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Chesterfield Holiday Rentals

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Holiday Rentals in Chesterfield

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
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!
Fridge, microwave, oven, stovetop
Cozy Soulard 2BR w/ Free Parking
10.0 out of 10, Exceptional, (15)
"It was cozy, clean and comfortable. Loved it."
The price is HK$547
HK$1,347 total
includes taxes & fees
20 May - 21 May
Cozy Soulard 2BR w/ Free Parking
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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 HK$547
HK$1,421 total
includes taxes & fees
20 May - 21 May
Classic FoxPark King 3BR w/ Deck
Exterior
Entire Dogtown House near Zoo, Forest Park and Wash U
10.0 out of 10, Exceptional, (167)
"Excllent property in a great location and close to everything in STL"
The price is HK$938
HK$1,594 total
includes taxes & fees
14 May - 15 May
Entire Dogtown House near Zoo, Forest Park and Wash U
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 HK$617
HK$1,191 total
includes taxes & fees
14 May - 15 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!
Exterior
Cozy Cottage, we're told it's heavenly!
10.0 out of 10, Exceptional, (147)
"This cabin and property setting is perfect for a quiet, romantic getaway! It has that secluded, country feeling, yet was close enough to the Washington riverfront and nearby wineries. The indoor jetted tub is a nice, large size. We enojoyed the deck and porch swing. We appreciated the drinks and snacks provided by the hosts. Would definitely visit again!"
Cozy Cottage, we're told it's heavenly!
Fridge, microwave, oven, stovetop
Central St Louis apartment 2E
10.0 out of 10, Exceptional, (2)
"We wanted an affordable, comfortable place to rest after exploring the city. This place offered that. Very happy."
The price is HK$508
HK$1,688 total
includes taxes & fees
28 May - 29 May
Central St Louis apartment 2E
Fridge, microwave, oven, stovetop
Beautiful, Brand New Tower Grove Unit! 1s
9.8 out of 10, Exceptional, (6)
"Comforting, Love the community, location beautiful apartment."
The price is HK$445
HK$1,735 total
includes taxes & fees
27 May - 28 May
Beautiful, Brand New Tower Grove Unit! 1s
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 HK$695
HK$1,150 total
includes taxes & fees
20 May - 21 May
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
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
1 bedroom, iron/ironing board, free WiFi, bed sheets
Soulard Pet Friendly 1 Bedroom with In-Unit Washer Dryer - Long Term Welcome
9.8 out of 10, Exceptional, (26)
"The place was clean enough, however the basement where the bedroom was, smelled like mold the entire time we were there. It gave me a headache. Also parking was difficult--we got a ticket because we didn't read the sign that was over 50 feet away stating they were cleaning the streets and not to park. I wouldn't stay here again."
Soulard Pet Friendly 1 Bedroom with In-Unit Washer Dryer - Long Term Welcome
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 HK$469
HK$1,875 total
includes taxes & fees
19 May - 20 May
Stunning Townhome in The Grove - 918
Exterior
Authentic Log cabin with something for everyone!
9.6 out of 10, Exceptional, (313)
"Rustic, spacious, good outdoor areas, peaceful private lake, well equipped. Nearby neighbors but not intrusive. Had weather cooperated better it would have been an ideal setting for our retreat."
Authentic Log cabin with something for everyone!
Dining
The Lofts of North Main Street
9.6 out of 10, Exceptional, (88)
"Very pleasant, clean space to stay. Very conveniently located. Easy host to work with."
The price is HK$930
HK$1,996 total
includes taxes & fees
14 May - 15 May
The Lofts of North Main Street
Interior
Rustic Charm 4BDRM Home| STL Developers
9.6 out of 10, Exceptional, (25)
"St. Louis received several inches of snow on our arrival day. The property manager called to let us know they had cleared and salted the front steps as well as the back sidewalk and porch. We really appreciated that extra touch of attention. The property has plenty of parking. We would recommend this property to anyone visiting St. Louis."
Rustic Charm 4BDRM Home| STL Developers
Interior
Jaw Dropping New York Experience 2 Bedroom
9.6 out of 10, Exceptional, (5)
"Great overall experience. Please install a safety bar in the front bathtub to help prevent falls."
Jaw Dropping New York Experience 2 Bedroom
Living area
A Touch of Key West
9.6 out of 10, Exceptional, (36)
"Beverly and Tim were great hosts! The place is super cute, clean, and comfy. Very close to dining options and touristic places. I went with my partner to ser the Eclipse, but we were also able to walk around Saint Louis and know more about the city. If we'll come back to St. Louis, we'll definitely be in touch with then again. Very happy to have stayed there :) "
A Touch of Key West
Don't see what you're looking for?
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

Exterior
Drury Plaza Hotel St. Louis Chesterfield
3.0 star property
9.6 out of 10, Exceptional, (1007)
"The workers are kind and nice Their meals are good too. Good job."
The price is HK$1,006
HK$1,166 total
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, (1002)
"Friendly staff. Top floor quiet"
The price is HK$1,050
HK$1,218 total
includes taxes & fees
28 May - 29 May
Hyatt Place St. Louis/Chesterfield
Exterior
DoubleTree by Hilton Hotel St. Louis - Chesterfield
4.0 star property
8.6 out of 10, Excellent, (1001)
"The staff was really nice and helpful. The hotel overall was really really nice but the cookies they give you are amazing!!"
The price is HK$1,064
HK$1,235 total
includes taxes & fees
19 May - 20 May
DoubleTree by Hilton 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.

Search for holiday rentals in Chesterfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesterfield using one of the methods below:

  • View our selection of featured holiday rentals in Chesterfield
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Look no further and take a look at our great range of rental properties in Chesterfield!

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

Best Western St. Louis-Kirkwood Route 66

Best Western St. Louis-Kirkwood Route 66

5/5 Excellent
"Always a great stay here!"
A verified traveller stayed at Best Western St. Louis-Kirkwood Route 66
Posted 20 hours ago
Best Western St. Louis-Kirkwood Route 66