Title: Middletown, NY Villas Rentals | Expedia.com [Middletown Travel Guide](https://expedia.com/Middletown.dx8864)[Hotels in Middletown](https://expedia.com/Middletown-Hotels.d8864.Travel-Guide-Hotels)[Vacation Rentals in Middletown](https://expedia.com/Middletown-Vacation-Rentals.d8864.Travel-Guide-VacationRentals)[Flights to Middletown](https://expedia.com/Cheap-Flights-To-Middletown.d8864.Travel-Guide-Flights)[Things to do in Middletown](https://expedia.com/Things-To-Do-In-Middletown.d8864.Travel-Guide-Activities)[Car Rentals in Middletown](https://expedia.com/Car-Rentals-In-Middletown.d8864.Car-Rental-Guide)[Middletown Vacation Packages](https://expedia.com/Middletown.d8864.Destination-Travel-Guides) ![](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_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=8864&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 two months [May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=8864&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=8864&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 24 - Jul 26](https://www.expedia.com/Hotel-Search?regionId=8864&startDate=2026-07-24&endDate=2026-07-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Middletown villas ![Property grounds](https://images.trvl-media.com/lodging/77000000/76010000/76007300/76007287/578a66aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76010000/76007300/76007287/d06f6457.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, table tennis](https://images.trvl-media.com/lodging/77000000/76010000/76007300/76007287/20538ed5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, table tennis](https://images.trvl-media.com/lodging/77000000/76010000/76007300/76007287/80caa095.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury School House Retreat With Sauna & Pool- 1HR from NYC [](https://www.expedia.com/New-Hampton-Hotels-Luxury-School-House-Wheated-Pool-1HR-From-NYC.h76007287.Hotel-Information) New Hampton 10/10 Exceptional (19 reviews) "House was great, conveniently located to ski mountain, Hunter was a pleasure to work with, house was clean and had so many amenities for our family! Highly recommend! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer P. $1,142 nightly $1,349 total Apr 7 - Apr 8 Total with taxes and fees [](https://www.expedia.com/New-Hampton-Hotels-Luxury-School-House-Wheated-Pool-1HR-From-NYC.h76007287.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=2026-04-19&endDate=2026-04-20®ionId=8864&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.com/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America®ionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&lodging=CABIN) Cottages [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America®ionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&lodging=COTTAGE) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America®ionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&lodging=VACATION_HOME) Condos [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America®ionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&lodging=CONDO) Villas [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America®ionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&lodging=VILLA) Apartments [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America®ionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&lodging=APARTMENT) Chalets [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America®ionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&lodging=CHALET) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America®ionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&lodging=APART_HOTEL) ![](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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FMiddletown-Villas.d8864-aaVillas.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FMiddletown-Villas.d8864-aaVillas.Travel-Guide-Accommodation) ## Top Middletown Hotel Reviews ![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/38c7288e_y.jpg) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point 10/10 Excellent "U" [](https://expedia.com/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![The Kartrite Resort & Indoor Waterpark](https://images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/7b139e0a_y.jpg) ### The Kartrite Resort & Indoor Waterpark 8/10 Good "The waterpark was great. A great deal of seating, lifeguards were personable and alert. The room was clean and set up very well for our needs. " [](https://expedia.com/Monticello-Hotels-The-Kartrite-Resort-Indoor-Waterpark.h31681637.Hotel-Information) ![Holiday Inn Express Hotel & Suites Chester by IHG](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/8648b91b_y.jpg) ### Holiday Inn Express Hotel & Suites Chester by IHG 10/10 Excellent "yes parking was good and breakfast was plentiful" [](https://expedia.com/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) ![Hampton Inn Harriman Woodbury](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/e0fcb0f3_y.jpg) ### Hampton Inn Harriman Woodbury 10/10 Excellent "Great place. Clean room, good breakfast options, good facility. Highly recommend." [](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 6/10 Okay "The design of the room made it impossible to watch TV and control it from bed. Very odd. " [](https://expedia.com/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information) ![Holiday Inn Express & Suites Middletown - Goshen by IHG](https://images.trvl-media.com/lodging/42000000/41530000/41524600/41524586/78d303c2_y.jpg) ### Holiday Inn Express & Suites Middletown - Goshen by IHG 10/10 Excellent "Breakfast was ok, some of the items ran out. " [](https://expedia.com/Newburgh-Hotels-Holiday-Inn-Express-Suites-Middletown-Goshen.h41524586.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 10/10 Excellent "We had a great stay! Our room was clean, and the hotel was conveniently located just a 15-minute drive from LEGOLAND. The breakfast was also pretty good, which was a nice bonus. We would definitely stay here again!" [](https://expedia.com/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Middletown-Goshen](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/26de74c3_y.jpg) ### La Quinta Inn & Suites by Wyndham Middletown-Goshen 10/10 Excellent "Breakfast every morning was great , my kids loved the pool , staff helped us with everything we needed and the location was the best. " [](https://expedia.com/Middletown-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Middletown.h4098.Hotel-Information) ![Resorts World Catskills Casino](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/0479130a_y.jpg) ### Resorts World Catskills Casino 8/10 Good "Everything was Great except for staff in the hotel I didn’t find them to be Friendly at all. The Staff at the restaurant Bistro were exceptional and very Friendly." [](https://expedia.com/Monticello-Hotels-Resorts-World-Catskills-Casino.h23970267.Hotel-Information) ## Find out more about Middletown ## Middletown Villas information | Number of reviews | 19 | | ----------------- | --------- | | Accommodation | 26 Villas | | Lowest Price | $1,349 | | Highest Price | $1,349 | ## Frequently asked questions ### Why book your villa in Middletown with Expedia? ### How can I find cheap villas in Middletown? ### What is there to do near my villa in Middletown? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [New York Hotels ](https://www.expedia.com/New-York-Hotels.d178293.Travel-Guide-Hotels) - [Hotels near Paramount Theatre ](https://www.expedia.com/Paramount-Theatre-Hotels.0-l553248621561106035-0.Travel-Guide-Filter-Hotels) - [Hotels near Orange County Fair Speedway ](https://www.expedia.com/Orange-County-Fair-Speedway-Hotels.0-l6182288-0.Travel-Guide-Filter-Hotels) - [Hotels near Orange County Fairgrounds ](https://www.expedia.com/Orange-County-Fairgrounds-Hotels.0-l6225664-0.Travel-Guide-Filter-Hotels) - 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[Orange County Fair Speedway ](https://www.expedia.com/Orange-County-Fair-Speedway-Middletown.d6182288.Vacation-Attraction) - [Orange County Fairgrounds ](https://www.expedia.com/Orange-County-Fairgrounds-Middletown.d6225664.Vacation-Attraction) - [Visit New Hampton ](https://www.expedia.com/New-Hampton.dx177852) - [Galleria at Crystal Run ](https://www.expedia.com/Galleria-At-Crystal-Run-Middletown.d6225666.Vacation-Attraction) - [Soons Orchards ](https://www.expedia.com/Soons-Orchards-New-Hampton.d6229734.Vacation-Attraction) - [Visit Slate Hill ](https://www.expedia.com/Slate-Hill.dx6325187) - [Slate Hill Vacations ](https://www.expedia.com/Slate-Hill.d6325187.Destination-Travel-Guides) - [Visit Goshen ](https://www.expedia.com/Goshen.dx8005) - [Goshen Vacations ](https://www.expedia.com/Goshen.d8005.Destination-Travel-Guides) - [Orange County Genealogical Society ](https://www.expedia.com/Orange-County-Genealogical-Society-Goshen.d6209275.Vacation-Attraction) - [Goshen Historic Track ](https://www.expedia.com/Goshen-Historic-Track-Goshen.d553248621558786490.Vacation-Attraction) - 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