Chesterfield Vacation Packages 2026 from $439

Chesterfield flight + hotel vacation packages

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

The Cheshire

Save 100% on your flight

$439

per person

Oct 2 - Oct 5

found 7 hours ago

Roundtrip flight included

Denver (DEN) 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.

Remodeled and Inviting Free EV

Save 100% on your flight

$852

per person

Sep 17 - Sep 23

found 4 hours ago

Roundtrip flight included

New York (NYC) to St. Louis (STL)

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A virtual front desk are provided for your convenience.

Residence Inn by Marriott St Louis Downtown

Midtown

$608

per person

Sep 21 - Sep 25

found 15 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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. Self parking, a terrace, and a grocery/convenience store are also offered.

The Wildwood Hotel

$558

per person

Sep 10 - Sep 13

found 15 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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.

Residence Inn by Marriott St. Louis West County

Save 100% on your flight

$657

per person

Oct 3 - Oct 10

found 1 day ago

Roundtrip flight included

Denver (DEN) to St. Louis (STL)

This hotel features an indoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the free full breakfast each morning.

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

Aug 1 - Aug 2

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 Regency St. Louis at The Arch

315 Chestnut St St. Louis MO

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$179 total

Jul 31 - Aug 1

Total with taxes and fees

This smoke-free hotel's 3 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a rooftop terrace on site, and a 24-hour front desk and a coffee shop are also provided.

Pet friendly

Free WiFi

Clayton Plaza Hotel & Extended Stay

7750 Carondelet Avenue St. Louis MO

Free Cancellation

Reserve now, pay when you stay

$97 nightly

$113 total

Aug 9 - Aug 10

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

Hollywood Casino & Hotel St. Louis

777 Casino Center Drive Maryland Heights MO

Free Cancellation

Reserve now, pay when you stay

$142 nightly

$166 total

Aug 2 - Aug 3

Total with taxes and fees

A casino, 7 restaurants, and a 24-hour gym are all featured at this hotel. Traveling on business? Take advantage of the 24-hour business center, express check-out, and free airport shuttle. Relax with a drink at one of the 3 bars/lounges and enjoy perks like free self parking.

Renaissance St. Louis Airport Hotel

9801 Natural Bridge Road St. Louis MO

Free Cancellation

Reserve now, pay when you stay

$115 nightly

$135 total

Aug 9 - Aug 10

Total with taxes and fees

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, laundry service, and free airport shuttle. You'll appreciate the seasonal outdoor pool, bar/lounge, and laundry facilities.

Pool

Free airport shuttle

Drury Plaza Hotel St. Louis at the Arch

2 South 4th Street St. Louis MO

Free Cancellation

Reserve now, pay when you stay

$153 nightly

$179 total

Aug 3 - Aug 4

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

St. Louis Premium Outlets

8.8/10 (369 reviews)

You can enjoy retail therapy at St. Louis Premium Outlets during your stay in Chesterfield. Discover the top-notch restaurants and great live music 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 $439. 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.