Title: Book the Best ROMANTIC Hotels in Middletown, NY from CA $138 - 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 [Jan 15 - Jan 16](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2026-01-15&endDate=2026-01-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Jan 16 - Jan 17](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2026-01-16&endDate=2026-01-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2026-01-16&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Our top choices for Middletown romantic hotels ![Courtyard](https://images.trvl-media.com/lodging/16000000/15990000/15984700/15984645/3c35a288.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) ![Lobby](https://images.trvl-media.com/lodging/16000000/15990000/15984700/15984645/e39f1f2f.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 (749 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 $229 CA $275 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Newburgh-Hotels-Home2-Suites-By-Hilton-Middletown.h15984645.Hotel-Information) ![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) ![View from property](https://images.trvl-media.com/lodging/49000000/48280000/48273100/48273068/9a478c40.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) ![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 (319 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 $223 CA $264 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Newburgh-Hotels-Residence-Inn-By-Marriott-Middletown-Goshen.h48273068.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) ![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) ![Lounge](https://images.trvl-media.com/lodging/1000000/30000/27300/27210/ab56e4cd.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 8.4/10 Very good (1,001 reviews) "The staff were great, nice lobby, clean rooms. Only downsides were the bathrooms haven’t been updated in many years, and the breakfast was subpar. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Olivia CA $126 CA $138 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Matamoras-Hotels-Best-Western-Hunts-Landing-Hotel-MatamorasMilford.h27210.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) ![6 bars/lounges](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/90312aff.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 (1,116 reviews) "Great resort hotel. Clean and big enough room, and nice people." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Youngkyu CA $199 CA $259 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Monticello-Hotels-Resorts-World-Catskills-Casino.h23970267.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6.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) ![Reception](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/679bdd4c.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) ### 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 (1,001 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 $136 CA $154 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.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/6000000/5800000/5792300/5792279/90389be1.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 (681 reviews) "Location was great & staying at a historic hotel was delightful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bobby CA $176 CA $236 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Newburgh-Hotels-Thayer-Hotel.h5792279.Hotel-Information) ![Water park](https://images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/7b139e0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/w966h620x25y37-6819803f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/f997ece6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges, poolside bar](https://images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/e6e1e949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Kartrite Resort & Indoor Waterpark [](https://www.expedia.ca/Monticello-Hotels-The-Kartrite-Resort-Indoor-Waterpark.h31681637.Hotel-Information) Monticello 8.2/10 Very good (1,913 reviews) "Everything was perfect, great hotel with indoor waterpark." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angel Antonio CA $211 CA $332 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Monticello-Hotels-The-Kartrite-Resort-Indoor-Waterpark.h31681637.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) ![7 bars/lounges](https://images.trvl-media.com/lodging/101000000/101000000/100997000/100996967/9db559da.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 (209 reviews) "Always a good time at this place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Precilla [](https://www.expedia.ca/Monticello-Hotels-The-Alder-At-Resorts-World-Catskills.h100996967.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) ![Lobby](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/2154c327.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) ### Borland House Inn [](https://www.expedia.ca/Newburgh-Hotels-Borland-House-Inn.h11796055.Hotel-Information) Montgomery 9.2/10 Wonderful (146 reviews) "Had a great stay at the the Borland House Inn a historical setting in a cute town with wonderful staff and a delicious breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah [](https://www.expedia.ca/Newburgh-Hotels-Borland-House-Inn.h11796055.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/80000000/79880000/79873100/79873064/2028d4aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ridge Suite](https://images.trvl-media.com/lodging/80000000/79880000/79873100/79873064/3e2f5ec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, pool views ](https://images.trvl-media.com/lodging/80000000/79880000/79873100/79873064/b47258f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, sauna, hot tub, body treatments, aromatherapy](https://images.trvl-media.com/lodging/80000000/79880000/79873100/79873064/09494c77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wildflower Farms, Auberge Collection [](https://www.expedia.ca/Gardiner-Hotels-Wildflower-Farms.h79873064.Hotel-Information) Gardiner 9.4/10 Exceptional (60 reviews) "Everything was ok, except for the fact that we couldn’t do late check out or that we payed a bit more for a standard room. But everything else was perfect " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sandra N CA $1,465 CA $1,701 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Gardiner-Hotels-Wildflower-Farms.h79873064.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=2026-01-30&endDate=2026-01-31®ionId=8864&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Middletown Hotel Reviews ![Mountain Creek](https://images.trvl-media.com/lodging/3000000/2900000/2899900/2899900/f09dc021_y.jpg) ### Mountain Creek 10/10 Excellent "easy check-in/check-out" [](https://expedia.ca/Vernon-Hotels-Mountain-Creek.h2899900.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 "Cozy and quiet. Rooms need size. Surroundings idellic. Nature abounds." [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Best Western Hunt's Landing Hotel Matamoras/Milford](https://images.trvl-media.com/lodging/1000000/30000/27300/27210/5acfc319_y.jpg) ### Best Western Hunt's Landing Hotel Matamoras/Milford 10/10 Excellent "Room was excellent " [](https://expedia.ca/Matamoras-Hotels-Best-Western-Hunts-Landing-Hotel-MatamorasMilford.h27210.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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