Chesterfield Vacation Packages 2026 from $507

Chesterfield flight + hotel vacation packages

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

The Principal Hotel

$507

per person

Jul 10 - Jul 14

found 1 day ago

Roundtrip flight included

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

A restaurant and a gym are featured at this hotel. Free self parking, a coffee shop, and dry cleaning are also offered.

The Wildwood Hotel

Save 100% on your flight

$700

per person

Jun 15 - Jun 20

found 9 hours ago

Roundtrip non-stop flight included

New York (JFK) 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 Royal Sonesta Chase Park Plaza St. Louis

Central West End

Save 100% on your flight

$1,129

per person

Jun 14 - Jun 18

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to St. Louis (STL)

This luxury hotel features 3 restaurants, a bar/lounge, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the seasonal outdoor pool, poolside bar, and concierge services.

Alhonna Resort LLC

$713

per person

Jul 18 - Jul 21

found 1 hour ago

Roundtrip non-stop flight included

Palm Springs (PSP) 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.

Spacious 3-Bedroom with King Bed

Central West End

$656

per person

Jul 27 - Jul 29

found 1 day ago

Roundtrip flight included

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

This apartment doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, laundry facilities, 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

$129 nightly

$150 total

May 21 - May 22

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

May 31 - Jun 1

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

Sonesta ES Suites St. Louis - Chesterfield

15431 Conway Rd Chesterfield MO

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$117 total

May 21 - May 22

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

Hyatt Regency St. Louis at The Arch

315 Chestnut St St. Louis MO

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$149 total

May 25 - May 26

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

Hollywood Casino & Hotel St. Louis

777 Casino Center Drive Maryland Heights MO

Free Cancellation

Reserve now, pay when you stay

$116 nightly

$136 total

Jun 1 - Jun 2

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.

Free airport shuttle

Parking included

Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

1088 South Highway Drive Fenton MO

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$103 total

May 18 - May 19

Total with taxes and fees

This hotel features an outdoor pool and an indoor pool. 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

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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

Busch Stadium

4.5/5(1,487 reviews)

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

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 great live music or attend a baseball game.

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 $507. 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.