A large steel bridge spanning a river, surrounded by trees and buildings.

Find Romantic Hotels in Middletown, NY

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Check availability on Middletown Romantic Hotels

This weekend
Jun 26 - Jun 28
Next weekend
Jul 3 - Jul 5

Top Middletown Hotel Reviews

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

8/10 Good
"Very decent property for the price level. Loud neighborhood, though Room was great!!!"
Miguel Eduardo 4-night trip
Posted 10 hours ago
Overlook Lodge at Bear Mountain
Best Western Hunt's Landing Hotel Matamoras/Milford

Best Western Hunt's Landing Hotel Matamoras/Milford

10/10 Excellent
"One of the best b-fast foods, esp the yogurt machine. comfortable king bed, knowledgeable staff for local supermarket. Very clean, large b-fast dining area. Great value for the price."
Ivan 1-night trip
Posted 1 day ago
Best Western Hunt's Landing Hotel Matamoras/Milford

Frequently asked questions

Searching for romantic hotels in Middletown?
Are you and your partner looking for a romantic getaway? Our guests also enjoy Middletown for its restaurants and shopping. If you want to explore the area, you might head to Paramount Theatre, Orange County Fair Speedway, or Orange County Fairgrounds. If you're interested in staying near a certain attraction, you can sort properties by neighborhood or distance to top landmarks, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Middletown?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Middletown: 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 is there to do in Middletown?
There's nothing better than wandering around a new destination with your sweetheart, so consider checking out all there is to see and do in Middletown. If you and your partner are interested in sampling the area's cuisine, you'll love Middletown for its array of dining options. You might consider a visit to Paramount Theatre, Orange County Fair Speedway, or Orange County Fairgrounds.
What's the best way to get to Middletown and around town during my romantic getaway?
This information about transportation options in Middletown might help your romantic trip go off without a hitch: The closest major airport is Stewart Intl. Airport (SWF), located 17.8 mi (28.7 km) from the city center. If you'd like to venture out around the area, consider renting a car to take in more sights.

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