Chesterfield holiday rentals

We found 1,759 holiday rentals — enter your dates for availability
Discover a selection of 8 homes and other holiday rentals in Chesterfield that are perfect for your trip. Holiday homes offer the amenities that you expect for your family, friends or furry companion, such as parking and a TV. At the end of the day, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Chesterfield

Showing deals for:25 Dec - 1 Jan

Property grounds
Exterior
Living area
Living area
Exceptional
(28 reviews)

Peaceful and cozy equestrian saturated retreat

Pacific

9% off
AU$1,328
for 7 nights, 1 cabin
AU$190 per night
includes taxes & fees
Peaceful and cozy equestrian saturated retreat
Dining area with fireplace and flat screen TV.
Master bedroom, king bed, flat screen TV, and fireplace.
Front door entrance.
Living room area with cozy seating and flat screen TV.
Exceptional
(146 reviews)

Adorable Two-Person Bungalow nestled in the cozy town of Augusta, MO!

Augusta

13% off
AU$1,707
for 7 nights, 1 cottage
AU$244 per night
includes taxes & fees
Adorable Two-Person Bungalow nestled in the cozy town of Augusta, MO!
Exterior detail
Living area
Private kitchen
Property grounds
Exceptional
(10 reviews)

Magnolia STL-Stylish 3BR Home w/ Garage by Hospitals,Universities, Zoo & Gardens

St. Louis

8% off
AU$4,892
for 7 nights, 1 home
AU$699 per night
includes taxes & fees
Magnolia STL-Stylish 3BR Home w/ Garage by Hospitals,Universities, Zoo & Gardens
Front living room
basketball court, and side view of property
Dining room
backyard at night
Wonderful
(32 reviews)

Elegant house pool, sports, pizza & boat bar, business center, mini theater.

St. Louis

8% off
AU$4,681
for 7 nights, 1 home
AU$669 per night
includes taxes & fees
Elegant house pool, sports, pizza & boat bar, business center, mini theater.
Dining
Living room with a sofa
Master bedroom with luxurious king bed, dresser, and attached bathroom & closet
Living room with a sofa
Exceptional
(17 reviews)

Perfect Getaway @ CWE- Entire Home + Free Parking Near Fox, Universities & More!

St. Louis

8% off
AU$5,303
for 7 nights, 1 home
AU$758 per night
includes taxes & fees
Perfect Getaway @ CWE- Entire Home + Free Parking Near Fox, Universities & More!
Living area
Private kitchen
Living area
Dining
Exceptional
(13 reviews)

Modern 4BR Retreat Near Fox & Universities @ Prime CWE Location w/ Free Parking!

St. Louis

8% off
AU$5,649
for 7 nights, 1 home
AU$807 per night
includes taxes & fees
Modern 4BR Retreat Near Fox & Universities @ Prime CWE Location w/ Free Parking!
Outdoor dining
Private kitchen
Room
Dining
Exceptional
(42 reviews)

O'Fallon Edge Oasis- 4bd/3bt, Wooded Backyard, Office, Great Family Getaway

O'Fallon

8% off
AU$3,811
for 7 nights, 1 home
AU$544 per night
includes taxes & fees
O'Fallon Edge Oasis- 4bd/3bt, Wooded Backyard, Office, Great Family Getaway
Exterior
Room
Living area
Living area
Exceptional
(9 reviews)

Old Town Charm | Historic St. Charles Retreat

St. Charles

8% off
AU$2,599
for 7 nights, 1 home
AU$371 per night
includes taxes & fees
Old Town Charm | Historic St. Charles Retreat
Living area
Property grounds
Pool
Room
Very good
(10 reviews)

Unique Home w/Private Pool, Fenced Yard, Projector & 1920's Style Speakeasy!

St. Louis

8% off
AU$4,614
for 7 nights, 1 home
AU$659 per night
includes taxes & fees
Unique Home w/Private Pool, Fenced Yard, Projector & 1920's Style Speakeasy!
Living area
Private kitchen
Outdoor dining
Dining
Exceptional
(61 reviews)

Modern Luxury 3-Story Brand New Home in STL

St. Louis

12% off
AU$5,313
for 7 nights, 1 home
AU$759 per night
includes taxes & fees
Modern Luxury 3-Story Brand New Home in STL
Room
Lovely equipped kitchen
Outdoor seating area, to eat and enjoy some fresh air!
Enclosed Patio with smart TV and games.
Wonderful
(9 reviews)

Luxurious & Peaceful 2BR/2BA!

St. Louis

11% off
AU$2,133
for 7 nights, 1 home
AU$305 per night
includes taxes & fees
Luxurious & Peaceful 2BR/2BA!
Famous statue next door
Eat in Kitchen for 6 with granite counters and stainless appliances
Eat in Kitchen for 6 with granite counters and stainless appliances
Large living room - washer and dryer - Space for 2 twin roll away beds for additional sleeping
Exceptional
(6 reviews)

Historic Craftsman • Hot Tub • Walk to Wineries • Katy Trail

Augusta

8% off
AU$3,547
for 7 nights, 1 home
AU$507 per night
includes taxes & fees
Historic Craftsman • Hot Tub • Walk to Wineries • Katy Trail
Interior
Dining
Private kitchen
Room
Wonderful
(5 reviews)

3Bed/2Bath perfect for families, couples or groups!

St. Louis

8% off
AU$2,454
for 7 nights, 1 home
AU$351 per night
includes taxes & fees
3Bed/2Bath perfect for families, couples or groups!
Room
Interior
Private kitchen
Living area
Exceptional
(13 reviews)

Charming, Pet friendly, Long stay discounts, 6 miles to Convention Center

St. Peters

8% off
AU$2,881
for 7 nights, 1 home
AU$412 per night
includes taxes & fees
Charming, Pet friendly, Long stay discounts, 6 miles to Convention Center
Living area
Living area
Outdoor dining
Interior
Exceptional
(80 reviews)

Urban Cottage Loft near Soulard Free Parking Pet Friendly

St. Louis

8% off
AU$1,003
for 7 nights, 1 apartment
AU$143 per night
includes taxes & fees
Urban Cottage Loft near Soulard Free Parking Pet Friendly
Exterior detail
Private kitchen
Dining
Room
Wonderful
(38 reviews)

Hidden Gem in the ❤ of STL

St. Louis

8% off
AU$1,541
for 7 nights, 1 home
AU$220 per night
includes taxes & fees
Hidden Gem in the ❤ of STL
kitchen
Exterior
Living Room
Property grounds
Exceptional
(15 reviews)

Rand House - near riverfront, wineries & Purina Farms

Washington

8% off
AU$2,919
for 7 nights, 1 home
AU$417 per night
includes taxes & fees
Rand House - near riverfront, wineries & Purina Farms
living room
lighted sidewalk to front door
washer/dryer closet
full kitchen
Exceptional
(12 reviews)

Charming 3-bedroom country house barndominium with WiFi in Union, pet friendly

Union

8% off
AU$1,860
for 7 nights, 1 home
AU$266 per night
includes taxes & fees
Charming 3-bedroom country house barndominium with WiFi in Union, pet friendly
Property grounds
Exterior
6S8A0168
6S8A0192
Exceptional
(48 reviews)

The Loft on Main | Steps to Dining & Nightlife

St. Charles

5% off
AU$3,043
for 7 nights, 1 room
AU$435 per night
includes taxes & fees
The Loft on Main | Steps to Dining & Nightlife
Property grounds
Private kitchen
Living area
Room
Exceptional
(18 reviews)

The Blue House near Frank Holten State Park / Golf /Lighthouse Restaurant

East St. Louis

16% off
AU$1,521
for 7 nights, 1 home
AU$217 per night
includes taxes & fees
The Blue House near Frank Holten State Park / Golf /Lighthouse Restaurant
Third Floor bedroom with one queen size bed and one full size bed.
Living area
Private kitchen
Balcony with seating.
Exceptional
(31 reviews)

Centrally Located Home Perfect for Family Getaway

St. Louis

20% off
AU$2,583
for 7 nights, 1 home
AU$369 per night
includes taxes & fees
Centrally Located Home Perfect for Family Getaway
Living area
Bedroom # 1 Queen size bed with smart tv
Kitchen
Interior
Wonderful
(32 reviews)

The Holly House. Comfort and Stylish charm.

Belleville

8% off
AU$1,867
for 7 nights, 1 home
AU$267 per night
includes taxes & fees
The Holly House. Comfort and Stylish charm.
Property grounds
Room
Exterior detail
Interior
Exceptional
(32 reviews)

Modern Boutique Stay w/ Plush King Bed- Hare Suite

St. Charles

7% off
AU$1,608
for 7 nights, 1 room
AU$230 per night
includes taxes & fees
Modern Boutique Stay w/ Plush King Bed- Hare Suite
Living area
Living area
Room
Private kitchen
Exceptional
(51 reviews)

Remodeled 3br 4ba Home with Secret Speakeasy Basement

St. Louis

12% off
AU$3,701
for 7 nights, 1 home
AU$529 per night
includes taxes & fees
Remodeled 3br 4ba Home with Secret Speakeasy Basement

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    More space, more privacy, more amenities — more value

The friendly city of Chesterfield awaits you

Enjoy the museums and other features of Chesterfield. This city's shopping, restaurants and sporting events attract many visitors, as does its welcoming and scenic location. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Chesterfield

Do you want to discover attractions to see in the area? Venture out of your holiday home and experience everything that makes Chesterfield a one-of-a-kind holiday spot. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • St. Louis Zoo (14.9 mi / 24 km)
  • Hidden Valley Ski Resort (9.9 mi / 15.9 km)
  • Six Flags St. Louis (11.7 mi / 18.9 km)
  • Chandler Hill Vineyards (12.9 mi / 20.8 km)
  • Sugar Creek Winery (13.2 mi / 21.2 km)
  • Grant's Farm (13.7 mi / 22.1 km)

Exploring the natural features in Chesterfield

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Chesterfield is a great place to spend some time outside. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Lou Fusz Soccer Complex (4.4 mi / 7.2 km)
  • Kirkwood Park (9.5 mi / 15.3 km)
  • West Tyson County Park (9.6 mi / 15.4 km)
  • Katy Trail (10.3 mi / 16.6 km)
  • August A. Busch Memorial Conservation Area (11.1 mi / 17.8 km)
  • Laumeier Sculpture Park (11.3 mi / 18.1 km)

Transport options to and around Chesterfield

The nearest airport is in St. Louis, MO (SUS-Spirit of St. Louis), located 4.4 mi (7 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Lambert-St. Louis International Airport (STL), which is 12.1 mi (19.4 km) away.

Frequently asked questions

What is the best area to stay in Chesterfield when booking a holiday rental?
When considering a holiday rental in Chesterfield, Missouri, a popular area to stay is near the vibrant Town and Country neighbourhood. This area boasts a delightful mix of upscale shopping and dining options, making it superb for those who enjoy a bit of retail therapy. You can explore the nearby Chesterfield Mall, which features a variety of stores and eateries, offering something for everyone.Another excellent choice would be the Chesterfield Valley area, known for its scenic landscapes and recreational opportunities. Here, you can enjoy the picturesque trails at the Chesterfield Valley Athletic Complex or visit the expansive Central Park, which hosts various events throughout the year and offers lovely picnic spots.In terms of holiday rentals, Chesterfield has a diverse range of properties, from charming townhouses to spacious family homes, suiting different preferences and group sizes. Each neighbourhood provides a special environment, allowing visitors to experience the local culture while enjoying convenient access to attractions and amenities.
What is the most popular type of holiday rental accomodation in Chesterfield?
In Chesterfield, apartments are the most popular type of holiday rental, with about 56 available throughout the area. These apartments are typically located in convenient neighbourhoods, providing easy access to local amenities and attractions. Most units come equipped with fully fitted kitchens, comfortable living areas, and often feature balconies or patios for relaxing outdoors. For those seeking more space, there are approximately 12 holiday houses available, which usually include multiple bedrooms, larger living areas, and private outdoor spaces, making them ideal for families or groups.
Are there any family house rentals in Chesterfield?
In Chesterfield, Missouri, there are several family house rentals available, making it an excellent choice for those travelling with children. The area boasts spacious homes in neighbourhoods like Longview Farm Park, where families can enjoy amenities such as large backyards, fully equipped kitchens for preparing family meals, and comfortable living spaces ideal for relaxation after a day of exploring.Visitors will appreciate the proximity to local attractions, including the popular Chesterfield Mall for shopping and dining, as well as the scenic trails and playgrounds at nearby parks. Additionally, families can take advantage of nearby recreational facilities offering sports fields and picnic areas, ensuring ample opportunities for outdoor fun.
Are there pet-friendly house rentals in Chesterfield?
In Chesterfield, there are several pet-friendly house rentals available, making it a suitable destination for travellers with furry companions. Many of these properties feature spacious layouts, fully equipped kitchens, and outdoor areas such as patios or gardens where pets can enjoy the fresh air. The neighbourhood offers a suburban atmosphere with easy access to local parks and green spaces, providing ample opportunities for pet walks and playtime. Additionally, the area is known for its family-friendly amenities, including nearby shops and restaurants that may also welcome pets.
Are there any remote work holiday rentals in Chesterfield?
In Chesterfield, Missouri, there are numerous holiday rentals suitable for remote work, with around 56 options available. Many of these properties provide essential amenities for a productive stay, including dedicated workspaces, high-speed Wi-Fi, and reliable internet access.Travellers can expect a variety of accommodations, from modern apartments to spacious homes, often featuring comfortable living areas and well-equipped kitchens. The proximity to local parks and recreational areas offers opportunities for breaks and relaxation, making it an ideal base for those blending work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Chesterfield?
In Chesterfield, popular rental amenities include well-equipped kitchens, allowing guests the convenience of preparing their own meals. Many rentals also feature dining areas for enjoying meals together, as well as comfortable desks ideal for those needing to work or study during their stay. Many properties offer balconies, providing a lovely spot to relax and take in the surrounding views. Additionally, fitness facilities are available in several rentals, suiting guests who wish to maintain their exercise routines while away.
When is the best time to visit Chesterfield for a holiday rental?
The peak season for visiting Chesterfield, Missouri, runs from May to July, with July being the most popular month for holiday rentals. During this time, visitors flock to the area to enjoy the vibrant outdoor activities and events, making it an ideal choice for those seeking a lively option. The warm weather, with temperatures averaging between 20 to 30 degrees Celsius, creates great conditions for exploring local parks, hiking trails, and nearby attractions.If you're keen on enjoying Chesterfield's outdoor offerings, including its beautiful parks and shopping districts, visiting in June can provide a great balance of pleasant weather and a bustling community vibe. However, for those looking for a quieter experience, November presents a wonderful opportunity. This low season offers a peaceful retreat, allowing you to explore the scenic beauty of Chesterfield without the crowds. Plus, the cooler temperatures in November can be quite refreshing, making it a wonderful time for leisurely walks and enjoying the autumn colours.Ultimately, the best time to book a holiday rental in Chesterfield will depend on your personal preferences for activity levels and comfort.
What are the top attractions in Chesterfield?
In Chesterfield, visitors can enjoy a variety of attractions that highlight the area's natural beauty and family-friendly activities. The Chesterfield Mall offers a wide range of shopping options, dining establishments, and entertainment, making it a popular destination for both locals and tourists. Nearby, the Chesterfield Valley Athletic Complex provides ample opportunities for sports enthusiasts, featuring fields for soccer, baseball, and other recreational activities.For those who appreciate the outdoors, the scenic Butterfly House is a must-visit, showcasing a diverse array of butterflies and offering educational experiences about these beautiful creatures. The area is also home to several parks, such as Faust Park, which boasts walking trails, picnic areas, and a historic carousel, allowing families to enjoy a day of relaxation and fun.In addition, the nearby Longview Farm Park offers picturesque landscapes and walking paths, great for leisurely strolls or family outings.
Are all fees included in the Chesterfield holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Chesterfield holiday homes with parking?
Stayz offers a wide selection of holiday homes in Chesterfield with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Chesterfield holiday homes?
You can find great discounts on holiday homes in Chesterfield on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Chesterfield holiday home booking on Stayz?
To find Chesterfield holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Chesterfield?
A long-stay holiday home in Chesterfield is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Chesterfield holiday home?
Book your Chesterfield holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chesterfield?
Prices for holiday homes in Chesterfield vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Chesterfield to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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