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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

Premium bedding, down comforters, minibar, in-room safe
Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection
5.0 star property
Gardiner
9.4 out of 10, Exceptional, (58)
"Everything was ok, except for the fact that we couldn’t do late check out or that we payed a bit more for a standard room. But everything else was perfect "
United States
Sandra N
The price is ￥193,304
￥223,199 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Wildflower Farms, Auberge Collection
Frette Italian sheets, premium bedding, pillowtop beds, free minibar
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 ￥139,509
￥157,645 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Chatwal Lodge
Property grounds
Resorts World Catskills Casino

Resorts World Catskills Casino

Resorts World Catskills Casino
4.5 star property
Monticello
8.6 out of 10, Excellent, (1110)
"It is a great place to stay"
United States
Caonabo
Resorts World Catskills Casino
Exterior
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 ￥40,222
￥47,513 total
includes taxes & fees
Dec 24 - Dec 25
Cromwell Manor 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 ￥51,037
￥57,671 total
includes taxes & fees
Dec 18 - Dec 19
YO1 Longevity & Health Resorts, Catskills
Waterslide
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, (1862)
"Friendly staff , clean , beautiful design in the hotel and decor . "
United States
Lusvianca
The price is ￥24,678
￥37,763 total
includes taxes & fees
Dec 18 - Dec 19
The Kartrite Resort & Indoor Waterpark
Free daily continental breakfast
Hotel Fauchere

Hotel Fauchere

Hotel Fauchere
4.0 star property
Milford
9.2 out of 10, Wonderful, (247)
Hotel Fauchere
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 ￥44,125
￥49,862 total
includes taxes & fees
Dec 28 - Dec 29
Inn at Lake Joseph
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 ￥25,677
￥32,148 total
includes taxes & fees
Dec 17 - Dec 18
Villa Verde BB Greenwood Lake NY
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 ￥26,200
￥28,558 total
includes taxes & fees
Dec 18 - Dec 19
John H Wallace House
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
"Wonderful hotel "
Ruthie 2-night trip
Posted 3 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.