Chesterfield Vacations from $340

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The Latest Chesterfield vacation packages

Price found within the past 48 hours. Click for updated prices.
American Inn and Suites Dundee

American Inn and Suites Dundee

2 out of 5
Price was $492, price is now $340 per person
$340
per person
Mar 13 - Mar 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Detroit (DTW)
6.8/10 (962 reviews)
The bed was made, front desk was nice. Cleaning people banged on our door promptly at 11.

Reviewed on Oct 27, 2025

Saint John's Resort

Saint John's Resort

4 out of 5
Save 100% on your flight
Price was $558, price is now $349 per person
$349
per person
Mar 3 - Mar 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
9.6/10 Exceptional! (1,004 reviews)
Absolutely beautiful facility and grounds. Mini restaurants, large updated rooms, and excellent service. I will definitely be back.

Reviewed on Jan 6, 2026

Graduate by Hilton Ann Arbor

Graduate by Hilton Ann Arbor

4 out of 5
Kerrytown
Save 100% on your flight
Price was $621, price is now $428 per person
$428
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
9.2/10 Wonderful! (1,003 reviews)
Clean room and great staff

Reviewed on Jan 9, 2026

Weber's Hotel & Restaurant

Weber's Hotel & Restaurant

4 out of 5
Lakewood
Price was $635, price is now $461 per person
$461
per person
Mar 13 - Mar 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Detroit (DTW)
9.4/10 Exceptional! (1,410 reviews)
Friendly staff, clean and close to University!

Reviewed on Jan 5, 2026

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Chesterfield Hotel Deals

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
$81 nightly
The price is $90 total per night from Jan 20 to Jan 21
$90 total
Jan 20 - Jan 21
Total with taxes and fees
8.6/10 Excellent! (373 reviews)
Clean room, friendly staff, good location

Reviewed on Jan 1, 2026

Tru by Hilton Chesterfield Township Detroit
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 Jan 19 to Jan 20
$99 total
Jan 19 - Jan 20
Total with taxes and fees
8.4/10 Very Good! (1,000 reviews)
Yes

Reviewed on Jan 8, 2026

Hampton Inn & Suites Detroit/Chesterfield Township
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 Jan 13 to Jan 14
$110 total
Jan 13 - Jan 14
Total with taxes and fees
8/10 Very Good! (559 reviews)
Amazing all the way around!

Reviewed on Jan 5, 2026

Holiday Inn Express & Suites Chesterfield by IHG
See all 941 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 $340 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.