Title: Book the Best ROMANTIC Hotels in Middletown, NY from CA $133 - Middletown Romantic Getaways | Expedia.ca [Hotels in Middletown](https://expedia.ca/Middletown-Hotels.d8864.Travel-Guide-Hotels)[Vacation Rentals in Middletown](https://expedia.ca/Middletown-Vacation-Rentals.d8864.Travel-Guide-VacationRentals)[Flights to Middletown](https://expedia.ca/Cheap-Flights-To-Middletown.d8864.Travel-Guide-Flights)[Things to do in Middletown](https://expedia.ca/Things-To-Do-In-Middletown.d8864.Travel-Guide-Activities)[Middletown Car Rentals](https://expedia.ca/Car-Rentals-In-Middletown.d8864.Car-Rental-Guide)[Middletown Vacation Packages](https://expedia.ca/Middletown.d8864.Destination-Travel-Guides) ![Route 17 in ny is a great road to view the fall foliage](https://images.trvl-media.com/place/8005/8b2c54c4-af30-4521-9b56-3bdf0a8d1a15.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Vincent Ramundo ![](https://images.trvl-media.com/place/8005/8b2c54c4-af30-4521-9b56-3bdf0a8d1a15.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 availability on Middletown Romantic Hotels Tonight [Mar 1 - Mar 2](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2026-03-01&endDate=2026-03-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Mar 2 - Mar 3](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2026-03-02&endDate=2026-03-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2026-03-06&endDate=2026-03-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) In two weeks [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2026-03-13&endDate=2026-03-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Our top choices for Middletown romantic hotels ![View from property](https://images.trvl-media.com/lodging/49000000/48280000/48273100/48273068/21e70f22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/49000000/48280000/48273100/48273068/0da6fc7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/49000000/48280000/48273100/48273068/ccd2fb04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/49000000/48280000/48273100/48273068/ea96dde2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Inn by Marriott Middletown Goshen [](https://www.expedia.ca/Newburgh-Hotels-Residence-Inn-By-Marriott-Middletown-Goshen.h48273068.Hotel-Information) Middletown 9.4/10 Exceptional (322 reviews) "Always amazing was my second time here and will stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) CiCi CA $220 CA $259 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Newburgh-Hotels-Residence-Inn-By-Marriott-Middletown-Goshen.h48273068.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/16000000/15990000/15984700/15984645/3c35a288.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15990000/15984700/15984645/92beb582.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free self parking](https://images.trvl-media.com/lodging/16000000/15990000/15984700/15984645/27c83ba3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/16000000/15990000/15984700/15984645/74396b43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites by Hilton Middletown [](https://www.expedia.ca/Newburgh-Hotels-Home2-Suites-By-Hilton-Middletown.h15984645.Hotel-Information) Middletown 9.0/10 Wonderful (751 reviews) "Room is clean and spacious, staffs are friendly and professional, highly recommended!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rocky CA $233 CA $281 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Newburgh-Hotels-Home2-Suites-By-Hilton-Middletown.h15984645.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/30000/27300/27210/54a4e005.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/1000000/30000/27300/27210/ab56e4cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/27300/27210/5acfc319.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/27300/27210/95f0eb53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Hunt's Landing Hotel Matamoras/Milford [](https://www.expedia.ca/Matamoras-Hotels-Best-Western-Hunts-Landing-Hotel-MatamorasMilford.h27210.Hotel-Information) Matamoras 8.6/10 Excellent (1,002 reviews) "Very enjoyable stay. Room was clean and the bed was comfortable. The breakfast was also a nice perk. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica CA $122 CA $133 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Matamoras-Hotels-Best-Western-Hunts-Landing-Hotel-MatamorasMilford.h27210.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/679bdd4c.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) ![Lobby](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/13890846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Overlook Lodge at Bear Mountain [](https://www.expedia.ca/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 CA $140 CA $159 total includes taxes & fees Mar 31 - Apr 1 [](https://www.expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.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) ![Interior detail](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/20894557.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/00e54810.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/2154c327.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borland House Inn [](https://www.expedia.ca/Newburgh-Hotels-Borland-House-Inn.h11796055.Hotel-Information) Montgomery 9.2/10 Wonderful (153 reviews) "Breakfast was hot and tasty. Staff were all pleasant and accommodating. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) wendy [](https://www.expedia.ca/Newburgh-Hotels-Borland-House-Inn.h11796055.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/101000000/101000000/100997000/100996967/6aaba293.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) ### The Alder at Resorts World Catskills [](https://www.expedia.ca/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 [](https://www.expedia.ca/Monticello-Hotels-The-Alder-At-Resorts-World-Catskills.h100996967.Hotel-Information) ![Resort view](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/0479130a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/d1a6e271.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 7 AM to 10 PM, free cabanas, sun loungers](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/95ef3af1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Food and drink](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/d6b9765c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Resorts World Catskills Casino [](https://www.expedia.ca/Monticello-Hotels-Resorts-World-Catskills-Casino.h23970267.Hotel-Information) Monticello 8.6/10 Excellent (1,078 reviews) "Yessss the hotel was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelvin [](https://www.expedia.ca/Monticello-Hotels-Resorts-World-Catskills-Casino.h23970267.Hotel-Information) ![Outdoor wedding area](https://images.trvl-media.com/lodging/110000000/109920000/109911700/109911634/b0d46466.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/110000000/109920000/109911700/109911634/6aefbcd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/110000000/109920000/109911700/109911634/8d973ad2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/110000000/109920000/109911700/109911634/593a0f58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### John H Wallace House [](https://www.expedia.ca/Milford-Hotels-John-H-Wallace-House.h109911634.Hotel-Information) Milford 10/10 Exceptional (15 reviews) "The John H. Wallace House is a welcoming and comfortable place to stay. Don’t hesitate to make a reservation to go there. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara CA $236 CA $258 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Milford-Hotels-John-H-Wallace-House.h109911634.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/111000000/110800000/110798400/110798378/a9ea5c03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/111000000/110800000/110798400/110798378/9e133beb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/111000000/110800000/110798400/110798378/cc3411cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/111000000/110800000/110798400/110798378/78872596.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Verde BB Greenwood Lake NY [](https://www.expedia.ca/Monroe-Hotels-Villa-Verde-BB-Greenwood-Lake-NY.h110798378.Hotel-Information) Monroe 10/10 Exceptional (16 reviews) "Excellent stay and delicious breakfast. Clear communication!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda CA $251 CA $284 total includes taxes & fees Mar 9 - Mar 10 [](https://www.expedia.ca/Monroe-Hotels-Villa-Verde-BB-Greenwood-Lake-NY.h110798378.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/6000000/5800000/5792300/5792279/74c2079f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/6000000/5800000/5792300/5792279/379d3719.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/6000000/5800000/5792300/5792279/dbbc3fc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/6000000/5800000/5792300/5792279/a36b2487.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Thayer Hotel at West Point [](https://www.expedia.ca/Newburgh-Hotels-Thayer-Hotel.h5792279.Hotel-Information) West Point 9.0/10 Wonderful (694 reviews) "Beautiful architecture, friendly and profesional staff. Great dinning at MacArthur’s Riverview. Convenient and accesible for those visiting USMA." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sandra M CA $244 CA $312 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Newburgh-Hotels-Thayer-Hotel.h5792279.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=2026-03-16&endDate=2026-03-17®ionId=8864&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ![](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.ca/deals?rfrr=AFFINITY_SPRING_PROMO_8864) ## Top Middletown Hotel Reviews ![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 "Excellent stay! " [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Mountain Creek](https://images.trvl-media.com/lodging/3000000/2900000/2899900/2899900/f09dc021_y.jpg) ### Mountain Creek 10/10 Excellent "Great spacious room. service of staff was wonderful and ski on ski off is priceless " [](https://expedia.ca/Vernon-Hotels-Mountain-Creek.h2899900.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in Middletown? ### When is the best time of year for a romantic getaway to Middletown? ### What is there to do in Middletown? ### What's the best way to get to Middletown and around town during my romantic getaway? ## Explore a world of travel with Expedia - Lodging - More ways to book - [Cheap Hotels in Bloomingburg ](https://www.expedia.ca/Bloomingburg-Hotels-Cheap-Hotels.0-0-d3000448043-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Bloomingburg ](https://www.expedia.ca/Bloomingburg-Hotels-Hotel-With-Pool.0-0-d3000448043-tHotelwithPool.Travel-Guide-Filter-Hotels) - 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