Chesterfield Vacations from $230

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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 $316, price is now $230 per person
$230
per person
Jun 19 - Jun 21
found 1 day ago
Roundtrip flight included
New York (NYC) to Detroit (DTW)
8/10 Very Good! (1,017 reviews)
Very nice stay for five days. The staff was friendly and quick to respond to any requests. We will definitely stay at Larkspur Landing again when we are in Ann Arbor.

Reviewed on Apr 4, 2026

Hotel Houze Detroit Downtown

Hotel Houze Detroit Downtown

3 out of 5
Downtown Detroit
Price was $788, price is now $477 per person
$477
per person
May 6 - May 10
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Detroit (DTW)
8/10 Very Good! (155 reviews)
The room was amazing for the price! However, we did not have any towels but when we requested them the staff brought them right away. The mattress in the room we stayed in needs to be replaced as there was a huge stain on it. Otherwise bed was comfy and room and everything we needed and more.

Reviewed on Apr 4, 2026

American Inn and Suites Dundee

American Inn and Suites Dundee

2 out of 5
Price was $680, price is now $481 per person
$481
per person
Jun 22 - Jun 27
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Detroit (DTW)
6.8/10 (970 reviews)
The bed was made, front desk was nice. Cleaning people banged on our door promptly at 11.

Reviewed on Oct 27, 2025

MotorCity Casino Hotel

MotorCity Casino Hotel

4.5 out of 5
North Corktown
Price was $1,001, price is now $724 per person
$724
per person
May 6 - May 10
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Detroit (DTW)
8.8/10 Excellent! (4,563 reviews)
The room was dirty found dust and pills. The front desk was rude on two occasions (same employee). Used to be my favorite place to stay in Detroit but has went downhill.

Reviewed on Apr 4, 2026

Saint John's Resort

Saint John's Resort

4 out of 5
Price was $1,652, price is now $1,197 per person
$1,197
per person
Jun 10 - Jun 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Detroit (DTW)
9.6/10 Exceptional! (1,010 reviews)
Had a great time. The resort is beautiful.

Reviewed on Mar 29, 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 12 to Apr 13
$99 total
Apr 12 - Apr 13
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
The ladies in the breakfast area were very nice and helpful. The hotel was under renovation and we stayed on the half that was already "renovated" but it looks like new paint and carpeting although the mattress felt new and that was great!

Reviewed on Apr 3, 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! (423 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
$101 nightly
The price is $110 total per night from Apr 12 to Apr 13
$110 total
Apr 12 - Apr 13
Total with taxes and fees
8/10 Very Good! (578 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 $230 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.