Chesterfield Holidays

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Things to do in and around Chesterfield

Chesterfield offers a delightful blend of family-friendly and entertainment-themed activities, making it an ideal holiday destination. Visitors can enjoy thrilling experiences at the local theatre, embark on an arcade adventure, or attend lively music concerts. With a variety of amusement experiences and engaging area activities, there's something for everyone to enjoy in this charming city.

Shopping

For a delightful shopping experience in Chesterfield, visit Kirkwood Farmer's Market, offering a charming atmosphere with local produce and crafts, just 16.1km away. If you're up for a drive, Mid Rivers Mall boasts a vibrant mix of shops and entertainment, located 16.1km from Chesterfield.

Recreation

Experience live music at The Factory, where the lively atmosphere sets the stage for memorable performances. For a dose of sports, head to Lou Fusz Soccer Complex, perfect for an active day. Alternatively, unwind at Bellerive Country Club, enjoying its luxurious ambience and beautiful surroundings.

Adventure

Experience the thrill of skiing at Hidden Valley Ski Resort, located 16.1km from Chesterfield, perfect for sports enthusiasts. For a scenic adventure, hike along the Katy Trail, also 16.1km away, where stunning outdoor views await. Alternatively, join activities at The J - Chesterfield Gym & Fitness Center in town.

Nightlife

In Chesterfield, the vibrant Chesterfield Sports Fusion offers an exhilarating arcade adventure atmosphere, perfect for family fun. Nearby, the St. Louis Carousel provides a whimsical amusement ride experience. For a touch of romance and culture, the New Jewish Theatre, located 14.5km away, presents captivating performances.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Chesterfield

Chesterfield offers a delightful blend of family-friendly and entertainment-focused attractions, making it an ideal destination for a city-themed holiday. Visitors can explore modern colleges and universities, enjoy events at local entertainment arenas, and unwind in picturesque urban parks. With a variety of cultural experiences and outdoor activities, Chesterfield caters to those seeking both leisurely family outings and engaging adventures in a vibrant community.

  • Hollywood Casino Amphitheatre: Experience live entertainment in a vibrant atmosphere at this renowned amphitheatre, located 12.9km from Chesterfield. Enjoy concerts under the stars, with a lively family-friendly vibe that makes for an unforgettable evening out.
  • Westport Plaza: Immerse yourself in the bustling city vibes of Westport Plaza, situated 11.3km from Chesterfield. This vibrant neighbourhood boasts an array of dining, shopping, and entertainment options, perfect for a leisurely day exploring local culture.
  • Washington University in St. Louis: Discover the stunning campus of this prestigious university, located 22.5km away. With its impressive architecture and beautifully landscaped grounds, it offers a serene environment ideal for a peaceful stroll while soaking in academic excellence.

Best time to go to Chesterfield

The best time to visit Chesterfield is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.6°F (-0.2°C)Light RainMostly CloudyAverageSlightly Low
February34.7°F (1.5°C)Light RainMostly SunnyAverageSlightly Low
March46.4°F (8.0°C)Light RainMostly SunnyAverageAverage
April55.9°F (13.3°C)Light RainMostly SunnySlightly HighAverage
May66.2°F (19.0°C)Light RainMostly SunnyAverageSlightly High
June75.9°F (24.4°C)Light RainMostly SunnySlightly HighSlightly High
July79.0°F (26.1°C)Light RainMostly SunnySlightly HighSlightly High
August77.2°F (25.1°C)Light RainMostly SunnyAverageAverage
September70.9°F (21.6°C)Light RainMostly SunnyAverageAverage
October58.5°F (14.7°C)Light RainMostly SunnySlightly LowAverage
November46.2°F (7.9°C)Light RainMostly SunnySlightly LowAverage
December37.6°F (3.1°C)Light RainMostly SunnySlightly LowSlightly Low

Booking tips and Expedia advantages for Chesterfield

Chesterfield offers numerous free attractions, including Westport Plaza and Historic Main Street. To save on travel costs, consider visiting between December and February, when accommodation prices are lower, particularly on Mondays. For transport, utilise a bicycle or walk, as Chesterfield is pedestrian-friendly. Use Expedia to find eco-certified hotels and combine your bookings for additional savings. Remember to filter results by price to secure the best deals, ensuring an enjoyable yet budget-friendly stay in Chesterfield.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Chesterfield are December to February, where the prices are slightly lower. This is in comparison to May to July, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Chesterfield is Monday. The most expensive day to stay in Chesterfield is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia's search tool to refine your preferences, such as your budget, desired location, and preferred type of accommodation. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels currently available. To find the best prices and offers, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel reservation in Chesterfield with your flights and activities through an Expedia package.

Top hotels in Chesterfield

Hyatt Place St. Louis/Chesterfield

Hyatt Place St. Louis/Chesterfield

3 out of 5
333 Chesterfield Center East, Chesterfield, MO
Fully refundableReserve now, pay when you stay
The price is Rp2.045.613 per night from 23 Nov to 24 Nov
Rp2.045.613
Rp2.372.666 total
23 Nov - 24 Nov
includes taxes & fees
9.4/10 Exceptional! (1,022 reviews)
Clean room and overall hotel, good breakfast, convenient location

Reviewed on 30 Oct 2025

Hyatt Place St. Louis/Chesterfield
Sonesta ES Suites St. Louis - Chesterfield

Sonesta ES Suites St. Louis - Chesterfield

3 out of 5
15431 Conway Rd, Chesterfield, MO
Fully refundableReserve now, pay when you stay
The price is Rp1.543.357 per night from 12 Nov to 13 Nov
Rp1.543.357
Rp1.790.109 total
12 Nov - 13 Nov
includes taxes & fees
7.8/10 Good! (1,009 reviews)
Everything was excellent. The only issue we had was finding a parking space.

Reviewed on 24 Oct 2025

Sonesta ES Suites St. Louis - Chesterfield
Drury Plaza Hotel St. Louis Chesterfield

Drury Plaza Hotel St. Louis Chesterfield

3 out of 5
355 Chesterfield Ctr, Chesterfield, MO
Fully refundableReserve now, pay when you stay
The price is Rp2.161.864 per night from 9 Nov to 10 Nov
Rp2.161.864
Rp2.507.456 total
9 Nov - 10 Nov
includes taxes & fees
9.6/10 Exceptional! (1,015 reviews)
Staff very courteous, breakfast was very good-room is OK

Reviewed on 28 Oct 2025

Drury Plaza Hotel St. Louis Chesterfield
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.

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What to do in Chesterfield

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