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Find Romantic Hotels in Middletown, NY

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Check availability on Middletown Romantic Hotels

Tonight
Nov 29 - Nov 30
Tomorrow
Nov 30 - Dec 1
Next weekend
Dec 5 - Dec 7
In two weeks
Dec 12 - Dec 14

Top Middletown Romantic Hotels

Courtyard
Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown

3.0 star property
Middletown
9.0 out of 10, Wonderful, (741)
"the room was very clean, friendly staff "
United States
Nyowa
The price is ￥22,365
￥26,967 total
includes taxes & fees
Dec 8 - Dec 9
Home2 Suites by Hilton Middletown
View from property
Residence Inn by Marriott Middletown Goshen

Residence Inn by Marriott Middletown Goshen

3.0 star property
Middletown
9.4 out of 10, Exceptional, (315)
"Room and service were excellent."
United States
Cymantha
The price is ￥25,090
￥29,637 total
includes taxes & fees
Dec 15 - Dec 16
Residence Inn by Marriott Middletown Goshen
Indoor pool, sun loungers
Best Western Hunt's Landing Hotel Matamoras/Milford

Best Western Hunt's Landing Hotel Matamoras/Milford

3.0 star property
Matamoras
8.4 out of 10, Very Good, (1016)
"Friendly staff, nice and clean room and breakfast area."
United States
Jean
The price is ￥14,205
￥15,483 total
includes taxes & fees
Dec 7 - Dec 8
Best Western Hunt's Landing Hotel Matamoras/Milford
Waterslide
The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

4.0 star property
Monticello
8.2 out of 10, Very Good, (1833)
"Amazing stayed at the resort, second time here and still planning to come in the future!"
United States
Yeshua
The Kartrite Resort & Indoor Waterpark
Property grounds
Resorts World Catskills Casino

Resorts World Catskills Casino

4.5 star property
Monticello
8.6 out of 10, Excellent, (1108)
"It is a great place to stay"
United States
Caonabo
Resorts World Catskills Casino
Restaurant
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1023)
"Parking was very easy, beautiful area, very nice staff"
United States
Elizabeth
The price is ￥15,996
￥18,096 total
includes taxes & fees
Dec 3 - Dec 4
Overlook Lodge at Bear Mountain
Bar (on property)
The Thayer Hotel at West Point

The Thayer Hotel at West Point

3.5 star property
West Point
9.0 out of 10, Wonderful, (659)
"Location was great & staying at a historic hotel was delightful."
United States
Bobby
The price is ￥24,543
￥31,823 total
includes taxes & fees
Dec 14 - Dec 15
The Thayer Hotel at West Point
7 bars/lounges
The Alder at Resorts World Catskills

The Alder at Resorts World Catskills

2.0 star property
Monticello
8.2 out of 10, Very Good, (198)
"Great place to stay "
United States
Darshan
The Alder at Resorts World Catskills
Mexican cuisine
La Posada

La Posada

2.5 star property
Milford
8.8 out of 10, Excellent, (100)
"Love the decor and very friendly staff"
United States
Janel
The price is ￥16,360
￥18,144 total
includes taxes & fees
Dec 1 - Dec 2
La Posada
Exterior detail
Borland House Inn

Borland House Inn

3.0 star property
Montgomery
9.2 out of 10, Wonderful, (144)
"Had a great stay at the the Borland House Inn a historical setting in a cute town with wonderful staff and a delicious breakfast"
United States
Deborah
Borland House Inn
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.
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Top Middletown Hotel Reviews

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"We love coming here. Clean, peaceful, lovely environment. Perfect place for family with small kids. "
Azuki 1-night trip
Posted 5 days ago
Overlook Lodge at Bear Mountain
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

10/10 Excellent
"Very friendly front desk staff!"
Robert 2-night trip
Posted 6 days ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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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.