Chesterfield Vacation Packages 2026 from $444

Chesterfield flight + hotel vacation packages

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

The Cheshire

$444

per person

Jun 9 - Jun 12

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) 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.

The Wildwood Hotel

$1,132

per person

Jun 8 - Jun 14

found 13 hours ago

Roundtrip non-stop flight included

Houston (IAH) 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.

Crowne Plaza St. Louis Airport by IHG

$697

per person

Jun 8 - Jun 14

found 13 hours ago

Roundtrip non-stop flight included

Houston (IAH) to St. Louis (STL)

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

DoubleTree by Hilton St. Louis - Westport

$1,089

per person

Jun 8 - Jun 14

found 13 hours ago

Roundtrip non-stop flight included

Houston (IAH) to St. Louis (STL)

Landing Furnished Apartments - Central West End

Central West End

$873

per person

Jun 8 - Jun 14

found 13 hours ago

Roundtrip non-stop flight included

Houston (IAH) to St. Louis (STL)

This apartment features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, barbecue grills, and a virtual front desk are also on offer.

Top Chesterfield hotels deals

Drury Plaza Hotel St. Louis Chesterfield

355 Chesterfield Ctr Chesterfield MO

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$151 total

Apr 5 - Apr 6

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

Fairfield Inn & Suites by Marriott St. Louis Chesterfield

1065 Chesterfield Pkwy E Chesterfield MO

Free Cancellation

Reserve now, pay when you stay

$118 nightly

$137 total

Apr 12 - Apr 13

Total with taxes and fees

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 buffet breakfast and free self parking.

Pool

Breakfast included

Sonesta ES Suites St. Louis - Chesterfield

15431 Conway Rd Chesterfield MO

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$114 total

Apr 8 - Apr 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 at the Arch

2 South 4th Street St. Louis MO

$156 nightly

$182 total

Apr 7 - Apr 8

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

Pear Tree Inn St. Louis Near Union Station

2211 Market Street St. Louis MO

Free Cancellation

Reserve now, pay when you stay

$113 nightly

$132 total

Apr 13 - Apr 14

Total with taxes and fees

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

Pool

Hot Tub

Clayton Plaza Hotel & Extended Stay

7750 Carondelet Avenue St. Louis MO

Free Cancellation

Reserve now, pay when you stay

$100 nightly

$116 total

Apr 12 - Apr 13

Total with taxes and fees

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.

Pool

Breakfast included

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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.

Popular places to visit

St. Louis Union Station

You can learn about the local history of St. Louis when you make a stop at a well-known site like St. Louis Union Station. Experience the area's great live music or attend a baseball game.

Busch Stadium

Catch an event at Busch Stadium during your trip to St. Louis. Experience the area's acclaimed theater scene or attend a baseball game.

Gateway Arch

Enjoy 360-degree views and learn about the history of St. Louis at this world-famous landmark.

Frequently asked questions

How much are vacation packages to Chesterfield?

Travelocity has flight and hotel vacation packages from an incredible $444. 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.