Chesterfield Vacations from $263

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The Latest Chesterfield vacation packages

Price found within the past 48 hours. Click for updated prices.
Trumbull and Porter Hotel

Trumbull and Porter Hotel

3.5 out of 5
Corktown
Price was $340, price is now $263 per person
$263
per person
Dec 4 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
8.4/10 Very Good! (1,444 reviews)
We plan to stay here again. Compliments to the chef and a big thank you to the women behind the bar who made us feel welcome with her coversation and cocktails.

Reviewed on Nov 1, 2026

Saint John's Resort

Saint John's Resort

4 out of 5
Price was $631, price is now $401 per person
$401
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Detroit (DTW)
9.6/10 Exceptional! (1,001 reviews)

The Townsend Hotel

The Townsend Hotel

4 out of 5
Save 100% on your flight
Price was $592, price is now $420 per person
$420
per person
Dec 4 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
9.2/10 Wonderful! (797 reviews)

Holiday Inn Express & Suites Rochester Hill - Detroit Area by IHG

Holiday Inn Express & Suites Rochester Hill - Detroit Area by IHG

2.5 out of 5
Rochester Hills
Price was $751, price is now $562 per person
$562
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
8.6/10 Excellent! (618 reviews)

The Westin Detroit Metropolitan Airport

The Westin Detroit Metropolitan Airport

4 out of 5
Price was $807, price is now $642 per person
$642
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Detroit (DTW)
9/10 Wonderful! (1,004 reviews)

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Chesterfield Hotel Deals

Hampton Inn & Suites Detroit/Chesterfield Township

Hampton Inn & Suites Detroit/Chesterfield Township

2.5 out of 5
45725 Marketplace Blvd New Baltimore MI
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $97 total per night from Dec 1 to Dec 2
$97 total
Dec 1 - Dec 2
Total with taxes and fees
Hampton Inn & Suites Detroit/Chesterfield Township
Tru by Hilton Chesterfield Township Detroit

Tru by Hilton Chesterfield Township Detroit

2.5 out of 5
45301 Marketplace Blvd New Baltimore MI
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $90 total per night from Dec 1 to Dec 2
$90 total
Dec 1 - Dec 2
Total with taxes and fees
Tru by Hilton Chesterfield Township Detroit
Holiday Inn Express & Suites Chesterfield by IHG

Holiday Inn Express & Suites Chesterfield by IHG

2.5 out of 5
45825 Marketplace Blvd New Baltimore MI
Fully refundable
$92 nightly
The price is $100 total per night from Dec 1 to Dec 2
$100 total
Dec 1 - Dec 2
Total with taxes and fees
8.2/10 Very Good! (644 reviews)
"Great hotel"

Reviewed on Nov 1, 2026

Holiday Inn Express & Suites Chesterfield by IHG
See all 909 properties in Chesterfield
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.

Find the Best Chesterfield Vacation Packages

Chesterfield Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Windsor Airport (YQG)
Max Temp Winter
30ºF
Max Temp Summer
75ºF

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Frequently asked questions

Is Chesterfield better suited for a beach vacation or a cultural trip?
Chesterfield is primarily an urban destination known for its family-friendly attractions and outdoor activities. While you can enjoy water activities at places like Lake Saint Clair, about 16 miles away, or relax at Metro Beach, about 4 miles from central Chesterfield, the area's main draws are its entertainment and shopping.

A Chesterfield vacation is well-suited for travelers seeking a mix of recreation and urban amenities, with attractions like the amusement park C.J. Barrymore's about 7 miles away. Your package can be tailored to explore these diverse offerings.
How can I save money on a Chesterfield vacation package?
When you bundle, you can save up to 30%*. To save money on a Chesterfield package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What are the top things to do in Chesterfield?
A Chesterfield vacation offers a variety of attractions, from outdoor recreation to entertainment and shopping:

Browse and book things to do in Chesterfield on Expedia.
Do you need to rent a car in Chesterfield, or is public transport enough?
For a Chesterfield vacation package, renting a car is highly recommended for maximum flexibility. While Chesterfield is an urban destination, its family-friendly attractions and outdoor recreation spots are somewhat spread out.

For example, popular destinations like C.J. Barrymore's are about 7 miles from central Chesterfield, Metro Beach is about 4 miles away, and Lake Saint Clair is about 16 miles. A rental car included in your Chesterfield vacation packages with flights will allow you to easily explore these areas at your own pace. Your package hotel can serve as a convenient base for driving to these sights.
Can I change or cancel my Chesterfield vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Chesterfield vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Chesterfield vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Chesterfield vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Chesterfield?
To find last-minute vacation packages to Chesterfield, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Chesterfield vacation packages?
Free cancellation on a Chesterfield vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Chesterfield vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Chesterfield getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Chesterfield vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.