Are there any 5-star holiday rentals in Darien?

Our site doesn't offer any 5-star holiday rentals in Darien. However, you can still find some top-rated retreats where the only thing on your itinerary will be to unpack and have fun. See what's available by checking out our holiday rentals in Darien .

5 Stars Hotels in Darien: Special Rates & Discounts

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Our top choices for Darien 5-star hotels

A high-rise hotel with a prominent 'TRUMP' sign, reflecting in the water, surrounded by other tall buildings.

1. Trump International Hotel & Tower Chicago

Downtown Chicago

Matthew

HK$4,303 total

includes taxes & fees

15 Nov - 16 Nov

A modern hotel lobby with a reception desk, seating area, and large windows offering city views.

2. The Langham, Chicago

Downtown Chicago

Courtney

HK$4,870 total

includes taxes & fees

6 Dec - 7 Dec

A modern indoor swimming pool with a clear blue water surface, a wooden ceiling, and a wall with a floral pattern.

3. Nobu Hotel Chicago

Downtown Chicago

Abhay

HK$3,439 total

includes taxes & fees

22 Nov - 23 Nov

A rooftop dining area with checkered tablecloths, red and blue plates, and a city skyline in the background.

4. Art Villa

West Town

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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Darien.

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

HK$1,594

HK$1,871 total

28 Nov - 29 Nov

includes taxes & fees

8.6/10 Excellent! (2,589 reviews)

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Pool Spa Hot tub Breakfast included Waterpark

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 Darien

Explore the scenic trails of Waterfall Glen Forest Preserve where locals jog through woodlands and past limestone bluffs. Families gather at Darien Community Park for summer concerts, splash pad fun, and well-maintained sports fields.

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Frequently asked questions

How much does it cost to stay in a 5-star hotel in Darien?

How much you pay for a 5-star hotel in Darien can vary depending on what time of year you travel and how long you plan to stay, among other factors. Take advantage of our price per night filter and other search tools to land the best rate on an indulgent stay.

Search for the lowest price per night from HK$1,073

What makes a hotel 5 stars in Darien?

In Darien, a hotel needs to provide a certain number of upscale amenities to earn 5 stars. These may include on-site gyms, gourmet restaurants, saunas and spas, premium bedding, luxury toiletries and more. What also sets 5-star hotels apart is their extraordinary service. You can look forward to things like in-room massages, concierge services and nightly turn-down services. Some may even offer additional touches like welcome gifts.

Are there any 5-star all-inclusive resorts in Darien?

Our handy filters are the best way to search for exactly what you want. Select "All inclusive" and "5-star" to see the most luxurious hotels in Darien where your accommodation, meals, activities and entertainment are included in the upfront price. At these retreats, your trip is pure indulgence from the moment you check in.

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Our top choices for Darien 5-star hotels