Chesterfield Vacation Packages 2026 from $176

Chesterfield flight + hotel vacation packages

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

Best Western Plus Fenton

$176

per person

Mar 6 - Mar 8

found 1 day ago

Roundtrip flight included

Orlando (MCO) 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. Free self parking and a computer station are also offered on site.

The Wildwood Hotel

Save 100% on your flight

$214

per person

Mar 6 - Mar 8

found 1 day ago

Roundtrip flight included

Orlando (MCO) 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 Knight Center at Washington University

$226

per person

Mar 6 - Mar 8

found 1 day ago

Roundtrip flight included

Orlando (MCO) to St. Louis (STL)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Self parking and a coffee shop are also offered on site.

Ameristar Casino Resort and Spa

Save 100% on your flight

$338

per person

Mar 6 - Mar 8

found 1 day ago

Roundtrip flight included

Orlando (MCO) to St. Louis (STL)

This luxury hotel features a casino, a full-service spa, and 6 restaurants. Enjoy the 2 hot tubs and 24-hour gym, and unwind with a drink at the poolside bar.

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

Grand Center

$265

per person

Mar 6 - Mar 8

found 1 day ago

Roundtrip flight included

Orlando (MCO) 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

Sonesta ES Suites St. Louis - Chesterfield

15431 Conway Rd Chesterfield MO

Free Cancellation

Reserve now, pay when you stay

$87 nightly

$101 total

Jan 4 - Jan 5, 2026

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 Chesterfield

355 Chesterfield Ctr Chesterfield MO

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$151 total

Jan 1 - Jan 2, 2026

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

$99 nightly

$117 total

Dec 30 - Dec 31

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

Hampton Inn St. Louis-Downtown (At the Gateway Arch)

333 Washington Ave St. Louis MO

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$114 total

Jan 3 - Jan 4, 2026

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 free buffet breakfast each morning.

Magnolia Hotel St. Louis, a Tribute Portfolio Hotel

421 N 8th St St. Louis MO

Free Cancellation

Reserve now, pay when you stay

$97 nightly

$115 total

Jan 25 - Jan 26, 2026

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and a communal living room are also on offer.

Pet friendly

Free WiFi

21C Museum Hotel St Louis

1528 Locust street St. Louis MO

Free Cancellation

Reserve now, pay when you stay

$147 nightly

$172 total

Jan 4 - Jan 5, 2026

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

4/5(615 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 fascinating museums or attend a baseball game.

Busch Stadium

4.5/5(1,469 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.

Gateway Arch

4.5/5(2,511 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 $176. 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.