Title: The Best Hotels with a Pool in Montgomery from $102 in 2026 | Expedia.com [Montgomery Travel Guide](https://expedia.com/Montgomery.dx8728)[Hotels in Montgomery](https://expedia.com/Montgomery-Hotels.d8728.Travel-Guide-Hotels)[Vacation Rentals in Montgomery](https://expedia.com/Montgomery-Vacation-Rentals.d8728.Travel-Guide-VacationRentals)[Flights to Montgomery](https://expedia.com/Cheap-Flights-To-Montgomery.d8728.Travel-Guide-Flights)[Things to do in Montgomery](https://expedia.com/Things-To-Do-In-Montgomery.d8728.Travel-Guide-Activities)[Car Rentals in Montgomery](https://expedia.com/Car-Rentals-In-Montgomery.d8728.Car-Rental-Guide)[Montgomery Vacation Packages](https://expedia.com/Montgomery.d8728.Destination-Travel-Guides) ![Autumn foliage in the Mohawk Valley, Montgomery County, New York State, USA.](https://images.trvl-media.com/place/8728/e92a028d-f2c6-4a41-a280-7692010fed7a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/8728/e92a028d-f2c6-4a41-a280-7692010fed7a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![](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 a Pool Tonight [Mar 5 - Mar 6](https://www.expedia.com/Hotel-Search?regionId=8728&startDate=2026-03-05&endDate=2026-03-06&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 6 - Mar 7](https://www.expedia.com/Hotel-Search?regionId=8728&startDate=2026-03-06&endDate=2026-03-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=8728&startDate=2026-03-06&endDate=2026-03-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=8728&startDate=2026-03-13&endDate=2026-03-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Montgomery hotels with a pool ![Exterior](https://images.trvl-media.com/lodging/117000000/116370000/116362400/116362325/e25829b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116370000/116362400/116362325/1ae526bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/117000000/116370000/116362400/116362325/1616e5db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116370000/116362400/116362325/8d663c7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Cabin with Pool & Fire Pit [](https://www.expedia.com/Montgomery-Hotels-Cozy-Cabin-Gateway-I-15-Acres-W-Pool-Firepit.h116362325.Hotel-Information) Montgomery 10/10 Exceptional (3 reviews) "This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah A. $182 nightly $205 total Mar 9 - Mar 10 Total with taxes and fees [](https://www.expedia.com/Montgomery-Hotels-Cozy-Cabin-Gateway-I-15-Acres-W-Pool-Firepit.h116362325.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/a79c4292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/618cd435.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/80e497ec.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) ### Hampton Inn & Suites Poughkeepsie [](https://www.expedia.com/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information) Crown Heights 9.0/10 Wonderful (1,008 reviews) "Best staff ever great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rafael $95 nightly $111 total Mar 14 - Mar 15 Total with taxes and fees [](https://www.expedia.com/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/383ffb6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/8626bd92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/7384700a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/13890846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Overlook Lodge at Bear Mountain [](https://www.expedia.com/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) Bear Mountain 8.4/10 Very Good (1,003 reviews) "The stone lodges are cute and cozy and the staff were quick and helpful if you needed anything. Great for a short stay at a reasonable price." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Judith $100 nightly $114 total Mar 12 - Mar 13 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/fb63b6d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/5a64b5a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/0bd48f86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/ba2c672f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Middletown Goshen [](https://www.expedia.com/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information) Middletown 8.6/10 Excellent (1,003 reviews) "Love staying here " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) devin $101 nightly $119 total Mar 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/64788546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/2d8c93f7.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/2000000/1200000/1194400/1194365/308be1ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Chester by IHG [](https://www.expedia.com/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) Chester 8.6/10 Excellent (1,004 reviews) "great stay. had everything needed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dana $86 nightly $102 total Mar 8 - Mar 9 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/e02a568f.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/3b6f022d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/f4de9a4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Fishkill [](https://www.expedia.com/Poughkeepsie-Hotels-Hilton-Garden-Inn-Fishkill.h890436.Hotel-Information) Fishkill 8.6/10 Excellent (1,001 reviews) "Room was beautifully spotless. Enjoyed everything during my stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Francine $98 nightly $110 total Mar 12 - Mar 13 Total with taxes and fees [](https://www.expedia.com/Poughkeepsie-Hotels-Hilton-Garden-Inn-Fishkill.h890436.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1220000/1214400/1214332/d2d7994a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1220000/1214400/1214332/5b25316b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1220000/1214400/1214332/w4000h2662x0y0-aa463bc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/2000000/1220000/1214400/1214332/53a095c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Goshen Middletown [](https://www.expedia.com/Newburgh-Hotels-Fairfield-Inn-Suites-By-Marriott-Goshen-Middletown.h1214332.Hotel-Information) Goshen 8.8/10 Excellent (1,001 reviews) "Was nice place to stay I like it " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Artemio $93 nightly $114 total Mar 12 - Mar 13 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Fairfield-Inn-Suites-By-Marriott-Goshen-Middletown.h1214332.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/101000000/101000000/100997000/100996967/1bc406d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/101000000/101000000/100997000/100996967/bd1fd61c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/101000000/100997000/100996967/6aaba293.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, sauna, steam room, body treatments](https://images.trvl-media.com/lodging/101000000/101000000/100997000/100996967/af635e5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Alder at Resorts World Catskills [](https://www.expedia.com/Monticello-Hotels-The-Alder-At-Resorts-World-Catskills.h100996967.Hotel-Information) Monticello 8.2/10 Very Good (211 reviews) "GREAT SPOT" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rolan $153 nightly $172 total Mar 12 - Mar 13 Total with taxes and fees [](https://www.expedia.com/Monticello-Hotels-The-Alder-At-Resorts-World-Catskills.h100996967.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) ![Restaurant](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/00367844.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/7df797b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn by Hilton New Paltz [](https://www.expedia.com/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information) New Paltz 9.4/10 Exceptional (1,011 reviews) "Spotless room, Amazing staff. Will be booking at this location when i am in the area. Great access to stores and amentities nearby, great town New Paltz!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jake $122 nightly $137 total Mar 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/38c7288e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Accessible, Non Smoking | Desk, iron/ironing board, free cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/38401260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/cabaefdf.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 [](https://www.expedia.com/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) New Windsor 8.4/10 Very Good (1,005 reviews) "Superb place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Denessy $99 nightly $112 total Mar 8 - Mar 9 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.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.com/Hotel-Search?startDate=2026-03-19&endDate=2026-03-20®ionId=8728&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Montgomery Breakfast included Hot tub 4 stars 5 stars Spa ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=AFFINITY_SPRING_PROMO_8728) ## Top Montgomery Hotel Reviews ![Hampton Inn Harriman Woodbury](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/e0fcb0f3_y.jpg) ### Hampton Inn Harriman Woodbury 6/10 Okay "Needs to be updated " [](https://expedia.com/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![Courtyard by Marriott Middletown Goshen](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/5a64b5a6_y.jpg) ### Courtyard by Marriott Middletown Goshen 10/10 Excellent "Everything was great " [](https://expedia.com/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information) ![Sleep Inn & Suites Middletown - Goshen](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/aeade474_y.jpg) ### Sleep Inn & Suites Middletown - Goshen 8/10 Good "The tvs are pretty outdated. Wish it at least had Netflix. But overall the room was clean and not a bad spot to stay if you need to chill for a night or two. Gets the job done. Breakfast options were kinda limited but at least the offer it complimentary." [](https://expedia.com/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) ![Holiday Inn Express & Suites Montgomery by IHG](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/605b2de6_y.jpg) ### Holiday Inn Express & Suites Montgomery by IHG 10/10 Excellent "It was great" [](https://expedia.com/Newburgh-Hotels-Holiday-Inn-Express-Suites-Montgomery.h7814618.Hotel-Information) ![Hampton Inn by Hilton New Paltz](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/dab27d3b_y.jpg) ### Hampton Inn by Hilton New Paltz 10/10 Excellent "Room was spacious and clean. Bed was very very comfortable. The breakfast was great. Will definitely stay again!" [](https://expedia.com/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information) ![Holiday Inn Express Fishkill-Mid Hudson Valley by IHG](https://images.trvl-media.com/lodging/2000000/1690000/1680400/1680342/830db074_y.jpg) ### Holiday Inn Express Fishkill-Mid Hudson Valley by IHG 10/10 Excellent "Modern and clean. Coffee available 24 hours. Decent breakfast. " [](https://expedia.com/Poughkeepsie-Hotels-Holiday-Inn-Express-Fishkill-Mid-Hudson-Valley.h1680342.Hotel-Information) ![Courtyard by Marriott Fishkill](https://images.trvl-media.com/lodging/1000000/20000/17300/17286/3f9cb655_y.jpg) ### Courtyard by Marriott Fishkill 10/10 Excellent "The room was clean and the staff was very helpful . " [](https://expedia.com/Poughkeepsie-Hotels-Courtyard-By-Marriott-Fishkill.h17286.Hotel-Information) ![Hampton Inn & Suites Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/47fa2e85_y.jpg) ### Hampton Inn & Suites Poughkeepsie 6/10 Okay "Free breakfast ends early, food was cold and mediocre. Rooms were big but old and smelled musty. Pool was tiny, looked nice in the picture" [](https://expedia.com/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 8/10 Good "Internet was fine. Staff was very helpful. " [](https://expedia.com/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Montgomery? ### What is there to see and do in Montgomery? ### When is the best time to book a hotel with a pool in Montgomery? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [New York Hotels ](https://www.expedia.com/New-York-Hotels.d178293.Travel-Guide-Hotels) - [Hotels near Orange County ](https://www.expedia.com/Orange-County-Airport-Hotels.0-aMGJ-0.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in Walden ](https://www.expedia.com/Walden-Hotels-Hotels-With-Free-Parking.0-0-d6361117-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Walden ](https://www.expedia.com/Walden-Hotels-Luxury-Hotel.0-0-d6361117-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Historic Hotels in Walden ](https://www.expedia.com/Walden-Hotels-Historic-Hotel.0-0-d6361117-tHistoricHotel.Travel-Guide-Filter-Hotels) - 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