Chesterfield Vacations from $328

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The Latest Chesterfield vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Houze Detroit Downtown

Hotel Houze Detroit Downtown

3 out of 5
Downtown Detroit
Price was $429, price is now $328 per person
$328
per person
May 15 - May 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
8/10 Very Good! (155 reviews)
The check in process was a little taxing, but for the most part it was a great stay.

Reviewed on Mar 21, 2026

Graduate by Hilton Ann Arbor

Graduate by Hilton Ann Arbor

4 out of 5
Kerrytown
Save 100% on your flight
Price was $607, price is now $440 per person
$440
per person
May 16 - May 19
found 1 day ago
Roundtrip flight included
New York (NYC) to Detroit (DTW)
9/10 Wonderful! (1,010 reviews)
Great location. Excellent pub and amenities.

Reviewed on Mar 17, 2026

Saint John's Resort

Saint John's Resort

4 out of 5
Save 100% on your flight
Price was $662, price is now $490 per person
$490
per person
May 15 - May 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
9.6/10 Exceptional! (1,010 reviews)
A beautiful elegant facility

Reviewed on Mar 19, 2026

MotorCity Casino Hotel

MotorCity Casino Hotel

4.5 out of 5
North Corktown
Price was $482, price is now $365 per person
$365
per person
May 15 - May 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
8.8/10 Excellent! (4,563 reviews)
Clean room. shuttle to little ceasers arena was nice. Very friendly staff

Reviewed on Mar 21, 2026

Larkspur Landing Ann Arbor

Larkspur Landing Ann Arbor

2.5 out of 5
Thurston
Price was $471, price is now $361 per person
$361
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
New York (NYC) to Detroit (DTW)
8/10 Very Good! (1,017 reviews)
Stayed here while visiting a family member at U of M Hospital. Only stayed to sleep and shower. Convenient and easy to get back and forth. Staff was very friendly and helpful. The price was very reasonable. I have to say that the room and bathroom were one of the cleanest I’ve had in a hotel in a long time. And that’s something that is very important to me when traveling. The hotel isn’t the newest and fancy but the cleanliness makes up for it. I always say I only need clean and comfortable and this place met my needs very well. Will definitely stay here next time we are in town.

Reviewed on Mar 20, 2026

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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
$89 nightly
The price is $99 total per night from Apr 1 to Apr 2
$99 total
Apr 1 - Apr 2
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
.

Reviewed on Mar 21, 2026

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
$84 nightly
The price is $93 total per night from Apr 5 to Apr 6
$93 total
Apr 5 - Apr 6
Total with taxes and fees
8.8/10 Excellent! (420 reviews)
Nice!

Reviewed on Mar 22, 2026

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
$101 nightly
The price is $110 total per night from Mar 29 to Mar 30
$110 total
Mar 29 - Mar 30
Total with taxes and fees
8/10 Very Good! (574 reviews)
Room spotless! Staff very friendly. :

Reviewed on Feb 28, 2026

Holiday Inn Express & Suites Chesterfield by IHG
See all 946 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

How much does a Chesterfield vacation package cost?
Offering great value package deals from $328 on Expedia, you'll be thrilled with how little a vacation to Chesterfield costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chesterfield?
January, September and October are the best times to search for cheap Chesterfield vacation packages. Opting to travel in less busy periods means you can usually find better prices on flights and hotels.
How many days is enough for Chesterfield?
With a well-planned itinerary, you can easily hit the top Chesterfield attractions in a few days. But if you'd like to discover hidden gems or go on day trips, think about booking your Chesterfield vacation for longer.
How to find the best Chesterfield package deals?
Use Expedia's handy filters to find some of the best Chesterfield package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Chesterfield package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Chesterfield vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll usually land a better deal than booking each component separately. And you'll still have the flexibility to create a customized Chesterfield vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Chesterfield?
If you have your Chesterfield travel dates confirmed, book as soon as you can to bag some fantastic deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are great for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Chesterfield vacation packages?
Secure your dream escape to Chesterfield with our Book Now, Pay Later vacations. There's no need to save like crazy or wait until payday — we've partnered with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans let you spread the cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's a breeze to stay on budget and snap up travel deals before they sell out.

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