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Find Luxury Hotels in Middletown, NY

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Check availability on Middletown Luxury Hotels

Our top choices for Middletown luxury hotels

Resort view
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
Water park
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, (1858)
"Friendly staff , clean , beautiful design in the hotel and decor . "
United States
Lusvianca
The price is ￥24,805
￥37,959 total
includes taxes & fees
Dec 14 - Dec 15
The Kartrite Resort & Indoor Waterpark
Exterior
Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection
5.0 star property
Gardiner
9.4 out of 10, Exceptional, (56)
"Great stay"
United States
Adrienne
The price is ￥192,277
￥222,081 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Wildflower Farms, Auberge Collection
Outdoor wedding area
John H Wallace House

John H Wallace House

John H Wallace House
4.0 star property
Milford
10.0 out of 10, Exceptional, (14)
"The John H. Wallace House is a welcoming and comfortable place to stay. Don’t hesitate to make a reservation to go there. "
United States
Barbara
The price is ￥26,851
￥29,268 total
includes taxes & fees
Dec 22 - Dec 23
John H Wallace House
Meeting facility
Hotel Fauchere

Hotel Fauchere

Hotel Fauchere
4.0 star property
Milford
9.2 out of 10, Wonderful, (247)
"Great place to visit. Amazing food options, beautiful town overall!"
United States
Oleg
Hotel Fauchere
Exterior
The Chatwal Lodge

The Chatwal Lodge

The Chatwal Lodge
4.0 star property
White Lake
9.8 out of 10, Exceptional, (7)
"Excellent experience serene calming and rejuvenating "
United States
tapti
The price is ￥111,953
￥126,507 total
includes taxes & fees
Dec 21 - Dec 22
The Chatwal Lodge
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 ￥51,195
￥57,850 total
includes taxes & fees
Dec 21 - Dec 22
YO1 Longevity & Health Resorts, Catskills
Terrace/patio
Cromwell Manor Inn

Cromwell Manor Inn

Cromwell Manor Inn
4.0 star property
Cornwall
9.4 out of 10, Exceptional, (94)
"Great stay!"
United States
Amrita
The price is ￥40,390
￥47,710 total
includes taxes & fees
Dec 18 - Dec 19
Cromwell Manor Inn
Exterior
Villa Verde BB Greenwood Lake NY

Villa Verde BB Greenwood Lake NY

Villa Verde BB Greenwood Lake NY
4.0 star property
Monroe
10.0 out of 10, Exceptional, (13)
"Amazing breakfast, scenery, tucked away on a hilltop, what a getaway! "
United States
Gary
The price is ￥27,839
￥34,609 total
includes taxes & fees
Dec 14 - Dec 15
Villa Verde BB Greenwood Lake NY
Front of property
Inn at Lake Joseph

Inn at Lake Joseph

Inn at Lake Joseph
4.0 star property
Forestburgh
8.4 out of 10, Very Good, (9)
"amazing staff and wonderful place to stay"
United States
Daniel
The price is ￥45,411
￥51,316 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Inn at Lake Joseph
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

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

10/10 Excellent
"He was excellent our two nights and thank again, see you soon."
Abdou karime 2-night trip
Posted 6 days ago
Hampton Inn Harriman Woodbury

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Frequently asked questions

Are you searching for a great accommodation for your luxury trip to Middletown?
Expedia can help you arrange a flight to Stewart Intl. Airport (SWF) airport, and then you can select from various places to stay that will deliver the luxury you'd like to find. Amenities are important when you plan a trip, so we make it easy to get what you'd like to make your stay relaxing and comfortable. If you want an upscale hotel with fine dining, a spa, or several swimming pools, Expedia can help you find the best luxury hotel experience that Middletown has to offer. During your visit, you might want to enjoy the restaurants which Middletown is known for.
When can I expect good weather in Middletown?
Planning for the weather is an important factor for making your trip to Middletown a success, especially when you're splurging. 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's there to see and do in Middletown?
Take in the sights and attractions that Middletown offers with a visit to Paramount Theatre, Orange County Fair Speedway, and Orange County Fairgrounds. If you have some spare time during your trip, you might want to check out Galleria at Crystal Run and Highland Lake.