Chesterfield Vacation Packages 2026 from $444

Chesterfield flight + hotel vacation packages

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

Lodge Of Four Seasons Golf Resort, Marina & Spa

$444

per person

Sep 3 - Sep 6

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to St. Louis (STL)

This resort features a golf course, a full-service spa, and a marina. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. You'll find 2 restaurants and 5 bars/lounges for dining and drinks, and an indoor pool is also on site.

The Wildwood Hotel

Save 100% on your flight

$554

per person

Sep 3 - Sep 6

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) 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.

Alhonna Resort LLC

$545

per person

Aug 13 - Aug 16

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) 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.

Camden on the Lake Resort & Spa

$613

per person

Sep 3 - Sep 6

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) 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.

Ameristar Casino Resort and Spa

$616

per person

Sep 3 - Sep 6

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) 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

Sonesta ES Suites St. Louis - Chesterfield

15431 Conway Rd Chesterfield MO

Free Cancellation

Reserve now, pay when you stay

$126 total

per night

Jul 19 - Jul 20

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

$158 total

per night

Jul 8 - Jul 9

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

$165 total

per night

Jul 17 - Jul 18

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

$112 total

per night

Jul 12 - Jul 13

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

Pear Tree Inn St. Louis Airport

10810 Pear Tree Ln St. Ann MO

Free Cancellation

Reserve now, pay when you stay

$106 total

per night

Jul 12 - Jul 13

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.

Pool

Breakfast included

Forest Park Hotel by MDR

5915 Wilson Ave St. Louis MO

Free Cancellation

Reserve now, pay when you stay

$103 total

per night

Jul 6 - Jul 7

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling for business? Take advantage of the 24-hour business center, express check-out, and conference space. A seasonal outdoor pool is on site, and free parking and a 24-hour front desk are also offered.

Pool

Pet friendly

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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.

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 $444. 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.