Chesterfield Vacation Packages 2026 from $372

Chesterfield flight + hotel vacation packages

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

The Wildwood Hotel

$372

per person

Jan 8 - Jan 11

found 4 hours ago

Roundtrip flight included

Charlotte (CLT) to St. Louis (STL)

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. Enjoy the hot tub and free perks like continental breakfast and free self parking.

The Cheshire

$590

per person

Jan 28 - Feb 1

found 1 hour ago

Roundtrip non-stop flight included

Seattle (SEA) to St. Louis (STL)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and free English breakfast each morning.

Ameristar Casino Resort and Spa

$642

per person

Jan 28 - Feb 1

found 1 hour ago

Roundtrip non-stop flight included

Seattle (SEA) to St. Louis (STL)

This luxury hotel features a casino, a full-service spa, and 6 restaurants. Enjoy the 2 hot tubs and outdoor pool, and unwind with a drink at the poolside bar.

Country Inn & Suites by Radisson, St. Charles Historic District

St. Charles Historic District

$379

per person

Jan 8 - Jan 11

found 4 hours ago

Roundtrip flight included

Charlotte (CLT) to St. Louis (STL)

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

Larkspur Landing Extended Stay Suites St. Louis Riverport - Airport West

Riverport

$435

per person

Jan 28 - Feb 1

found 1 hour ago

Roundtrip non-stop flight included

Seattle (SEA) 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. Guests will appreciate freebies like continental breakfast and free self parking.

Top Chesterfield hotels deals

Sonesta ES Suites St. Louis - Chesterfield

15431 Conway Rd Chesterfield MO

Free Cancellation

Reserve now, pay when you stay

$97 nightly

$112 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

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$151 total

Nov 8 - Nov 9

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

$139 nightly

$161 total

Nov 4 - Nov 5

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

Free Cancellation

$110 nightly

$128 total

Nov 19 - Nov 20

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

Free Cancellation

Reserve now, pay when you stay

$144 nightly

$168 total

Nov 9 - Nov 10

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

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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 $372. 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.