Title: Chesterfield Vacation Packages & Trips 2026 from CA $762 | Expedia.ca

[Chesterfield Travel Guide](https://expedia.ca/Chesterfield.dx9530)[Hotels in Chesterfield](https://expedia.ca/Chesterfield-Hotels.d9530.Travel-Guide-Hotels)[Vacation Rentals in Chesterfield](https://expedia.ca/Chesterfield-Vacation-Rentals.d9530.Travel-Guide-VacationRentals)[Flights to Chesterfield](https://expedia.ca/Cheap-Flights-To-Chesterfield.d9530.Travel-Guide-Flights)[Things to do in Chesterfield](https://expedia.ca/Things-To-Do-In-Chesterfield.d9530.Travel-Guide-Activities)[Chesterfield Car Rentals](https://expedia.ca/Car-Rentals-In-Chesterfield.d9530.Car-Rental-Guide)

![](https://images.trvl-media.com/place/9530/c6d3b4d9-41bc-4a55-9787-aa13d1650621.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Chesterfield Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

#### Your Chesterfield Vacation

Let our vacation packages to Chesterfield inspire your next great escape. There's a whole lot to love about this amazing city, starting with the neighborhood of Valley Park, which is great for golfing and nature. Make your trip to Chesterfield even more enjoyable by going sightseeing. [St. Louis Premium Outlets](https://www.expedia.ca/St-Louis-Premium-Outlets-St-Louis.d553248621561876860.Vacation-Attraction), [Lou Fusz Soccer Complex](https://www.expedia.ca/Lou-Fusz-Soccer-Complex-St-Louis.d553248635975913244.Vacation-Attraction) and [Westfield Chesterfield Mall](https://www.expedia.ca/Westfield-Chesterfield-Mall-St-Louis.d6190516.Vacation-Attraction) are some of the leading attractions worth exploring. Whatever your travel plans or budget, organizing a tailored Chesterfield vacation is a cinch with Expedia.

## Top Chesterfield Vacation Deals

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

![The Eagles Nest Inn](https://images.trvl-media.com/lodging/112000000/111950000/111944700/111944656/9536012a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Eagles Nest Inn

CA $762

per person

May 8 - May 11

found 24 hours ago

Roundtrip flight included

Toronto (YYZ) to St. Louis (STL)

9.4/10 Exceptional! (18 reviews)

Room was spacious and clean. Had a great stay. The restaurant was delicious.

Reviewed on Jan 16, 2026

![The Cheshire](https://images.trvl-media.com/lodging/1000000/30000/26100/26061/b6ec06de_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Cheshire

CA $1,554

per person

Mar 17 - Mar 23

found 1 day ago

Roundtrip flight included

Kelowna (YLW) to St. Louis (STL)

8.6/10 Excellent! (1,002 reviews)

I love the whole "English Tudor" vibe at the hotel. The room was clean and well-appointed. The staff is friendly and the hotel lounge is a fun place to unwind.

Reviewed on Feb 6, 2026

![Hilton Garden Inn Chesterfield](https://images.trvl-media.com/lodging/1000000/300000/297100/297075/c23cebe0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Garden Inn Chesterfield

CA $1,550

per person

Mar 17 - Mar 23

found 1 day ago

Roundtrip flight included

Kelowna (YLW) to St. Louis (STL)

8.2/10 Very Good! (779 reviews)

Staff was informative during check-in. Room was clean and the TV even had WELCOME with my name on it. Would stay here again.

Reviewed on Dec 22, 2025

![Riverside Inn Hannibal](https://images.trvl-media.com/lodging/38000000/37180000/37171800/37171765/68b34759_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Riverside Inn Hannibal

CA $939

per person

May 8 - May 11

found 24 hours ago

Roundtrip flight included

Toronto (YYZ) to St. Louis (STL)

9.4/10 Exceptional! (162 reviews)

Clean, spacious room with a big desk; fully functional kitchen (full size fridge, stove, dishwasher, dishes, pots and pans); large walk-in shower; and comfortable bed. Quiet (unlike larger chain hotels). Great view of the river. Delicious Mexican food downstairs. 11/10, will stay here again.

Reviewed on Nov 23, 2025

![Lighthouse Inn & Suites](https://images.trvl-media.com/lodging/106000000/105130000/105120300/105120258/fb550013_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Lighthouse Inn & Suites

CA $941

per person

May 8 - May 11

found 24 hours ago

Roundtrip flight included

Toronto (YYZ) to St. Louis (STL)

8.8/10 Excellent! (23 reviews)

Nice room. Matched the pictures. Exactly what we were looking for.

Reviewed on Jan 18, 2026

## Ready to book your vacation to Chesterfield?

Choose your dates

## Chesterfield Hotel Deals

![Drury Plaza Hotel St. Louis Chesterfield](https://images.trvl-media.com/lodging/2000000/1350000/1346800/1346760/c1fcfc39_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Drury Plaza Hotel St. Louis Chesterfield

355 Chesterfield Ctr Chesterfield MO

Fully refundableReserve now, pay when you stay

CA $176

CA $204 total

Feb 15 - Feb 16

includes taxes & fees

9.6/10 Exceptional! (1,060 reviews)

Very clean. Fresh food

Reviewed on Feb 2, 2026

[](https://expedia.ca/Hotel-Search?startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&selected=1346760&PinnedHotelID=1346760&HadPinnedHotel=true&regionId=9530)

![Fairfield Inn & Suites by Marriott St. Louis Chesterfield](https://images.trvl-media.com/lodging/1000000/130000/126800/126794/b774ae26_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Fairfield Inn & Suites by Marriott St. Louis Chesterfield

1065 Chesterfield Pkwy E Chesterfield MO

Fully refundableReserve now, pay when you stay

CA $131

CA $152 total

Feb 22 - Feb 23

includes taxes & fees

9/10 Wonderful! (1,000 reviews)

Good

Reviewed on Jan 28, 2026

[](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=126794&PinnedHotelID=126794&HadPinnedHotel=true&regionId=9530)

![Hilton Garden Inn Chesterfield](https://images.trvl-media.com/lodging/1000000/300000/297100/297075/c23cebe0_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hilton Garden Inn Chesterfield

16631 Chesterfield Grove Ct Chesterfield MO

Fully refundableReserve now, pay when you stay

CA $140

CA $163 total

Feb 22 - Feb 23

includes taxes & fees

8.2/10 Very Good! (791 reviews)

Great hotel

Reviewed on Jan 18, 2026

[](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=297075&PinnedHotelID=297075&HadPinnedHotel=true&regionId=9530)

[See all 2,170 properties in Chesterfield](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=11%2F02%2F2026&endDate=12%2F02%2F2026&regionId=9530)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### Discover the most popular places to visit in Chesterfield

![St. Louis Cardinals Baseball. ](https://images.trvl-media.com/place/3284/67189e41-0060-455b-85a9-ab65c9125a63.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Busch Stadium

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

[](https://expedia.ca/Busch-Stadium-Downtown-St-Louis.d502872.Vacation-Attraction)

![Gateway Arch featuring modern architecture, a city and a skyscraper](https://images.trvl-media.com/place/502855/34e3411a-eeba-4fa1-95fe-3ad9b54938f4.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Gateway Arch

Enjoy 360-degree views and learn about the history of St. Louis at this world-famous landmark.

[](https://expedia.ca/Gateway-Arch-Downtown-St-Louis.d502855.Vacation-Attraction)

![St. Louis Zoo](https://images.trvl-media.com/place/502878/51adfd0a-5175-4aa9-aa40-2221835ea3ae.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### St. Louis Zoo

In the middle of St. Louis, meet the exotic and endangered animals that live in meticulously recreated ecosystems from all over the world.

[](https://expedia.ca/St-Louis-Zoo-St-Louis.d502878.Vacation-Attraction)

### What to do in Chesterfield

![St Louis Self-Guided Driving and Walking Audio Tour](https://mediaim.expedia.com/localexpert/49269846/95dbaecc-d0df-4a0c-a007-7dc95eddf58f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### St Louis Self-Guided Driving and Walking Audio Tour

CA $23

per traveller

[](https://expedia.ca/things-to-do/st-louis-self-guided-driving-and-walking-audio-tour.a49269846.activity-details)

![St. Louis: Gateway Ghouls and Hauntings Walking Tour](https://mediaim.expedia.com/localexpert/47668485/dd78fc5b-2837-423e-80a2-c4dfd8151a08.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### St. Louis Ghost Tour: Sinister Sins & Shadows

CA $44

per adult

[](https://expedia.ca/things-to-do/st-louis-ghost-tour-sinister-sins-shadows.a47668485.activity-details)

![St. Louis Small Group Walking Tour with St. Louis Arch and River Cruise](https://mediaim.expedia.com/localexpert/46042305/d8e03310-36fd-4d7b-8c16-28b00c937108.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### St. Louis Small Group Tour with St. Louis Arch & River Cruise

CA $196

per adult

[](https://expedia.ca/things-to-do/st-louis-small-group-tour-with-st-louis-arch-river-cruise.a46042305.activity-details)

[See all activities in Chesterfield](https://expedia.ca/things-to-do/search?rid=9530)

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