Chesterfield Vacations from $341

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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
Price was $520, price is now $341 per person
$341
per person
May 7 - May 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
8/10 Very Good! (155 reviews)
LOVED my stay here, will be back for every Detroit trip.

Reviewed on Mar 24, 2026

The Townsend Hotel

The Townsend Hotel

4 out of 5
Price was $730, price is now $500 per person
$500
per person
May 7 - May 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
9.2/10 Wonderful! (719 reviews)
Racism abounds!! The front desk staff were only too eager to place my husband and I in inferior rooms when we arrived. I had to aggressively self advocate as a woman of colour (and the one paying the tab!) for a room on the top floor! The hotel decor is nice but dated… lots of dark browns and beiges…. The cafe front staff was disrespectful and condescending. We waited more than five minutes to be acknowledged. They whispered to each other for a couple minutes then without even a “good day” one of them said “come with me”. The entire town was like this… I was happy when we were across the border and back in Canada!

Reviewed on Mar 27, 2026

MotorCity Casino Hotel

MotorCity Casino Hotel

4.5 out of 5
North Corktown
Price was $757, price is now $559 per person
$559
per person
May 7 - May 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
8.8/10 Excellent! (4,563 reviews)
Clean room friendly staff! Always enjoy my stay here at MotorCity my #1 choice of places to stay in detroit.

Reviewed on Mar 28, 2026

Saint John's Resort

Saint John's Resort

4 out of 5
Price was $927, price is now $726 per person
$726
per person
May 7 - May 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
9.6/10 Exceptional! (1,010 reviews)
Had a great time. The resort is beautiful.

Reviewed on Mar 29, 2026

Trumbull and Porter Hotel

Trumbull and Porter Hotel

3.5 out of 5
Corktown
Save 100% on your flight
Price was $900, price is now $705 per person
$705
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Detroit (DTW)
8.2/10 Very Good! (1,019 reviews)
Everything was great. In particular, I want to highlight the staff. I ran into a problem with my phone charger, and one staff member went far out of her way to help me, saving me a lot of trouble. I’ll always be grateful for that extra kindness and am glad I chose Trumbull and Porter.

Reviewed on Mar 29, 2026

Don't see what you're looking for?
See all available trips from Columbus to Chesterfield
View all trips

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 5 to Apr 6
$99 total
Apr 5 - Apr 6
Total with taxes and fees
8.4/10 Very Good! (1,003 reviews)
The breakfast was uneatable as it was ice cold. We were concerned as we were unsure how long it was sitting out unheated

Reviewed on Mar 29, 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 5 to Apr 6
$93 total
Apr 5 - Apr 6
Total with taxes and fees
8.8/10 Excellent! (421 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 5 to Apr 6
$110 total
Apr 5 - Apr 6
Total with taxes and fees
8/10 Very Good! (577 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Chesterfield vacation package cost?
Offering great value package deals from $341 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.