Title: Book the Best Middletown LUXURY Hotels - Upscale Hotels in Middletown, NY | 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) ![](https://mediaim.expedia.com/destination/2/b3592d5854c5ebf058517b7fb1df474d.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Vincent Ramundo # Find luxury hotels in Middletown, NY ![](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 Luxury Hotels Tonight [Oct 11 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2025-10-11&endDate=2025-10-12&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2025-10-12&endDate=2025-10-13&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2025-10-17&endDate=2025-10-19&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=8864&startDate=2025-10-24&endDate=2025-10-26&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Middletown Luxury Hotels ![Room, 1 King Bed, Accessible, Bathtub](https://images.trvl-media.com/lodging/1000000/460000/459800/459783/63cc5778.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/460000/459800/459783/e6ceb5a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/460000/459800/459783/0189e9b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/1000000/460000/459800/459783/41ae9ead.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Middletown Middletown 6.2/10 (1003) "I had a wonderful stay and hope to see you again soon." CA $111 CA $131 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Newburgh-Hotels-Super-8-By-Wyndham-Middletown.h459783.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/77a42b8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/fed7909a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/0a5108cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/d1fd54a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Middletown-Goshen Middletown 9.4/10 Exceptional (856) "Place was great have stayed here many times." CA $163 CA $193 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Middletown-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Middletown.h4098.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1700000/1696000/1695948/1e5617f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/2000000/1700000/1696000/1695948/0c0f8192.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/2000000/1700000/1696000/1695948/ce61abbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1700000/1696000/1695948/558da38e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Microtel Inn & Suites by Wyndham Middletown Middletown 7.0/10 Good (1001) "The room was definitely clean & smelled good, the towels were soft. The bed & pillows nice & firm, yep, the One-day sleep was restful. Thnx.." CA $138 CA $163 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Newburgh-Hotels-Microtel-Inn-Suites-By-Wyndham-Middletown.h1695948.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=2025-10-25&endDate=2025-10-26®ionId=8864&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Find out more about Middletown ### Middletownand its attractions for luxury travelers Middletown, New York, offers a unique blend of luxury and adventure for discerning travellers. Begin your journey at the breathtaking Hudson Valley, where you can indulge in a hot air balloon ride for stunning aerial views of the lush landscape. Afterward, explore the intriguing artwork at the Galleria at Crystal Run, a premier shopping destination featuring high-end boutiques and charming eateries perfect for a leisurely afternoon. For those who appreciate the outdoors, the nearby Minnewaska State Park Preserve allows for luxurious picnics amidst scenic waterfalls and pristine hiking trails. Art enthusiasts will enjoy the vibrant cultural scene, with the Paramount Theatre hosting an array of performances in an ornate setting. When it comes to accommodation, consider staying at the elegant Westin New York at Times Square, known for its impeccable service and opulent amenities. After a day filled with exploration, unwind at the hotel’s spa, where tailored treatments provide the perfect retreat. With its convenient location and exceptional offerings, Middletown promises an unforgettable luxury experience for families seeking both relaxation and adventure. ## Top Middletown Hotel Reviews ![Hampton Inn Harriman Woodbury](//images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/c7d384a9_y.jpg) ### Hampton Inn Harriman Woodbury 10/10 Excellent "Found this hotel last year, it is super convenient for getting to the NY ren faire and has a Popeye's just up the driveway plus a whole shopping complex but you would never know when you are at the hotel. It is tucked all the way in the back and is nice & quiet. " [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![Overlook Lodge at Bear Mountain](//images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6_y.jpg) ### Overlook Lodge at Bear Mountain 10/10 Excellent "Incredibly peaceful when walking in the forest. Swimming in the lake and stream was amazing " [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Middletown-Goshen](//images.trvl-media.com/lodging/1000000/10000/4100/4098/77a42b8a_y.jpg) ### La Quinta Inn & Suites by Wyndham Middletown-Goshen 10/10 Excellent "Very clean room. Efficient staff" [](https://expedia.ca/Middletown-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Middletown.h4098.Hotel-Information) ![Best Western Hunt's Landing Hotel Matamoras/Milford](//images.trvl-media.com/lodging/1000000/30000/27300/27210/5acfc319_y.jpg) ### Best Western Hunt's Landing Hotel Matamoras/Milford 10/10 Excellent "I absolutely enjoyed my stay. The staff were friendly and the room was clean. The jacuzzi in the room was a great amenity. " [](https://expedia.ca/Matamoras-Hotels-Best-Western-Hunts-Landing-Hotel-MatamorasMilford.h27210.Hotel-Information) ![Super 8 by Wyndham Middletown](//images.trvl-media.com/lodging/1000000/460000/459800/459783/63cc5778_y.jpg) ### Super 8 by Wyndham Middletown 10/10 Excellent "It was good" [](https://expedia.ca/Newburgh-Hotels-Super-8-By-Wyndham-Middletown.h459783.Hotel-Information) ![Microtel Inn & Suites by Wyndham Middletown](//images.trvl-media.com/lodging/2000000/1700000/1696000/1695948/1e5617f9_y.jpg) ### Microtel Inn & Suites by Wyndham Middletown 10/10 Excellent "Excellent location about 45 minutes from Bethel. It was very clean. Waffles but no fruit at the free breakfast. I will stay here again when attending another show. " [](https://expedia.ca/Newburgh-Hotels-Microtel-Inn-Suites-By-Wyndham-Middletown.h1695948.Hotel-Information) ## Frequently asked questions ### Are you searching for a great accommodation for your luxury trip to Middletown? > Expedia can help you arrange a flight to Stewart Intl. Airport (SWF) airport, and then you can select from various places to stay that will deliver the luxury you'd like to find. Amenities are important when you plan a trip, so we make it easy to get what you'd like to make your stay relaxing and comfortable. If you want an upscale hotel with fine dining, a spa, or several swimming pools, Expedia can help you find the best luxury hotel experience that Middletown has to offer. During your visit, you might want to enjoy the restaurants which Middletown is known for. ### When can I expect good weather in Middletown? > Planning for the weather is an important factor for making your trip to Middletown a success, especially when you're splurging. The hottest months are usually July and August with an average temp of 68°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Middletown are January, February, March, and April, with each month seeing an average of 6 inches of snowfall. ### What's there to see and do in Middletown? > Take in the sights and attractions that Middletown offers with a visit to Paramount Theatre, Orange County Fair Speedway, and Orange County Fairgrounds. 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