Chesterfield Vacation Packages 2026 from $370

Chesterfield flight + hotel vacation packages

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

Alhonna Resort LLC

$370

per person

Sep 8 - Sep 11

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to St. Louis (STL)

This resort features a private beach, a marina, and a restaurant. Enjoy the indoor pool and perks like free self parking and free WiFi. You'll appreciate the seasonal outdoor pool, bar/lounge, and laundry facilities.

The Wildwood Hotel

Save 100% on your flight

$529

per person

Sep 18 - Sep 21

found 16 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.

Camden on the Lake Resort & Spa

$709

per person

Aug 19 - Aug 23

found 9 hours ago

Roundtrip flight included

Phoenix (PHX) to St. Louis (STL)

This smoke-free resort features a full-service spa, a marina, and 2 restaurants. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the 2 hot tubs and get free self parking.

The Cheshire

$454

per person

Sep 8 - Sep 11

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) 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

$521

per person

Sep 8 - Sep 11

found 7 hours ago

Roundtrip flight included

Philadelphia (PHL) 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.

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

Jul 5 - Jul 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.

Hyatt Regency St. Louis at The Arch

315 Chestnut St St. Louis MO

Free Cancellation

Reserve now, pay when you stay

$149 nightly

$175 total

Jul 17 - Jul 18

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.

Clayton Plaza Hotel & Extended Stay

7750 Carondelet Avenue St. Louis MO

Free Cancellation

Reserve now, pay when you stay

$96 nightly

$112 total

Jul 12 - Jul 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.

Hollywood Casino & Hotel St. Louis

777 Casino Center Drive Maryland Heights MO

$116 nightly

$136 total

Jun 30 - Jul 1

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.

Pear Tree Inn St. Louis Airport

10810 Pear Tree Ln St. Ann MO

Free Cancellation

Reserve now, pay when you stay

$90 nightly

$106 total

Jul 6 - Jul 7

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.

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

Jul 5 - Jul 6

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.

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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

A historic building with a clock tower and red-roofed structures.

St. Louis Union Station

4/5(625 reviews)

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.

A baseball stadium with a large crowd, a prominent arch structure, and various advertisements.

Busch Stadium

4.5/5(1,487 reviews)

Catch an event at Busch Stadium during your trip to St. Louis. Experience the area's great live music or attend a baseball game.

A city skyline with a prominent arch structure.

Gateway Arch

4.5/5(2,542 reviews)

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 $370. 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.