Title: Explore Middletown Vacation Packages, Book Now! | 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) ![](https://images.trvl-media.com/place/8005/8b2c54c4-af30-4521-9b56-3bdf0a8d1a15.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Middletown Vacations from $210 ## Book a Hotel + Flight or Car together to unlock savings Photo by Vincent Ramundo - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Your Middletown Vacation Our Middletown vacation packages allow you to create your own adventure. Tailor your journey to your needs and interests and make the most of your time in this fabulous city. [Orange County Fair Speedway](https://www.expedia.com/Orange-County-Fair-Speedway-Middletown.d6182288.Vacation-Attraction), [Galleria at Crystal Run](https://www.expedia.com/Galleria-At-Crystal-Run-Middletown.d6225666.Vacation-Attraction) and [Orange County Fairgrounds](https://www.expedia.com/Orange-County-Fairgrounds-Middletown.d6225664.Vacation-Attraction) are just a few of the many sights you'll want to see during your trip to Middletown. Your ultimate Middletown vacation is just clicks away. Browse hotels, airfares and more on Expedia for a getaway that's tailored to suit your travel style. ## The Latest Middletown vacation packages Price found within the past 48 hours. Click for updated prices. ![Sleep Inn & Suites Monroe - Woodbury](https://images.trvl-media.com/lodging/21000000/20600000/20597600/20597588/0db56af9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sleep Inn & Suites Monroe - Woodbury $210 per person Mar 20 - Mar 22 found 1 day ago Roundtrip flight included Atlanta (ATL) to Newburgh (SWF) 9.4/10 Exceptional! (1,004 reviews) We had a very nice stay. The room was so clean. The staff was Reviewed on Feb 2, 2026 ![Wildflower Farms, Auberge Collection](https://images.trvl-media.com/lodging/80000000/79880000/79873100/79873064/d940ee3d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Wildflower Farms, Auberge Collection Save 100% on your flight $3,670 per person Apr 23 - Apr 27 found 13 hours ago Roundtrip flight included Miami (MIA) to Newburgh (SWF) 9.4/10 Exceptional! (54 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 Reviewed on Dec 13, 2025 ![Hampton Inn & Suites Newburgh Stewart Airport](https://images.trvl-media.com/lodging/18000000/17270000/17262200/17262186/3df08b3c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hampton Inn & Suites Newburgh Stewart Airport $961 per person May 2 - May 6 found 1 day ago Roundtrip flight included Dallas (DFW) to Newburgh (SWF) 9.2/10 Wonderful! (967 reviews) Friendly staff. Spacious, clean room, and great indoor pool. Reviewed on Feb 2, 2026 ![Homewood Suites Stewart Airport](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/771d3275_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Homewood Suites Stewart Airport $1,098 per person May 2 - May 6 found 1 day ago Roundtrip flight included Dallas (DFW) to Newburgh (SWF) 9.2/10 Wonderful! (1,000 reviews) the room was clean and the hotel staff was nice. Reviewed on Jan 29, 2026 ![Caldwell House Bed & Breakfast](https://images.trvl-media.com/lodging/6000000/5120000/5112000/5111988/fdae1673_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Caldwell House Bed & Breakfast $818 per person Mar 13 - Mar 17 found 16 hours ago Roundtrip flight included Atlanta (ATL) to Newburgh (SWF) 9/10 Wonderful! (474 reviews) Great place to stay. Wonderful breakfasts. Gracious and warm hospitality. Reviewed on May 28, 2024 Don't see what you're looking for? See all available trips from Columbus to Middletown [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-06/2026-03-13/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=POU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### Discover the most popular places to visit in Middletown ![Ferris wheel at the sunset](https://images.trvl-media.com/place/6225664/2b018d28-992d-4453-aa8d-c427c6e3c18c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Orange County Fairgrounds 4.5/5(4 reviews) Enjoy an outing to Orange County Fairgrounds during your stay in Mechanicstown. Discover the area's festivals and churches. [](https://expedia.com/Orange-County-Fairgrounds-Middletown.d6225664.Vacation-Attraction) #### Orange County Fair Speedway 4/5(5 reviews) Catch an event at Orange County Fair Speedway during your trip to Mechanicstown. Discover the area's festivals and churches. [](https://expedia.com/Orange-County-Fair-Speedway-Middletown.d6182288.Vacation-Attraction) #### Galleria at Crystal Run 4/5(20 reviews) During your visit to Middletown, you can search for that perfect souvenir at Galleria at Crystal Run. While in this family-friendly area, you can savor the top-notch restaurants. [](https://expedia.com/Galleria-At-Crystal-Run-Middletown.d6225666.Vacation-Attraction) ## Middletown Hotel Deals ![La Quinta Inn & Suites by Wyndham Middletown-Goshen](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/77a42b8a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Quinta Inn & Suites by Wyndham Middletown-Goshen 551 Route 211 E Middletown NY Fully refundableReserve now, pay when you stay $103 nightly $122 total Feb 16 - Feb 17 Total with taxes and fees 9.2/10 Wonderful! (968 reviews) Clean room Reviewed on Feb 3, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F16%2F2026&endDate=2%2F17%2F2026&selected=4098&PinnedHotelID=4098&HadPinnedHotel=true®ionId=8864) ![Sleep Inn & Suites Middletown - Goshen](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/1b0779e7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sleep Inn & Suites Middletown - Goshen 3491 Route 6 Middletown NY Fully refundable $93 nightly $110 total Mar 2 - Mar 3 Total with taxes and fees 8.6/10 Excellent! (1,000 reviews) Yes Reviewed on Jan 20, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F2%2F2026&endDate=3%2F3%2F2026&selected=16700177&PinnedHotelID=16700177&HadPinnedHotel=true®ionId=8864) ![Hampton Inn by Hilton Middletown](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/8c9a3fbd_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn by Hilton Middletown 20 Crystal Run Crossing Middletown NY Fully refundableReserve now, pay when you stay $81 nightly $95 total Feb 26 - Feb 27 Total with taxes and fees 8.4/10 Very Good! (1,004 reviews) Staff was friendly and efficient. Bed comfy, super quiet & safe. I stayed only to sleep for a few hours during a snowstorm to be close to the hospital down the road so I didn’t have to drive far in the snow. It was expensive but worth the safe commute to work. Their parking lot was plowed and ... Reviewed on Jan 27, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F26%2F2026&endDate=2%2F27%2F2026&selected=281932&PinnedHotelID=281932&HadPinnedHotel=true®ionId=8864) [See all 1,481 properties in Middletown](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F7%2F2026&endDate=2%2F8%2F2026®ionId=8864) 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. ## Find the Best Middletown Vacation Packages ### Things to do in and around Middletown Middletown, New York, is perfect for families and city-themed vacations, offering a variety of activities to enjoy. Visitors can explore resorts, a shopping mall center, and local shopping options. Highlights include vacation tours, day tours, and golf getaways, making it easy to discover the charm of Middletown. Whether you're looking for great vacations or simply to explore the area, Middletown has something for everyone. **Shopping** For shopping, visit [Soons Orchards](https://www.expedia.com/Soons-Orchards-New-Hampton.d6229734.Vacation-Attraction), a public market just 3 miles away, offering local goods and a vibrant atmosphere. Mamakating Farmers Market, located 9 miles away, also provides a great selection. If you're up for a drive, check out the [Galleria at Crystal Run](https://www.expedia.com/Galleria-At-Crystal-Run-Middletown.d6225666.Vacation-Attraction) for a larger shopping experience. **Recreation** Enjoy a captivating performance at the [Paramount Theatre](https://www.expedia.com/Paramount-Theatre-Middletown.d553248621561106035.Vacation-Attraction), where culture and romance blend in a family-friendly atmosphere. For outdoor sports enthusiasts, [The Rock Sports Complex](https://www.expedia.com/The-Rock-Sports-Complex-Chester.d553248624556330411.Vacation-Attraction) offers exciting activities, while the [Scenic Farms Golf Course](https://www.expedia.com/Scenic-Farms-Golf-Course-Pine-Island.d553248621561164846.Vacation-Attraction) provides a serene environment to unwind and play a round of golf amidst beautiful landscapes. **Adventure** Experience thrilling races at [Orange County Fair Speedway](https://www.expedia.com/Orange-County-Fair-Speedway-Middletown.d6182288.Vacation-Attraction), where adrenaline meets excitement in the heart of Middletown. For family fun, visit [Castle Fun Center](https://www.expedia.com/Castle-Fun-Center-Chester.d6209270.Vacation-Attraction), a vibrant arcade and adventure zone located 9 miles away. If you love winter sports, head to [Mount Peter Ski Area](https://www.expedia.com/Mount-Peter-Ski-Area-Warwick.d553248621532664438.Vacation-Attraction), 15 miles from Middletown, for skiing adventures. **Nightlife** Middletown offers a vibrant nightlife with venues like the Paramount Theatre for live shows and The Last Lick for tasty drinks. Explore local bars on South Street for a laid-back vibe, and check out dance spots at nearby clubs for a lively evening. Enjoy the friendly atmosphere. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Find the best attractions in and around Middletown Middletown, New York, is an ideal destination for family vacations, offering a mix of city and entertainment-themed experiences. Visitors can explore urban parks, national state parks, and nearby lakes, perfect for outdoor adventures and family fun. Additionally, there's a local beach to enjoy, making Middletown a well-rounded spot for travelers seeking both relaxation and recreation in a vibrant setting. - **[Orange County Fairgrounds: ](https://www.expedia.com/Orange-County-Fairgrounds-Middletown.d6225664.Vacation-Attraction)** Experience the lively atmosphere at the Orange County Fairgrounds, a hub for outdoor family fun. Enjoy various events, from fairs to concerts, showcasing local culture and community spirit in a vibrant setting. - **[Harness Racing Museum and Hall of Fame: ](https://www.expedia.com/Harness-Racing-Museum-And-Hall-Of-Fame-Goshen.d6225670.Vacation-Attraction)** Dive into the rich history of harness racing at this unique museum. Located 6 miles from Middletown, it highlights the sport's culture and significance through engaging exhibits and memorabilia, perfect for sports enthusiasts. - **[Neversink River: ](https://www.expedia.com/Neversink-River-New-York.d681787877076414464.Vacation-Attraction)** Enjoy the breathtaking scenery along the Neversink River, situated 13 miles from Middletown. Ideal for nature lovers, this tranquil river offers opportunities for fishing, hiking, and picnicking amidst stunning outdoor vistas. ### Best time to go to Middletown The best time to visit Middletown can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Middletown falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Middletown falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 26.8°F (-2.9°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | February | 28.6°F (-1.9°C) | Light Rain | Mostly Cloudy | Average | Average | | March | 36.1°F (2.3°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | April | 47.5°F (8.6°C) | Light Rain | Mostly Sunny | Slightly High | Average | | May | 58.5°F (14.7°C) | Light Rain | Mostly Sunny | Average | Average | | June | 66.6°F (19.2°C) | Light Rain | Mostly Sunny | Slightly High | Average | | July | 72.7°F (22.6°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | August | 70.5°F (21.4°C) | Light Rain | Mostly Sunny | Average | Slightly High | | September | 63.7°F (17.6°C) | Light Rain | Mostly Sunny | Average | Average | | October | 52.7°F (11.5°C) | Light Rain | Mostly Sunny | Average | Slightly High | | November | 40.6°F (4.8°C) | Light Rain | Mostly Sunny | Slightly Low | Average | | December | 32.7°F (0.4°C) | Light Rain | Mostly Cloudy | Slightly Low | Slightly Low | ### Tips to save on your trip to Middletown - Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings. - Consider traveling during the off-peak season (typically March and December to January) for more affordable package holidays to Middletown. - Use the *Price per traveler* filter on Expedia to find a package deal that suits your budget. - Check the *VIP Access properties* filter to discover outstanding hotels with added member perks at select properties. ## Middletown Essential Information | Language | English | | --------------- | -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | Stewart Intl. Airport (SWF) | | Population | 27,800 | | Max Temp Winter | 35ºF | | Max Temp Summer | 80ºF | | Top Sights | [Warwick Valley Winery and Distillery](https://www.expedia.com/Warwick-Valley-Winery-And-Distillery-Warwick.d6087223.Vacation-Attraction), [Castle Fun Center](https://www.expedia.com/Castle-Fun-Center-Chester.d6209270.Vacation-Attraction) and [Paramount Theatre](https://www.expedia.com/Paramount-Theatre-Middletown.d553248621561106035.Vacation-Attraction) | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations 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[](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Middletown vacation package cost? ### What are the cheapest months to go to Middletown? ### How many days is enough for Middletown? ### Is it worth booking a vacation package to Middletown? ### How to find the best Middletown package deals? ### Is it cheaper to book a Middletown vacation as a package? ### When to book a vacation package to Middletown? ### How to plan a trip to Middletown? > 1. Choose when to travel: Check your diary and get packing. Your favorite season and the activities on offer will also help you decide when to escape to Middletown. > 2. Budget wisely: In addition to the price of your hotel, you should factor in other expenses too. These include flights, food and transportation. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Middletown. > 3. Use our [trip planning tool](https://www.expedia.com/why/trip-planning) to explore Middletown: Research every part of your trip to Middletown with this handy planner. Invite family or friends to collaborate on a group trip, search for hotels or things to do and make bookings. > 4. Decide how long to go away for: Now that you know more about Middletown, you can figure out the ideal length of your vacation. Create a rough itinerary and give yourself enough time to get through everything on your must-do list. > 5. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to choose a Middletown vacation package that brings all your bookings together. > 6. Book activities and experiences in advance: Whether it's entrance to a big attraction or a day trip in nature, you won't have to worry about missing out on the best Middletown has to offer. Find all the fun [things to do in Middletown](https://www.expedia.com/Things-To-Do-In-Middletown.d8864.Travel-Guide-Activities) with our dedicated activity guide. ### Does Expedia offer Book Now, Pay Later Middletown vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - More ways to book - [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) - [Mechanicstown Hotels ](https://www.expedia.com/Mechanicstown-Hotels.d553248634999219206.Travel-Guide-Hotels) - [New Hampton Hotels ](https://www.expedia.com/New-Hampton-Hotels.d177852.Travel-Guide-Hotels) - 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