Chesterfield Vacations from $239

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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
Save 100% on your flight
Price was $328, price is now $239 per person
$239
per person
Apr 25 - Apr 27
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
7.8/10 Good! (136 reviews)
We really enjoyed our stay, and will return!

Reviewed on Mar 13, 2026

Graduate by Hilton Ann Arbor

Graduate by Hilton Ann Arbor

4 out of 5
Kerrytown
Save 100% on your flight
Price was $1,689, price is now $1,132 per person
$1,132
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
New York (LGA) to Detroit (DTW)
9/10 Wonderful! (1,005 reviews)
Good location and clean room

Reviewed on Mar 12, 2026

MotorCity Casino Hotel

MotorCity Casino Hotel

4.5 out of 5
North Corktown
Save 100% on your flight
Price was $371, price is now $269 per person
$269
per person
Apr 25 - Apr 27
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
8.8/10 Excellent! (4,579 reviews)
Clean room| staff was amazing and friendly I love the Detroit vibe! | Revel food was amazing!

Reviewed on Mar 15, 2026

The Townsend Hotel

The Townsend Hotel

4 out of 5
Save 100% on your flight
Price was $1,266, price is now $926 per person
$926
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Detroit (DTW)
9.2/10 Wonderful! (719 reviews)
Nice 4.5* hotel ok value for the money in the area. Attentive staff.

Reviewed on Mar 3, 2026

Saint John's Resort

Saint John's Resort

4 out of 5
Save 100% on your flight
Price was $517, price is now $397 per person
$397
per person
Apr 25 - Apr 27
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
9.6/10 Exceptional! (1,006 reviews)
Stayed while in town for a wedding weekend. Loved the gorgeous hotel and grounds, attentive, friendly, front desk staff, and well-appointed quiet room. Would definitely return when I have more time to explore outdoors in warmer weather.

Reviewed on Mar 8, 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! (1,006 reviews)
Under renovation and did not inform (leave notes by elevator the night before) that the elevator was going to be out until 11am on Sunday. Had to carry Sports Equipment and bags down 4 flights of stairs. Pool was available but had to walk outside and walk back inside. Not enough parking due to construction ...

Reviewed on Mar 15, 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
$80 nightly
The price is $88 total per night from Mar 22 to Mar 23
$88 total
Mar 22 - Mar 23
Total with taxes and fees
8.8/10 Excellent! (411 reviews)
My only complaint is the rooms don’t have dressers. Only a few hangers. Everything else was nice.

Reviewed on Mar 15, 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 22 to Mar 23
$110 total
Mar 22 - Mar 23
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 866 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 $239 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.