Chesterfield Vacations from $313

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The Latest Chesterfield vacation packages

Price found within the past 48 hours. Click for updated prices.
Ann Arbor North Inn

Ann Arbor North Inn

2.5 out of 5
Thurston
Save 100% on your flight
Price was $496, price is now $313 per person
$313
per person
Sep 4 - Sep 6
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
7.8/10 Good! (1,017 reviews)
The room was clean. However, overall the hotel is in some state of renovation or updating. It needs it. The breakfast area was closed, no service. Offering coffee 24/7 was not an impressive substitute for the lack of breakfast.

Reviewed on Jul 13, 2026

Weber's Hotel & Restaurant

Weber's Hotel & Restaurant

4 out of 5
Lakewood
Save 100% on your flight
Price was $1,590, price is now $968 per person
$968
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Detroit (DTW)
9.4/10 Exceptional! (1,560 reviews)
And time was had!! Me and my fiancé had a wonderful time!! Everything was beautiful and we slept good!! 10/10 definitely will be back!!

Reviewed on Jul 13, 2026

Saint John's Resort

Saint John's Resort

4 out of 5
Save 100% on your flight
Price was $1,362, price is now $899 per person
$899
per person
Sep 25 - Sep 27
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Detroit (DTW)
9.6/10 Exceptional! (1,002 reviews)
Everything you could get expect.

Reviewed on Jul 11, 2026

Graduate by Hilton Ann Arbor

Graduate by Hilton Ann Arbor

4 out of 5
Kerrytown
Save 100% on your flight
Price was $2,065, price is now $1,444 per person
$1,444
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Detroit (DTW)
9/10 Wonderful! (1,000 reviews)
Cute hotel. Close to UMich Campus and restaurants.

Reviewed on Jul 13, 2026

Executive Downtown Retreat

Executive Downtown Retreat

4 out of 5
Downtown Detroit
Save 100% on your flight
Price was $1,308, price is now $979 per person
$979
per person
Sep 17 - Sep 22
found 22 hours ago
Roundtrip flight included
Philadelphia (PHL) to Detroit (DTW)
9.4/10 Exceptional! (31 reviews)
It’s definitely an apartment with a wroth it price.

Reviewed on Jul 7, 2026

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Chesterfield Hotel Deals

Fairfield Inn & Suites by Marriott Detroit Chesterfield

Fairfield Inn & Suites by Marriott Detroit Chesterfield

3 out of 5
45800 Market Place Blvd New Baltimore MI
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $102 total per night from Jul 21 to Jul 22
$102 total
Jul 21 - Jul 22
Total with taxes and fees
8.8/10 Excellent! (585 reviews)
"Breakfast was poor in variety"

Reviewed on Jul 8, 2026

Fairfield Inn & Suites by Marriott Detroit Chesterfield
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
$98 nightly
The price is $108 total per night from Jul 26 to Jul 27
$108 total
Jul 26 - Jul 27
Total with taxes and fees
8.4/10 Very Good! (1,002 reviews)
"Clean room nice mattress breakfast not to bad"

Reviewed on Jul 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
$98 nightly
The price is $108 total per night from Aug 9 to Aug 10
$108 total
Aug 9 - Aug 10
Total with taxes and fees
8.8/10 Excellent! (465 reviews)
"Good staff and clean rooms"

Reviewed on Jul 13, 2026

Tru by Hilton Chesterfield Township Detroit
See all 921 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 $313 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.