Chesterfield Vacations from $315
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The Latest Chesterfield Vacation Packages
- Trumbull and Porter Hotel
Sep 25 - Sep 27Trumbull and Porter Hotel + Flight
Corktown2 nights3.5 star property8.4/10 - Very Good (1,220 reviews)"Room was not very clean after being told the supervisor needed to approve the cleaning in a several step process during check in. Floor in room was sticky. Decorative pillow on chair had a stain. Shower floor looked unclean with dirty grout and the room smelled like dirty mop water. The sheets seemed clean. Checked out less then 30 minutes after checking in and was told to contact expedia for a refund. They then reached out to the property with no response. Was asked to contact expedia another..."Reviewed August 3, 2026Roundtrip • Atlanta (ATL) - Detroit (DTW)ATL - DTW • Nonstop DTW - ATL • Nonstop - Saint John's Resort
Sep 4 - Sep 7Saint John's Resort + Flight
Plymouth3 nights4.0 star property9.6/10 - Exceptional (1,005 reviews)"The property is gorgeous & well maintained. If you’ve never been to the grounds it is hard to find restaurants due to lack of signage. I would definitely go back in hopes of getting a room with a patio."Reviewed August 2, 2026Roundtrip • Atlanta (ATL) - Detroit (DTW)ATL - DTW • Nonstop DTW - ATL • Nonstop - The Townsend Hotel
Sep 4 - Sep 7The Townsend Hotel + Flight
Birmingham3 nights4.0 star property9.2/10 - Wonderful (780 reviews)Roundtrip • Atlanta (ATL) - Detroit (DTW)ATL - DTW • Nonstop DTW - ATL • Nonstop - Ann Arbor North Inn
Sep 4 - Sep 7Ann Arbor North Inn + Flight
Thurston3 nights2.5 star property7.8/10 - Good (1,059 reviews)"Place was very dirty and dated, no free breakfast or pool."Reviewed August 2, 2026Roundtrip • Atlanta (ATL) - Detroit (DTW)ATL - DTW • Nonstop DTW - ATL • Nonstop - Weber's Hotel & Restaurant
Oct 14 - Oct 17Weber's Hotel & Restaurant + Flight
Lakewood3 nights4.0 star property9.4/10 - Exceptional (1,563 reviews)"Great service Modern room"Reviewed August 3, 2026Roundtrip • Dallas (DFW) - Detroit (DTW)DFW - DTW • Nonstop DTW - DFW • Nonstop
Chesterfield Hotel Deals
Tru by Hilton Chesterfield Township Detroit
Tru by Hilton Chesterfield Township Detroit
Fairfield Inn & Suites by Marriott Detroit Chesterfield
Fairfield Inn & Suites by Marriott Detroit Chesterfield
TownePlace Suites by Marriott Chesterfield
TownePlace Suites by Marriott Chesterfield
Holiday Inn Express & Suites Chesterfield by IHG
Holiday Inn Express & Suites Chesterfield by IHG
Holiday Inn Express and Suites Detroit/Sterling Heights by IHG
Holiday Inn Express and Suites Detroit/Sterling Heights by IHG
Cambria Hotel Shelby Township - Detroit Utica
Cambria Hotel Shelby Township - Detroit Utica
Candlewood Suites Detroit Sterling Heights by IHG
Candlewood Suites Detroit Sterling Heights by IHGFrequently Asked Questions
How much does a Chesterfield vacation package cost?
Offering great value package deals from $315 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.