Chesterfield Vacation Packages 2026 from $584

Chesterfield flight + hotel vacation packages

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

The Wildwood Hotel

Save 100% on your flight

$584

per person

Feb 26 - Mar 3

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Hermann Grain Bins BNB

Save 100% on your flight

$1,093

per person

Mar 4 - Mar 8

found 1 day ago

Roundtrip flight included

Detroit (DTW) to St. Louis (STL)

This bed & breakfast features free WiFi in public areas, barbecue grills, and free self parking. Enjoy the free full breakfast each morning. A garden and a picnic area are also provided.

The Cheshire

$699

per person

Feb 26 - Mar 3

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Hilton Garden Inn Chesterfield

$717

per person

Apr 8 - Apr 13

just found

Roundtrip flight included

Boston (BOS) to St. Louis (STL)

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

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

Grand Center

$749

per person

Feb 26 - Mar 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to St. Louis (STL)

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 6 conference rooms, along with free WiFi in public areas. There's a rooftop terrace on site, and a 24-hour front desk and a snack bar/deli are also provided.

Top Chesterfield hotels deals

Drury Plaza Hotel St. Louis Chesterfield

355 Chesterfield Ctr Chesterfield MO

Get rates

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

$122 nightly

$142 total

Feb 8 - Feb 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

Fairfield Inn & Suites by Marriott St. Louis Chesterfield

1065 Chesterfield Pkwy E Chesterfield MO

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$107 total

Feb 22 - Feb 23

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

Hilton Garden Inn Chesterfield

16631 Chesterfield Grove Ct Chesterfield MO

Free Cancellation

Reserve now, pay when you stay

$88 nightly

$102 total

Feb 1 - Feb 2

Total with taxes and fees

Pool

Pet friendly

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

11 Arnage Boulevard Chesterfield MO

Free Cancellation

$108 nightly

$126 total

Feb 9 - Feb 10

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

21C Museum Hotel St Louis

1528 Locust street St. Louis MO

Free Cancellation

Reserve now, pay when you stay

$148 nightly

$173 total

Feb 22 - Feb 23

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the gym and conveniences like a 24-hour front desk and concierge services.

Pool

Spa

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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 acclaimed art scene or attend a baseball game.

Busch Stadium

Catch an event at Busch Stadium during your trip to St. Louis. Experience the area's great live music 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 $584. 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.