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Check availability on Middletown Luxury Hotels

Our top choices for Middletown luxury hotels

Cromwell Manor Inn

Cromwell Manor Inn
4.0 star property
Cornwall
9.6 out of 10, Exceptional, (99 reviews)
The price is ¥38,495
¥45,472 total
includes taxes & fees
May 27 - May 28
Cromwell Manor Inn

Villa Verde BB Greenwood Lake NY

Villa Verde BB Greenwood Lake NY
4.0 star property
Monroe
10.0 out of 10, Exceptional, (19 reviews)
The price is ¥36,765
¥41,590 total
includes taxes & fees
May 18 - May 19
Villa Verde BB Greenwood Lake NY

Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection
5.0 star property
Gardiner
9.4 out of 10, Exceptional, (66 reviews)
  • cleanliness
    Mountain luxury resort with a full-service spa, outdoor pool, and upscale dining in serene wilderness surroundings.
The price is ¥207,402
¥240,800 total
includes taxes & fees
Jun 8 - Jun 9
Wildflower Farms, Auberge Collection

Resorts World Catskills Casino

Resorts World Catskills Casino
4.5 star property
Monticello
8.8 out of 10, Excellent, (1,118 reviews)
  • cleanliness
    Discover mountain majesty at this luxury Catskills retreat, where spa indulgences and casino thrills combine for an upscale escape.
The price is ¥26,738
¥34,145 total
includes taxes & fees
May 17 - May 18
Resorts World Catskills Casino

The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark
4.0 star property
Monticello
8.2 out of 10, Very Good, (2,184 reviews)
The price is ¥27,268
¥43,104 total
includes taxes & fees
May 17 - May 18
The Kartrite Resort & Indoor Waterpark

YO1 Longevity & Health Resorts, Catskills

YO1 Longevity & Health Resorts, Catskills
4.0 star property
Monticello
8.0 out of 10, Very Good, (522 reviews)
The price is ¥47,510
¥53,686 total
includes taxes & fees
Jun 7 - Jun 8
YO1 Longevity & Health Resorts, Catskills

Inn at Lake Joseph

Inn at Lake Joseph
4.0 star property
Forestburgh
8.4 out of 10, Very Good, (11 reviews)
The price is ¥44,167
¥49,909 total
includes taxes & fees
May 18 - May 19
Inn at Lake Joseph

Hotel Fauchere

Hotel Fauchere
4.0 star property
Milford
9.2 out of 10, Wonderful, (254 reviews)
The price is ¥50,271
¥54,795 total
includes taxes & fees
May 25 - May 26
Hotel Fauchere

John H Wallace House

John H Wallace House
4.0 star property
Milford
10.0 out of 10, Exceptional, (18 reviews)
The price is ¥32,210
¥35,109 total
includes taxes & fees
May 18 - May 19
John H Wallace House

The Chatwal Lodge

The Chatwal Lodge
4.0 star property
White Lake
9.8 out of 10, Exceptional, (8 reviews)
  • cleanliness
    Mountain retreat with deep-tissue massages, premium dining, and elegant fireplaces awaits.
The price is ¥133,611
¥150,981 total
includes taxes & fees
Jun 4 - Jun 5
The Chatwal Lodge
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.

Top Middletown Hotel Reviews

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 Orange County Community College.