A lake surrounded by autumn-colored trees reflecting on the water.

Compare and book 5 Star hotels in Middletown, New York

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Middletown 5 Star Hotels

Tonight
14 Oct - 15 Oct
Tomorrow
15 Oct - 16 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Middletown 5-star hotels

A spacious outdoor seating area with a central fire pit, wooden flooring, and a view of a green landscape.
A modern indoor pool area with a seating arrangement overlooking a scenic view.
A spacious room with wooden beams, large windows, and a view of a lake surrounded by trees.
A wooden deck with a hot tub, a table with glasses and towels, and a couple in bathrobes.

1. Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection
Gardiner
United States
Alison
37.526.368 ₫
43.428.996 ₫ total
includes taxes & fees
4 Nov - 5 Nov
Wildflower Farms, Auberge Collection
Save an average of 15% on thousands of hotels when you're signed in

Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Middletown.
The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

555 Resorts World Drive Monticello NY
4.194.504 ₫
6.587.082 ₫ total
15 Oct - 16 Oct
includes taxes & fees
8.2/10 Very good! (2,464 reviews)
The Kartrite Resort & Indoor Waterpark
Resorts World Catskills Casino

Resorts World Catskills Casino

888 Resorts World Drive Monticello NY
4.612.985 ₫
5.860.572 ₫ total
21 Oct - 22 Oct
includes taxes & fees
8.8/10 Excellent! (1,279 reviews)
Resorts World Catskills Casino
New Paltz Way Hotel

New Paltz Way Hotel

11 Water St New Paltz NY
8.539.529 ₫
10.870.441 ₫ total
2 Nov - 3 Nov
includes taxes & fees
9.2/10 Wonderful! (30 reviews)
New Paltz Way Hotel
Still don't see what you're looking for?
See all properties in Middletown.
You can also use these popular filters to refine your search.
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.

Learn more about Middletown

Just an hour from NYC, this historic Hudson Valley town offers scenic hikes along the Heritage Trail and apple picking at local orchards. Explore the interactive exhibits at the National Soaring Museum, then catch a performance at the beautifully restored Paramount Theatre built in 1930.

See all hotels in Middletown
A lake surrounded by autumn-colored trees reflecting on the water.

Top Middletown Hotel Reviews

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Middletown?
How much you pay for a 5-star hotel in Middletown depends on things like when you plan to go and the length of your escape. Our insider tip for bagging an awesome deal? Use our pricing filters to check out the available accommodation for your chosen dates.
  • Search for the lowest price per night from 5.860.572 ₫
What makes a hotel 5 stars in Middletown?
In Middletown, a hotel needs to offer a certain amount of high-end amenities to be designated 5 stars. These may include on-site gyms, saunas and spas, gourmet restaurants, luxury toiletries, premium bedding and more. What also sets 5-star hotels apart is their superior service. You'll enjoy things like nightly turn-down services, in-room massages and concierge services. Some may even offer special touches such as welcome gifts.
Are there any 5-star all-inclusive resorts in Middletown?
Use Expedia's filters to find a luxurious escape in Middletown where everything you need is included. From there, narrow down your results for accommodation that have 5 stars and are deemed "All inclusive." The first thing on the schedule at these stays? Pure enjoyment and indulgence.

Explore a world of travel with Expedia