Title: Middletown Vacation Packages & Trips 2026 from CA $563 | 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) ![](https://images.trvl-media.com/place/8005/8b2c54c4-af30-4521-9b56-3bdf0a8d1a15.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Middletown Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Vincent Ramundo - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 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.ca/Orange-County-Fair-Speedway-Middletown.d6182288.Vacation-Attraction), [Galleria at Crystal Run](https://www.expedia.ca/Galleria-At-Crystal-Run-Middletown.d6225666.Vacation-Attraction) and [Orange County Fairgrounds](https://www.expedia.ca/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. ## Top Middletown Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Sleep Inn & Suites Middletown - Goshen](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/aeade474_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sleep Inn & Suites Middletown - Goshen CA $563 per person Apr 24 - Apr 26 found 23 hours ago Roundtrip flight included Montreal (YUL) to Newburgh (SWF) 8.6/10 Excellent! (1,015 reviews) Clean room, safe and staff is courteous Reviewed on Mar 19, 2026 ![Courtyard by Marriott Newburgh Stewart Airport](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/7494afa4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Courtyard by Marriott Newburgh Stewart Airport CA $871 per person Jun 6 - Jun 10 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Newburgh (SWF) 8.2/10 Very Good! (712 reviews) Issues with heat in the room, windows did not close Reviewed on Mar 21, 2026 ![Candlewood Suites Middletown Goshen by IHG](https://images.trvl-media.com/lodging/110000000/109760000/109754400/109754354/e4a61882_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Candlewood Suites Middletown Goshen by IHG CA $909 per person Apr 29 - May 3 found 1 day ago Roundtrip flight included Toronto (YYZ) to Newburgh (SWF) 9.2/10 Wonderful! (43 reviews) Amazing property with accommodating staff. The best hotel in Middletown! Reviewed on Mar 20, 2026 ![Holiday Inn Express Hotel & Suites Chester by IHG](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/8648b91b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Express Hotel & Suites Chester by IHG CA $1,170 per person May 1 - May 5 found 20 hours ago Roundtrip flight included Montreal (YUL) to Newburgh (SWF) 8.6/10 Excellent! (1,008 reviews) We have been several times during the past few years the hotel is in very good condition and the coffee is really good available 24 hours a day the breakfast has several choices that are good the rooms are clean the A/C and heat work great overall great place to stay we come sometimes for a quick weekend getaway from New York City will continue to come back. Great local diner and restaurants. Reviewed on Mar 22, 2026 ![Holiday Inn Express & Suites Middletown - Goshen by IHG](https://images.trvl-media.com/lodging/42000000/41530000/41524600/41524586/78d303c2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Express & Suites Middletown - Goshen by IHG CA $985 per person May 1 - May 5 found 20 hours ago Roundtrip flight included Montreal (YUL) to Newburgh (SWF) 8.8/10 Excellent! (704 reviews) Very comfortable stay. Beautiful and spotless rooms. Nice fridge. Friendly staff ! Reviewed on Feb 16, 2026 ## Ready to book your vacation to Middletown? Choose your dates ## Middletown Hotel Deals ![Sleep Inn & Suites Middletown - Goshen](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/aeade474_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sleep Inn & Suites Middletown - Goshen 3491 Route 6 Middletown NY Fully refundable CA $139 CA $164 total Mar 31 - Apr 1 includes taxes & fees 8.6/10 Excellent! (1,003 reviews) Clean room, safe and staff is courteous Reviewed on Mar 19, 2026 [](https://expedia.ca/Hotel-Search?startDate=31%2F03%2F2026&endDate=01%2F04%2F2026&selected=16700177&PinnedHotelID=16700177&HadPinnedHotel=true®ionId=8864) ![Courtyard by Marriott Middletown Goshen](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/5a64b5a6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Courtyard by Marriott Middletown Goshen 24 Crystal Run Xing Middletown NY Fully refundableReserve now, pay when you stay CA $127 CA $150 total Apr 1 - Apr 2 includes taxes & fees 8.6/10 Excellent! (1,008 reviews) Was very clean and nice Reviewed on Mar 22, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F04%2F2026&endDate=02%2F04%2F2026&selected=921424&PinnedHotelID=921424&HadPinnedHotel=true®ionId=8864) ![La Quinta Inn & Suites by Wyndham Middletown-Goshen](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/26de74c3_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 CA $166 CA $196 total Mar 26 - Mar 27 includes taxes & fees 9.4/10 Exceptional! (986 reviews) Laundry room clean too Clean staff very nice Reviewed on Mar 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F03%2F2026&endDate=27%2F03%2F2026&selected=4098&PinnedHotelID=4098&HadPinnedHotel=true®ionId=8864) [See all 1,491 properties in Middletown](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F03%2F2026&endDate=26%2F03%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. ![](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.ca/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 [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Discover the most popular places to visit in Middletown #### Orange County Fair Speedway Catch an event at Orange County Fair Speedway during your trip to Mechanicstown. Discover the area's festivals and churches. [](https://expedia.ca/Orange-County-Fair-Speedway-Middletown.d6182288.Vacation-Attraction) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app