Chesterfield Vacations from $256

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The Latest Chesterfield vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Royal Oak

Hotel Royal Oak

3 out of 5
Price was $371, price is now $256 per person
$256
per person
Jan 18 - Jan 21
found 1 day ago
Roundtrip flight included
New York (NYC) to Detroit (DTW)
8.6/10 Excellent! (1,010 reviews)
Nice lil place, clean and decent. Close to downtown and a great little breakfast joint right next door. Comfy bed, friendly staff:)

Reviewed on Nov 2, 2025

Saint John's Resort

Saint John's Resort

4 out of 5
Price was $777, price is now $552 per person
$552
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Detroit (DTW)
9.6/10 Exceptional! (1,002 reviews)
Very lovely hotel! Friendly staff, great food and my kids loved the unique pool. We’ll definitely stay here again.

Reviewed on Nov 3, 2025

MotorCity Casino Hotel

MotorCity Casino Hotel

4.5 out of 5
North Corktown
Price was $1,006, price is now $745 per person
$745
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Detroit (DTW)
8.8/10 Excellent! (4,196 reviews)
The desk lamp was broken. The staff at the front desk were very friendly and helpful.

Reviewed on Nov 3, 2025

Frederick Stearns House Historic Inn

Frederick Stearns House Historic Inn

4.5 out of 5
West Village
Save 100% on your flight
Price was $561, price is now $421 per person
$421
per person
Jan 18 - Jan 21
found 1 day ago
Roundtrip flight included
New York (NYC) to Detroit (DTW)
9.6/10 Exceptional! (124 reviews)
Staff/owner was great to let us check in early.

Reviewed on Oct 27, 2025

The Inn on Ferry Street

The Inn on Ferry Street

3.5 out of 5
Cultural Center
Price was $359, price is now $271 per person
$271
per person
Jan 18 - Jan 21
found 1 day ago
Roundtrip flight included
New York (NYC) to Detroit (DTW)
9.4/10 Exceptional! (1,004 reviews)
Attentive staff. Good fresh fruit and variety.

Reviewed on Nov 3, 2025

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Chesterfield Hotel Deals

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
$81 nightly
The price is $90 total per night from Nov 30 to Dec 1
$90 total
Nov 30 - Dec 1
Total with taxes and fees
8.6/10 Excellent! (330 reviews)
We frequently travel to this area and this is our go to spot for a quiet comfortable stay.

Reviewed on Oct 27, 2025

Tru by Hilton Chesterfield Township Detroit
Fairfield Inn & Suites by Marriott Detroit Chesterfield

Fairfield Inn & Suites by Marriott Detroit Chesterfield

2.5 out of 5
45800 Market Place Blvd, New Baltimore, MI
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $112 total per night from Nov 16 to Nov 17
$112 total
Nov 16 - Nov 17
Total with taxes and fees
8.6/10 Excellent! (532 reviews)
Compared to other chains, the oatmeal was very thick, only option of fresh fruit was oranges

Reviewed on Oct 31, 2025

Fairfield Inn & Suites by Marriott Detroit Chesterfield
TownePlace Suites by Marriott Chesterfield

TownePlace Suites by Marriott Chesterfield

3 out of 5
45255 Marketplace Blvd., Chesterfield, New Baltimore, MI
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $135 total per night from Nov 30 to Dec 1
$135 total
Nov 30 - Dec 1
Total with taxes and fees
9.2/10 Wonderful! (157 reviews)
Yes

Reviewed on Oct 26, 2025

TownePlace Suites by Marriott Chesterfield
See all 930 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 $256 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.