Chesterfield Vacations from $367

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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 $530, price is now $367 per person
$367
per person
Jul 20 - Jul 23
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
8/10 Very Good! (324 reviews)
The room was nice and spacious. Having the full kitchen was a huge bonus. Nicely located and the staff was friendly for check in.

Reviewed on May 16, 2026

Saint John's Resort

Saint John's Resort

4 out of 5
Save 100% on your flight
Price was $919, price is now $553 per person
$553
per person
Jul 11 - Jul 13
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
9.6/10 Exceptional! (1,006 reviews)
Did not have Breakfast

Reviewed on May 15, 2026

The Townsend Hotel

The Townsend Hotel

4 out of 5
Save 100% on your flight
Price was $792, price is now $514 per person
$514
per person
Jul 20 - Jul 23
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
9.2/10 Wonderful! (748 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 $738, price is now $501 per person
$501
per person
Jul 20 - Jul 23
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
9.4/10 Exceptional! (1,560 reviews)
Loved the pool, sauna, hot tub and small arcade room! Bed was extremely comfortable. Toilet seat was heated which was cool! Didnt use shower, but looked great. Also meant to stop at the habitat lounge on site from 9p to 11p for live jazz music, but feel asleep in comfy bed!

Reviewed on May 15, 2026

Daxton Hotel Birmingham, Curio Collection by Hilton

Daxton Hotel Birmingham, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $1,430, price is now $1,073 per person
$1,073
per person
Jul 20 - Jul 23
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
9.2/10 Wonderful! (573 reviews)
Great location and fantastic Hotel.

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 Jun 2 to Jun 3
$92 total
Jun 2 - Jun 3
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
Enjoyed my stay

Reviewed on May 12, 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
$93 nightly
The price is $102 total per night from May 24 to May 25
$102 total
May 24 - May 25
Total with taxes and fees
8.8/10 Excellent! (439 reviews)
Everything was top notch and staff was very friendly and accommodating. Best hotel experience ever!

Reviewed on May 16, 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
$114 nightly
The price is $124 total per night from May 21 to May 22
$124 total
May 21 - May 22
Total with taxes and fees
8/10 Very Good! (588 reviews)
Not the best location if you wish to go for a run in the morning. Heavy traffic but safe.

Reviewed on May 15, 2026

Holiday Inn Express & Suites Chesterfield by IHG
See all 945 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 $367 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.