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Chesterfield Holiday Rentals

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Holiday Rentals in Chesterfield

Comfort Apartment
White House at Grand Central
3.0 star property
9.0 out of 10, Wonderful, (69)
"Second time I’ve stayed and it was even better than the first! Had some bottles of wine and glasses out set out when I arrived! It’s the little things that matter! "
The price is NZ$336
includes taxes & fees
22 May - 23 May
White House at Grand Central
Reception
Kasa Forest Park St. Louis
3.5 star property
9.0 out of 10, Wonderful, (98)
"The apartment was amazing! The outdoor patio near the club house was messy and i was nervous to use the hot tub. I was disappointed because i really wanted a use the outdoors space. But otherwise it was great! "
Kasa Forest Park St. Louis
Bar (on property)
The St. Charles Guest House, lovely historic home, fun for families and groups
10.0 out of 10, Exceptional, (106)
"Had a wonderful weekend get away in St. Charlies. The house was so close to main street, but far enough away not to hear the noise. The house had everything and more! The water and snacks were a nice touch. Everything was very clean. Would stay here again."
The St. Charles Guest House, lovely historic home, fun for families and groups
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Desk, laptop workspace, blackout curtains, WiFi
Craigshire Suites
3.0 star property
7.0 out of 10, Good, (1105)
"Great customer service "
The price is NZ$519
includes taxes & fees
3 Jun - 4 Jun
Craigshire Suites
Bar (on property)
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!
10.0 out of 10, Exceptional, (184)
"The cottage is immaculately furnished inside, and the bed is very comfortable. Just a very short walk to Main Street. Would recommend to anyone who is visiting St. Charles."
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!
Living area
Funky mini loft in fox park! Pet friendly!!
7.0 out of 10, Good, (12)
"The Nicolas Cage decor was great! We loved the effort that went into it. It was decently clean; however, it was very cold in the property. When we went to sleep it was 60 degrees in there and we had no way to change it."
The price is NZ$240
includes taxes & fees
23 May - 24 May
Funky mini loft in fox park! Pet friendly!!
Fridge, microwave, oven, stovetop
Stunning Townhome in The Grove - 918
9.6 out of 10, Exceptional, (21)
"This location has the WOW factor!! Such a peaceful area filled with inspiration and love ❤️. My family and I enjoyed this home away from home ❤️ The host was so accommodating and communication was everything! Highly recommend 👌"
The price is NZ$488
includes taxes & fees
28 May - 29 May
Stunning Townhome in The Grove - 918
Reception
Kasa Central West End St. Louis
3.5 star property
8.6 out of 10, Excellent, (34)
"Loved everything about this property. Would suggest additional tv and additional comfortable seating in living room. Thank you for a safe and enjoyable stay."
Kasa Central West End St. Louis
Fridge, microwave, oven, stovetop
Cozy Soulard 2BR w/ Free Parking
10.0 out of 10, Exceptional, (15)
"Wonderful location with wonderful hosts-super easy to communicate with. Highly recommended!!"
The price is NZ$319
includes taxes & fees
19 May - 20 May
Cozy Soulard 2BR w/ Free Parking
Fridge, microwave, oven, stovetop
Beautiful, Brand New Tower Grove Unit! 1s
9.8 out of 10, Exceptional, (6)
"Awesome Host. Always enjoy my stay."
The price is NZ$359
includes taxes & fees
22 May - 23 May
Beautiful, Brand New Tower Grove Unit! 1s
Fridge, microwave, oven, stovetop
Classic FoxPark King 3BR w/ Deck
10.0 out of 10, Exceptional, (18)
"My family had such a nice stay. We were in town for a concert, and our stay was so fitting for everything we did. We loved the area, the house’s character, and all the handy accommodations. We all slept comfortably in our own spaces. If/when I return to the area, I won’t look for another place to stay; I’ll just easily book this again!"
The price is NZ$302
includes taxes & fees
22 May - 23 May
Classic FoxPark King 3BR w/ Deck
Fridge, microwave, oven, stovetop
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
9.8 out of 10, Exceptional, (97)
"Host met us when we arrived. He was very nice. Took the time to show us everything and answer our questions. First VRBO. It was a pleasant experience. Our host John stocked our kitchen with drinks, fresh fruit and coffee pods. Plenty of corner dining spots near by. We would stay again!! Thanks John and Mary for a good stay!"
The price is NZ$238
includes taxes & fees
15 May - 16 May
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
Pool
☆BackYard BBQ Hidden Gem☆Perfect Location~Groups /Pets Welcome
9.0 out of 10, Wonderful, (40)
"Dirty, animal hair everywhere, stunk of animals, mouse traps everywhere, mouse poop all over, clothes in the dryer, shower faucet was half broken, bed sheets and animals hair, not a 4 bedroom as advertised, air mattresses all had holes. Not at all acceptable for a "vacation rental", 2 nights we stayed and it was not cheap, I expected way more."
☆BackYard BBQ Hidden Gem☆Perfect Location~Groups /Pets Welcome
Fridge, microwave, oven, stovetop
Spacious Shaw 2 Bedroom Walk to Botanical Garden & Tower Grove - Pet Friendly
9.8 out of 10, Exceptional, (41)
"This home is in a great location. Walkable to parks and restaurants. Neighbors are friendly. Would love to stay on future trips."
Spacious Shaw 2 Bedroom Walk to Botanical Garden & Tower Grove - Pet Friendly
Exterior
Authentic Log cabin with something for everyone!
9.6 out of 10, Exceptional, (313)
"Me and a couple of my besties stayed for the weekend so we could run a race, and enjoy some wineries near by. The cabin was so great! Very chill and relaxing. Lots of space, comfortable beds, and we felt very safe! We will definitely be renting again!"
Authentic Log cabin with something for everyone!
Exterior
Entire Dogtown House near Zoo, Forest Park and Wash U
10.0 out of 10, Exceptional, (166)
"Excllent property in a great location and close to everything in STL"
The price is NZ$336
includes taxes & fees
23 May - 24 May
Entire Dogtown House near Zoo, Forest Park and Wash U
Interior
Chic Loft wlk to CityMu, CnvnCtr & Aquarium pets welcome
8.0 out of 10, Very good, (8)
"This place was great and I would stay here any time I'm in the area. The host was beyond helpful and friendly. I would choose this over any hotel. Great location for families with children."
Chic Loft wlk to CityMu, CnvnCtr & Aquarium pets welcome
Property grounds
StL's ‘The Hill' NBHD. Famous for all things Italian. Cozy & clean 2nd fl apt.
10.0 out of 10, Exceptional, (219)
"Loved our stay."
The price is NZ$252
includes taxes & fees
13 May - 14 May
StL's ‘The Hill' NBHD. Famous for all things Italian. Cozy & clean 2nd fl apt.
Fridge, microwave, oven, stovetop
BRAND NEW! Newly Furnished, Swanky Home with Great Location!
10.0 out of 10, Exceptional, (24)
"The house was immaculate, neighborhood was peaceful, and in a perfect location with plenty of fun activities and great food options nearby."
BRAND NEW! Newly Furnished, Swanky Home with Great Location!
Exterior
1790's Renovated Barn, Main Street St. Charles, Hot Tub in private backyard!
10.0 out of 10, Exceptional, (185)
"We had a great time! The Red Barn was just what we needed for some quiet time to relax and take our time in St. Charles. The location is the perfect distance from the main street so you don't have to walk far to find something to do, but it's also not right on the "main drag" where you'd have people walking by all the time. Thanks for the hospitality!"
1790's Renovated Barn, Main Street St. Charles, Hot Tub in private backyard!
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See all available properties in 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.

Other types of properties in Chesterfield you may be interested in

Studio Suite, 1 King Bed
Sonesta ES Suites St. Louis - Chesterfield
3.0 star property
8.4 out of 10, Very good, (1001)
"Just what we needed. Having 2 bathrooms was amazing!"
The price is NZ$193
includes taxes & fees
29 May - 30 May
Sonesta ES Suites St. Louis - Chesterfield
Exterior
Drury Plaza Hotel St. Louis Chesterfield
3.0 star property
9.6 out of 10, Exceptional, (1004)
"The workers are kind and nice Their meals are good too. Good job."
The price is NZ$247
includes taxes & fees
19 May - 20 May
Drury Plaza Hotel St. Louis Chesterfield
Exterior
Hyatt Place St. Louis/Chesterfield
3.0 star property
9.4 out of 10, Exceptional, (1000)
"Friendly staff. Top floor quiet"
The price is NZ$258
includes taxes & fees
28 May - 29 May
Hyatt Place 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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chesterfield holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Chesterfield. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Chesterfield. Seeing all the best attractions is bound to make you fall in love with Chesterfield. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Chesterfield short-term rentals, that won’t be hard to do.

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.

How many holiday rentals are there in Chesterfield?

Choose from 17 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. While in the area, you can also visit popular places such as Six Flags St. Louis and St. Louis Zoo.

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.

Recent reviews of Chesterfield properties
Expedia verified reviews