Chesterfield Vacations from $164

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The Latest Chesterfield vacation packages

Price found within the past 48 hours. Click for updated prices.
Larkspur Landing Ann Arbor

Larkspur Landing Ann Arbor

2.5 out of 5
Thurston
Price was $235, price is now $164 per person
$164
per person
May 29 - May 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
8/10 Very Good! (1,004 reviews)
Clean and good location to AA but the breakfast was completely picked over and not replenished. Ran out of pancakes, cream cheese, milk and sausage by 9am

Reviewed on Apr 12, 2026

Hotel Houze Detroit Downtown

Hotel Houze Detroit Downtown

3 out of 5
Downtown Detroit
Price was $371, price is now $228 per person
$228
per person
May 16 - May 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
8/10 Very Good! (200 reviews)
Very central location. Very suspicious rooms. I will return

Reviewed on Apr 12, 2026

Weber's Hotel & Restaurant

Weber's Hotel & Restaurant

4 out of 5
Lakewood
Save 100% on your flight
Price was $398, price is now $264 per person
$264
per person
May 29 - May 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
9.4/10 Exceptional! (1,519 reviews)
Lovely in every way. Staff amenities etc.

Reviewed on Apr 12, 2026

Saint John's Resort

Saint John's Resort

4 out of 5
Save 100% on your flight
Price was $665, price is now $450 per person
$450
per person
Jun 19 - Jun 21
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
9.6/10 Exceptional! (1,000 reviews)
It was a wonderful relaxing stay

Reviewed on Apr 9, 2026

Caesars Windsor - A Caesars Rewards Destination

Caesars Windsor - A Caesars Rewards Destination

4 out of 5
City Centre
Price was $511, price is now $366 per person
$366
per person
Jun 26 - Jun 28
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
8.6/10 Excellent! (3,191 reviews)
Our Stay at Caesars was exceptional! Property was very nice and clean. The room was clean. The bed was very comfortable and the Detroit River view from the 25th floor was great.!

Reviewed on Apr 11, 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 Apr 19 to Apr 20
$92 total
Apr 19 - Apr 20
Total with taxes and fees
8.4/10 Very Good! (1,006 reviews)
The hotel is clean and updated, but I went for the hot tub, which unfortunately was filled with little kids and not hot.

Reviewed on Apr 8, 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 19 to Apr 20
$93 total
Apr 19 - Apr 20
Total with taxes and fees
8.8/10 Excellent! (424 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
$93 nightly
The price is $101 total per night from Apr 26 to Apr 27
$101 total
Apr 26 - Apr 27
Total with taxes and fees
8/10 Very Good! (579 reviews)
The lobby bathrooms were both disgusting. The women’s bathroom was clogged and had toilet paper and paper towel on the floor. The men’s bathroom was not clean either but at least had a flushing toilet. The elevator was also gross. The room was decently clean but the start of the stay was less than ...

Reviewed on Mar 29, 2026

Holiday Inn Express & Suites Chesterfield by IHG
See all 947 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 $164 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.