Chesterfield Vacations from $193

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

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

    Find the right fit

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

    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.
American Inn & Suites Waterford

American Inn & Suites Waterford

3 out of 5
Price was $278, price is now $193 per person
$193
per person
Sep 26 - Sep 28
found 6 hours ago
Roundtrip flight included
New York (NYC) to Detroit (DTW)
5.8/10 (1,001 reviews)
The staff were great, the nights were quiet, but the hallway carpets could use a good cleaning.

Reviewed on Aug 3, 2025

Allen Park Motor Lodge

Allen Park Motor Lodge

2.5 out of 5
Save 100% on your flight
Price was $375, price is now $206 per person
$206
per person
Oct 9 - Oct 15
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
7.8/10 Good! (650 reviews)
Everything was good

Reviewed on Aug 4, 2025

Graduate by Hilton Ann Arbor

Graduate by Hilton Ann Arbor

4 out of 5
Kerrytown
Save 100% on your flight
Price was $1,458, price is now $902 per person
$902
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Detroit (DTW)
9/10 Wonderful! (1,006 reviews)
Very nice property close to the university of Michigan. Rooms and bathrooms were small but clean. Nice coffee shop in lobby and staff are friendly. I would however caution you that if you are booking two queen beds in a room they cannot guarantee the bedding. In fact they gave us a king bed instead. There are no rollaway options either. Also if you are a family with multiple rooms they cannot place you adjoining or even on the same floor despite multiple requests so plan accordingly . Probably your best option if visiting Univ of Michigan.

Reviewed on Aug 18, 2025

Weber's Hotel & Restaurant

Weber's Hotel & Restaurant

4 out of 5
Lakewood
Save 100% on your flight
Price was $715, price is now $478 per person
$478
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Detroit (DTW)
9.4/10 Exceptional! (1,302 reviews)
Very friendly and welcoming staff. Room is very clean

Reviewed on Aug 16, 2025

MotorCity Casino Hotel

MotorCity Casino Hotel

4.5 out of 5
North Corktown
Save 100% on your flight
Price was $710, price is now $484 per person
$484
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Detroit (DTW)
8.6/10 Excellent! (3,867 reviews)
Wonderful place to stay

Reviewed on Aug 18, 2025

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

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
$93 nightly
The price is $102 total per night from Aug 31 to Sep 1
$102 total
Aug 31 - Sep 1
Total includes taxes and fees
8.6/10 Excellent! (278 reviews)
"Clean, fresh, excellent."

Reviewed on Aug 16, 2025

Tru by Hilton Chesterfield Township Detroit
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
$101 nightly
The price is $112 total per night from Aug 28 to Aug 29
$112 total
Aug 28 - Aug 29
Total includes taxes and fees
8.4/10 Very Good! (1,005 reviews)
"Spacious clean rooms that are affordable, and am excellent breakfast. The hotel is conveniently placed right off the interstate and plenty to do around Lake St Claire."

Reviewed on Aug 15, 2025

Hampton Inn & Suites Detroit/Chesterfield Township
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 Sep 1 to Sep 2
$112 total
Sep 1 - Sep 2
Total includes taxes and fees
8.6/10 Excellent! (507 reviews)
"The hotel was very clean, comfortable and employees were very kind. They had a good variety of food items during breakfast."

Reviewed on Aug 6, 2025

Fairfield Inn & Suites by Marriott Detroit Chesterfield
See all 889 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.

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 $193 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.