Holiday Rentals in Chesterfield

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Holiday Rentals in Chesterfield

Apartment in Grand Center

4.0 star property
8.6 out of 10, Excellent, (123)
"Very clean and very friendly people "
United States
Mary
The price is €135
includes taxes & fees
24 Nov - 25 Nov
White House at Grand Central

Holiday Home in St. Charles Historic District

10.0 out of 10, Exceptional, (135)
"We loved staying here in this adorable clean house that was only 1 block off of downtown Main Street shopping. "
United States
Lisa S.
The St. Charles Guest House, lovely historic home, fun for families and groups

Holiday Home in St. Charles Historic District

10.0 out of 10, Exceptional, (93)
"Check-in was easy and the house was lovely "
United States
Delfino A.
The price is €260
includes taxes & fees
3 Dec - 4 Dec
Stunning 1890's Home - Sleeps 8!

Cottage in St. Charles Historic District

10.0 out of 10, Exceptional, (210)
"Nice view of the Mississippi in the morning. Just off of the main street in old town St Charles, this place was perfect for our needs."
United States
Ralph
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!

Holiday Home in The Hill

9.8 out of 10, Exceptional, (156)
"Clean, very nice host, cute little building. It was a little warm in there with the window unit but other wise it was amazing "
United States
Lindsay
The price is €129
includes taxes & fees
30 Nov - 1 Dec
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!

Aparthotel in Maryland Heights

3.0 star property
7.0 out of 10, Good, (1110)
"We’ve stayed here twice before and have always been pleased with everything. Very good hotel close to what we need."
United States
Timothy
The price is €456
includes taxes & fees
24 Nov - 25 Nov
Value Suites Extended Stay - St Louis

Holiday Home in Saint Charles

9.8 out of 10, Exceptional, (25)
"The place was great! "
United States
Melissa I.
Home Near Main Street-Covered Patio-Hot Tub!

Apartment in St. Charles Historic District

9.6 out of 10, Exceptional, (12)
"Awesome place to stay"
United States
paul
Cozy Clark Suite in Frenchtown Saint Charles

Holiday Home in St. Charles Historic District

9.8 out of 10, Exceptional, (131)
"This was such a cute historical home and was perfect for our weekend in St Charles!"
United States
Isabelle C.
The price is €221
includes taxes & fees
24 Nov - 25 Nov
St. Charles 1860's Gem - Sleeps 6!

Aparthotel in St. Charles Historic District

9.4 out of 10, Exceptional, (12)
"We really enjoyed our stay! The Hare was an amazing suite & the location was great!"
United States
Angela R.
The Hare Suite at Divine Otter

Apartment in Hyde Park

6.4 out of 10, (13)
"We were pleased with our stay and would stay again"
United States
Nicole L.
Stylish City Reno Retreat!

Holiday Home in St. Charles Historic District

9.2 out of 10, Wonderful, (10)
"Great location close to historic district."
United States
Hugh S.
The price is €319
includes taxes & fees
27 Nov - 28 Nov
Honky Tonk Hideaway

Holiday Home in Tower Grove East

9.8 out of 10, Exceptional, (132)
"Our stay was exactly what we needed and that was a quick getaway. Thank you for your hospitality!"
United States
Johnathon F.
The price is €150
includes taxes & fees
30 Nov - 1 Dec
Centrally located in the Tower Grove East neighborhood!

Holiday Home in Northampton

2.0 star property
8.4 out of 10, Very good, (24)
"Excellent location very clean place "
United States
kimberly b.
The price is €280
includes taxes & fees
24 Nov - 25 Nov
Charming 3-bedroom house with WiFi, AC in the heart of St. Louis

Cabin in Marthasville

9.6 out of 10, Exceptional, (376)
"Very beautiful place to stay. We really enjoyed the lake. "
United States
Kristi W.
Authentic Log cabin with something for everyone!

Holiday Home in St. Charles Historic District

8.6 out of 10, Excellent, (14)
"The house was clean and well stocked, location was great, and plenty of street parking. "
United States
Brad K.
The price is €216
includes taxes & fees
1 Dec - 2 Dec
Madison House 1 -Walk to Main St

Apartment in Benton Park

9.2 out of 10, Wonderful, (17)
"This place is beautiful! Comfortable bed, big kitchen. Nice living room area. Quiet and safe. We liked it a lot. "
United States
Byard
Large Executive 1st Floor Apartment with Chefs Kitchen!

Holiday Home in St. Charles Historic District

9.2 out of 10, Wonderful, (11)
"The place wonderful and comfortable! Location was great and convenient. We would use this place again!"
United States
Anthony A.
The price is €213
includes taxes & fees
24 Nov - 25 Nov
5th Street #1 · Historic 5th Street House - Fully Rehabbed # 1

Holiday Home in St. Charles Historic District

9.0 out of 10, Wonderful, (19)
"Excellent location and a great space for 4 couples. The beds were exceptionally comfortable! "
United States
Kimberly C.
The price is €333
includes taxes & fees
24 Nov - 25 Nov
The Lewis & Clark Hangout

Apartment in St. Charles Historic District

9.8 out of 10, Exceptional, (99)
"The loft was very nice, very clean, well appointed, and in a perfect location. I highly recommend this property!"
United States
Mary ann S.
The price is €232
includes taxes & fees
24 Nov - 25 Nov
Prime Loft of Main Street
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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Top Chesterfield Hotel Reviews

Find out more about Chesterfield

Everything you need to know about Chesterfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterfield holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesterfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterfield holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesterfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterfield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Chesterfield?

Yes, there are holiday rentals in Chesterfield close to Chesterfield Sports Fusion, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Chesterfield. Make sure you have time to check out the sporting events and museums during your trip.

What are some of the best holiday rentals that Chesterfield has to offer?

Stunning 1890's Home - Sleeps 8! : This holiday home rental outside of Chesterfield is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Chesterfield?

Choose from 4 Expedia holiday rentals in Chesterfield for a memorable holiday.

What can I see and do in Chesterfield?

Family-friendly attractions include Chesterfield Sports Fusion and Sky Zone Indoor Trampoline Park - St. Louis, whereas Missouri River and Sophia M. Sachs Butterfly House are a couple of great spots to enjoy the outdoors. Other places in town to visit include The Factory and St. Louis Premium Outlets.

What are holiday rentals like in Chesterfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesterfield. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a family getaway.