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Find Casinos in Middletown, NY

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Check availability on Middletown Casinos

Our top choices for Middletown hotels with a casino

Courtyard
Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
3.0 star property
Middletown
9.0 out of 10, Wonderful, (744)
"Overall, it was a good one-night stay. The room was clean and spacious, and parking was convenient. However, the breakfast needs significant improvement; the coffee, eggs, and bacon were all served cold. Additionally, the dining area lacked short tables for children to comfortably sit and eat."
United States
JENNY
The price is NT$4,465
NT$5,384 total
includes taxes & fees
Jan 10 - 2026/1/11
Home2 Suites by Hilton Middletown
Free daily on-the-go breakfast
Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG
2.5 star property
Montgomery
8.8 out of 10, Excellent, (795)
"Good stay"
United States
Fatima
The price is NT$2,806
NT$3,175 total
includes taxes & fees
Jan 4 - 2026/1/5
Holiday Inn Express & Suites Montgomery by IHG
Casino
Resorts World Catskills Casino

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
Room, 2 Queen Beds, Non Smoking | In-room safe, desk, iron/ironing board, free cribs/infant beds
Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro
2.0 star property
Wurtsboro
7.6 out of 10, Good, (593)
"I love "
United States
Niralkumar
The price is NT$3,088
NT$3,490 total
includes taxes & fees
Jan 2 - 2026/1/3
Days Inn by Wyndham Wurtsboro
Casino
The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark
4.0 star property
Monticello
8.2 out of 10, Very Good, (1855)
"Friendly staff , clean , beautiful design in the hotel and decor . "
United States
Lusvianca
The price is NT$4,749
NT$7,354 total
includes taxes & fees
Jan 8 - 2026/1/9
The Kartrite Resort & Indoor Waterpark
Exterior
Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point
2.0 star property
Newburgh
6.0 out of 10, (1001)
"nice bed"
United States
david
The price is NT$2,429
NT$2,869 total
includes taxes & fees
Dec 21 - Dec 22
Howard Johnson by Wyndham Newburgh/West Point
Exterior detail
Borland House Inn

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
Lobby sitting area
YO1 Longevity & Health Resorts, Catskills

YO1 Longevity & Health Resorts, Catskills

YO1 Longevity & Health Resorts, Catskills
4.0 star property
Monticello
8.0 out of 10, Very Good, (503)
"Get stay. Loved the amenities "
United States
Bernie
The price is NT$10,267
NT$11,601 total
includes taxes & fees
Dec 22 - Dec 23
YO1 Longevity & Health Resorts, Catskills
Dinner and brunch served, alfresco dining
The Bradstan Boutique Hotel

The Bradstan Boutique Hotel

The Bradstan Boutique Hotel
3.5 star property
Eldred
9.8 out of 10, Exceptional, (116)
"This place is so lovely. My family had a wonderful Thanksgiving holiday here. "
United States
Sandi
The price is NT$12,208
NT$14,262 total
includes taxes & fees
Jan 2 - 2026/1/3
The Bradstan Boutique Hotel
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

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Frequently asked questions

Searching for casino hotels in Middletown?
Headed to Middletown for some gaming? As luck would have it, you'll find Resorts World Catskills, situated 18.6 mi (30 km) away, and Resorts World Hudson Valley, 18.9 mi (30.4 km) away, plus much more to see and do. Visitors enjoy the family-friendly activities, shopping, and dining options.
How many hotels that are good for gaming should I expect to find in Middletown?
Win big at one of Expedia's 43 lodging options close to the casinos in Middletown.
When should I take my casino trip to Middletown?
You might spend a lot of your vacation inside, but if you want to see more of the area, taking a look at local weather data can help you. 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?
You can head to Galleria at Crystal Run, Soons Orchards, or Mamakating Farmers Market to shop for the perfect souvenir. Places like Harness Racing Museum and Hall of Fame, Neversink Valley Area Museum, and Neversink Valley Museum of History & Innovation offer a glimpse of local culture. If you're looking to add to your itinerary, you can also visit Paramount Theatre and Orange County Fair Speedway.
What are my transportation options for my casino getaway to Middletown?
Here are some transportation options in Middletown: You can arrange a flight to the nearest airport, which is Stewart Intl. Airport (SWF), 17.8 mi (28.7 km) from the city center. If you'd like to explore around the area, you may want to rent a car for your trip.