Chesterfield Vacation Packages 2026 from $441

Chesterfield flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Clayton Plaza Hotel & Extended Stay

Clayton

$441

per person

Nov 27 - Nov 29

found 7 hours ago

Roundtrip flight included

Dallas (DFW) to St. Louis (STL)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the sauna and free full breakfast each morning.

Best Western Montis Inn

$596

per person

Dec 15 - Dec 18

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to St. Louis (STL)

This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. A safe deposit box is provided and the front desk is staffed around-the-clock.

Liberty Lounge

$747

per person

Dec 15 - Dec 18

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to St. Louis (STL)

Free WiFi in public areas is available at this apartment. Take advantage of the free self parking.

Fairfield Inn by Marriott Fort Leonard Wood St. Robert

$710

per person

Dec 15 - Dec 18

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to St. Louis (STL)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Bluebird Liberty Cottage

$838

per person

Dec 15 - Dec 18

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to St. Louis (STL)

This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. A computer station, laundry facilities, and barbecue grills are also on offer.

Top Chesterfield hotels deals

Sonesta ES Suites St. Louis - Chesterfield

15431 Conway Rd Chesterfield MO

$99 nightly

$115 total

Nov 8 - Nov 9

Total with taxes and fees

This hotel features a 24-hour gym and a seasonal outdoor pool. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A 24-hour business center, a garden, and express check-out are also on offer.

Pool

Breakfast included

Drury Plaza Hotel St. Louis Chesterfield

355 Chesterfield Ctr Chesterfield MO

$130 nightly

$151 total

Oct 31 - Nov 1

Total with taxes and fees

This hotel features an outdoor pool, an indoor pool, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and free perks like buffet breakfast and free self parking.

Pool

Hot Tub

Hyatt Place St. Louis/Chesterfield

333 Chesterfield Center East Chesterfield MO

Free Cancellation

Reserve now, pay when you stay

$134 nightly

$155 total

Nov 8 - Nov 9

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.

Pool

Breakfast included

Holiday Inn Express & Suites St. Louis - Chesterfield by IHG

11 Arnage Boulevard Chesterfield MO

$105 nightly

$122 total

Nov 1 - Nov 2

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.

Pool

Breakfast included

Pear Tree Inn St. Louis Airport

10810 Pear Tree Ln St. Ann MO

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$106 total

Nov 8 - Nov 9

Total with taxes and fees

This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

Drury Plaza Hotel St. Louis at the Arch

2 South 4th Street St. Louis MO

$144 nightly

$168 total

Nov 1 - Nov 2

Total with taxes and fees

2 hot tubs, an indoor pool, and a gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.

Pool

Hot Tub

Don't see what you're looking for?

See all available properties in Chesterfield

View all properties

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.

Stay near popular Chesterfield attractions

The Factory

8.8/10 (47 reviews)

You can make plans for a show at The Factory on your trip to Chesterfield. Check out the shops and top-notch restaurants in this family-friendly area.

See properties

Frequently asked questions

How much are vacation packages to Chesterfield?

Travelocity has flight and hotel vacation packages from an incredible $441. With such great deals, you'll be exploring all of Chesterfield before you know it.

How long should my Chesterfield vacation be?

There are no rules when it comes to how long you should spend in Chesterfield, but most people opt to stay for around 2 nights. Got some flexibility with your departure date? Consider treating yourself to a couple of extra nights. That way, you'll have loads of time to check out the surrounding areas as well.

Where can I get the best vacation package deals for Chesterfield?

There's no need to look any further than Travelocity. With no less than 400 airlines and 1,000,000 properties around the world, it's a breeze to put together a Chesterfield package deal that suits your travel style.

Why should I book my Chesterfield vacation package with Travelocity?

You'll not only enjoy huge savings, but you'll also have access to our round-the-clock support, quality service and a Price Match Guarantee. Wander across the world, uncover hidden gems and make unforgettable memories — we'll take care of the important details.

Will I save money on my Chesterfield car rental if I combine it with my hotel or flight?

Bundling your bookings into a Chesterfield vacation package will save you some serious money. Book a car and flight; a hotel, flight and car; or a hotel and car. There's no better way to explore the greater Chesterfield area than with your own rental car. You can also add experiences and tours to your Travelocity package.

Which airport is best for Chesterfield?

That would be Lambert-St. Louis Intl. Airport (STL), located 12 mi northeast of central Chesterfield.

What is there to do in Chesterfield?

While hopping off the tourist trail is no doubt rewarding, you shouldn't ignore the well-known sights that make a place famous. St. Louis Premium Outlets and Chesterfield Sports Fusion are just two of them in Chesterfield.

Where should I stay when visiting Chesterfield?

Many people spend their nights at the Drury Plaza Hotel St. Louis Chesterfield. It's sure to be a good base for your Chesterfield vacation.