Chesterfield Vacations from $276

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.
Larkspur Landing Ann Arbor

Larkspur Landing Ann Arbor

2.5 out of 5
Thurston
Price was $364, price is now $276 per person
$276
per person
Jun 5 - Jun 7
found 9 hours ago
Roundtrip flight included
Philadelphia (PHL) to Detroit (DTW)
8/10 Very Good! (1,017 reviews)
Got in late. Staff at desk was very pleasant and helpful. Only bummer was no blanket or top sheet available for pullout couch. Staff did try to find one but didnt. Room and bathroom very clean. Morning staff not so great. Kitchen/ food service worker not interested in making eggs or meat options after 8:30 though open unt 10:00. Juice dispenser broken. No fridge items ( yogurt etc.) Only high carb options available.

Reviewed on Mar 29, 2026

Hotel Houze Detroit Downtown

Hotel Houze Detroit Downtown

3 out of 5
Downtown Detroit
Price was $388, price is now $277 per person
$277
per person
Jun 19 - Jun 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
8/10 Very Good! (155 reviews)
Very nice room with a fully equipped kitchen and washer and dryer inside. Great atmosphere and very friendly staff!

Reviewed on Mar 31, 2026

Ann Arbor Marriott Ypsilanti at Eagle Crest

Ann Arbor Marriott Ypsilanti at Eagle Crest

4 out of 5
Price was $670, price is now $521 per person
$521
per person
Jun 9 - Jun 14
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Detroit (DTW)
8.6/10 Excellent! (588 reviews)
Great for meetings and gathering.

Reviewed on Mar 24, 2026

Staybridge Suites Ann Arbor- Univ of Michigan by IHG

Staybridge Suites Ann Arbor- Univ of Michigan by IHG

3 out of 5
Bryant Pattengill East
Save 100% on your flight
Price was $684, price is now $537 per person
$537
per person
May 7 - May 12
found 1 day ago
Roundtrip flight included
New York (NYC) to Detroit (DTW)
8.8/10 Excellent! (606 reviews)
Clean rooms, fully equipped kitchen, friendly staff.

Reviewed on Mar 25, 2026

DoubleTree by Hilton Detroit - Dearborn

DoubleTree by Hilton Detroit - Dearborn

4 out of 5
Warrendale
Price was $392, price is now $310 per person
$310
per person
Jun 19 - Jun 21
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Detroit (DTW)
8/10 Very Good! (1,002 reviews)
The room was acceptably clean, no breakfast offered with room, and the pool was overrun with a rowdy group who were grossly overstaying their numbers allowed to rooms (no fault of the hotel) causing management to close the pool. The lobby and hallways were kept nice and smelled pleasant. Overall a good stay, less the group of 50 or so rowdy guests whose children were unsupervised at the pool.

Reviewed on Mar 23, 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 9 to Apr 10
$99 total
Apr 9 - Apr 10
Total with taxes and fees
8.4/10 Very Good! (1,000 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 19 to Apr 20
$93 total
Apr 19 - Apr 20
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 12 to Apr 13
$110 total
Apr 12 - Apr 13
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 $276 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.