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.
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.
Orange County Fairgrounds is 0.3 mi (0.6 km) from central Mechanicstown, why not stop by during your stay. If you have fun at Orange County Fairgrounds, you'll love LEGOLAND® New York, which isn't far.
Though Touro College of Osteopathic Medicine might be what brings you to town, perhaps you'll have a chance to explore more of Middletown while you are here.
Explore the historic Orange County Farmers Museum, showcasing antique farm equipment and rural life exhibits. Catch a show at the Paramount Theatre, a beautifully restored 1930s movie palace in the heart of downtown.
Check out reviews of Middletown hotels guests love
Overlook Lodge at Bear Mountain
10/10 Excellent
"The hotel is unique and provides so many amenities! First we were greeted by very friendly and helpful staff at check in! Our room was clean and the lodge has a beautiful common area and view. The zoo, museums and park area is amazing! So many trails to take all within the park. Can’t wait to come back this fall!! "
"The desk person on check in was fabulous. She really made a friend with my 10 yr old. She was super helpful and friendly. My only complaint was the shower curtain rod wasn't properly anchored. Had no effect on shower though. The 10 yr old loved the pattern on the bedspread."
"We had a wonderful stay. Dining options and shopping were no more than 10 minutes in either direction. Diner across the way serves good food too. Pool was clean. Breakfast was hot. Beds were comfortable. Can’t ask for more. "
Can I book refundable accommodations in Middletown?
If you want the flexibility to change your plans to Middletown, most accommodations provide refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.
Where should I stay in Middletown if I want an affordable accommodation?
Where can I stay in Middletown if I want a vacation home instead of a traditional hotel?
If you're looking for a good alternative to a hotel, browse our selection of 12 vacation homes.
What will the weather in Middletown be like during my visit?
July and August are typically the warmest months in Middletown when the average temp is 68°F. January and February are the coldest months when the average temperature is 31°F. October and July are the months with the most rain.
Why should I book my Middletown accommodation with Hotels.com?
There are lots of reasons to book your Middletown trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.
Find out more about Middletown
Find out more about Middletown
Middletown is a family-friendly place known for its restaurants. Nature lovers can visit Highland Lake and Thomas Bull Memorial Park. Popular sights in the surrounding area include LEGOLAND® New York.
