Chesterfield Vacations from $391

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The Latest Chesterfield vacation packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Ann Arbor North

DoubleTree by Hilton Ann Arbor North

4 out of 5
Thurston
Save 100% on your flight
Price was $552, price is now $391 per person
$391
per person
Jul 10 - Jul 13
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
8.4/10 Very Good! (1,004 reviews)
This was a very average hotel that was not in the best location that charged me to park in their giant parking lot. Seems like a money grab.

Reviewed on May 3, 2026

Staybridge Suites Ann Arbor- Univ of Michigan by IHG

Staybridge Suites Ann Arbor- Univ of Michigan by IHG

3 out of 5
Bryant Pattengill East
Save 100% on your flight
Price was $803, price is now $464 per person
$464
per person
Jul 4 - Jul 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
8.8/10 Excellent! (635 reviews)
Right across the street

Reviewed on May 17, 2026

Saint John's Resort

Saint John's Resort

4 out of 5
Save 100% on your flight
Price was $1,868, price is now $1,097 per person
$1,097
per person
Jul 4 - Jul 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
9.6/10 Exceptional! (1,002 reviews)
Proposed to my Wife here in the garden...unforgettable experience!!!

Reviewed on May 27, 2026

The Townsend Hotel

The Townsend Hotel

4 out of 5
Save 100% on your flight
Price was $1,116, price is now $723 per person
$723
per person
Jul 5 - Jul 9
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Detroit (DTW)
9.2/10 Wonderful! (749 reviews)
The property has a great location and very well maintained. The staff was very helpful at all times.

Reviewed on Apr 21, 2026

Weber's Hotel & Restaurant

Weber's Hotel & Restaurant

4 out of 5
Lakewood
Save 100% on your flight
Price was $636, price is now $454 per person
$454
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
9.4/10 Exceptional! (1,561 reviews)
I think it would need carpet replacement especially in the rooms.The bathrooms are beautiful and clean. Very nice bed and bedsheets . Very good breakfast buffet on Sunday and excellent seafood on the menu.

Reviewed on May 19, 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
$83 nightly
The price is $92 total per night from Jun 23 to Jun 24
$92 total
Jun 23 - Jun 24
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
"The room was clean and the beds were soft. The pool was clean and not crowded. Would go there again."

Reviewed on May 25, 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
$100 nightly
The price is $111 total per night from May 31 to Jun 1
$111 total
May 31 - Jun 1
Total with taxes and fees
8.8/10 Excellent! (441 reviews)
"Great hotel with clean rooms, friendly staff, and a convenient location. The breakfast was good, and the overall experience was comfortable and enjoyable. Would stay again!"

Reviewed on May 26, 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
$122 nightly
The price is $133 total per night from May 31 to Jun 1
$133 total
May 31 - Jun 1
Total with taxes and fees
8/10 Very Good! (592 reviews)
"Great stay"

Reviewed on May 18, 2026

Holiday Inn Express & Suites Chesterfield by IHG
See all 944 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 $391 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.