2026-04-24&d1=2026-04-24&endDate=2026-04-27&d2=2026-04-27&lodging=VILLA) Condos [](https://www.expedia.ca/Hotel-Search?destination=Montgomery%2C+New+York%2C+United+States+of+America®ionId=8728&latLong=41.527596%2C-74.236816&adults=2&startDate=2026-04-24&d1=2026-04-24&endDate=2026-04-27&d2=2026-04-27&lodging=CONDO) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Montgomery%2C+New+York%2C+United+States+of+America®ionId=8728&latLong=41.527596%2C-74.236816&adults=2&startDate=2026-04-24&d1=2026-04-24&endDate=2026-04-27&d2=2026-04-27&lodging=CHALET) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FMontgomery-Cottages.d8728-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FMontgomery-Cottages.d8728-aaCottages.Travel-Guide-Accommodation) ## Top Montgomery Hotel Reviews ![Hampton Inn by Hilton New Paltz](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/bd59d6cb_y.jpg) ### Hampton Inn by Hilton New Paltz 10/10 Excellent "Super clean and new. Breakfast was great, turkey sausage, good fluffy eggs, etc." [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information) ![Resorts World Catskills Casino](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/ecb80f49_y.jpg) ### Resorts World Catskills Casino 10/10 Excellent "Yessss the hotel was great" [](https://expedia.ca/Monticello-Hotels-Resorts-World-Catskills-Casino.h23970267.Hotel-Information) ![Overlook Lodge at Bear Mountain](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6_y.jpg) ### Overlook Lodge at Bear Mountain 10/10 Excellent "Great staff. I will be back soon. I wanted to hike but couldn’t find were to access because the construction " [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![The Kartrite Resort & Indoor Waterpark](https://images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/90ceac4d_y.jpg) ### The Kartrite Resort & Indoor Waterpark 10/10 Excellent "Great place kids loved it " [](https://expedia.ca/Monticello-Hotels-The-Kartrite-Resort-Indoor-Waterpark.h31681637.Hotel-Information) ![Sleep Inn & Suites Middletown - Goshen](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/1b0779e7_y.jpg) ### Sleep Inn & Suites Middletown - Goshen 10/10 Excellent "Yes" [](https://expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) ![Hampton Inn & Suites Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/47fa2e85_y.jpg) ### Hampton Inn & Suites Poughkeepsie 10/10 Excellent "Relaxing" [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.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 "Friendly staff and updated & very clean room" [](https://expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information) ![Borland House Inn](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/47637293_y.jpg) ### Borland House Inn 10/10 Excellent "Breakfast was hot and tasty. Staff were all pleasant and accommodating. " [](https://expedia.ca/Newburgh-Hotels-Borland-House-Inn.h11796055.Hotel-Information) ![Sleep Inn & Suites Monroe - Woodbury](https://images.trvl-media.com/lodging/21000000/20600000/20597600/20597588/0db56af9_y.jpg) ### Sleep Inn & Suites Monroe - Woodbury 10/10 Excellent "Staff was friendly and helpful. Room was clean and breakfast was a nice perk " [](https://expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Monroe-Woodbury.h20597588.Hotel-Information) ## Find out more about Montgomery ## Montgomery Cottages information | Number of reviews | 137 | | ----------------- | ------------ | | Accommodation | 102 Cottages | | Lowest Price | CA $259 | | Highest Price | CA $420 | ## Frequently asked questions ### Why book your cottage in Montgomery with Expedia? ### How can I find cheap cottages in Montgomery? ### What is there to do in Montgomery near my cottage? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [2 Star Hotels in Walden ](https://www.expedia.ca/2Star-Walden-Hotels.s20-0-d6361117.Travel-Guide-Filter-Hotels) - [Hotels near Angry Orchard ](https://www.expedia.ca/Angry-Orchard-Hotels.0-l553248635998039554-0.Travel-Guide-Filter-Hotels) - [Hotels near Brotherhood Winery ](https://www.expedia.ca/Brotherhood-Winery-Hotels.0-l6171741-0.Travel-Guide-Filter-Hotels) - 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