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Search Holiday Rentals in Chesterfield

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Top Holiday Rentals in Chesterfield

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
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!
Cozy Soulard 2BR w/ Free Parking
10.0 out of 10, Exceptional, (14)
"Wonderful location with wonderful hosts-super easy to communicate with. Highly recommended!!"
The price is £141
per night
7 May - 8 May
Cozy Soulard 2BR w/ Free Parking
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Entire Dogtown House near Zoo, Forest Park and Wash U
10.0 out of 10, Exceptional, (165)
"We stayed here after a party at the zoo. It was in a great location, exactly what it looked like in the listing, it had a comfortable bed, and was a great experience."
The price is £165
per night
27 May - 28 May
Entire Dogtown House near Zoo, Forest Park and Wash U
BRAND NEW! Newly Furnished, Swanky Home with Great Location!
10.0 out of 10, Exceptional, (23)
"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!
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 £148
per night
9 May - 10 May
Classic FoxPark King 3BR w/ Deck
StL's ‘The Hill' NBHD. Famous for all things Italian. Cozy & clean 2nd fl apt.
10.0 out of 10, Exceptional, (218)
"Super cute and quaint and very close to several local spots in the Hill. A nice park across the street. Sofa and sofa bed not very comfy but the bed was nice. It’s the perfect space for a weekend stay! "
The price is £125
per night
9 May - 10 May
StL's ‘The Hill' NBHD. Famous for all things Italian. Cozy & clean 2nd fl apt.
Cozy Cottage, we're told it's heavenly!
10.0 out of 10, Exceptional, (147)
"Loved this cozy little peaceful property. Tucked into the hills woods perfectly with trails nearby. Short drive to Washington MO. I'll definitely be staying here again"
Cozy Cottage, we're told it's heavenly!
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 £172
per night
7 May - 8 May
Central St Louis apartment 2E
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!
Stylish FoxPark 3BR, King Master
10.0 out of 10, Exceptional, (18)
"Beautiful and well decorated apartment."
The price is £149
per night
7 May - 8 May
Stylish FoxPark 3BR, King Master
Cowboy cabin, March availability, look for discounted weekly rates!
10.0 out of 10, Exceptional, (163)
"My stay at the cabin was very peaceful and easy. I couldn't ask any more from the owners. My kid LOVED the loft space and the owners dogs that would visit from time to time"
Cowboy cabin, March availability, look for discounted weekly rates!
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 £117
per night
5 May - 6 May
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
Beautiful, Brand New Tower Grove Unit! 1s
9.6 out of 10, Exceptional, (5)
"Awesome Host. Always enjoy my stay."
The price is £181
per night
28 May - 29 May
Beautiful, Brand New Tower Grove Unit! 1s
Authentic Log cabin with something for everyone!
9.6 out of 10, Exceptional, (312)
"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!
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
Rustic Charm 4BDRM Home| STL Developers
9.6 out of 10, Exceptional, (24)
"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
South City Historic Home w/ private carport
9.6 out of 10, Exceptional, (27)
"We stayed in this beautiful historic 2-story home in St Louis, MO for a week. Very nicely decorated, furnished and had everything we needed for a comfortable stay. The carport with garage door was a bonus. Owner was quick to respond to any questions we had. The area was an older part of town they are refurbishing, but we felt safe and liked the historic structure. Would recommend if you are visiting St Louis or any of the surrounding areas."
The price is £306
per night
7 May - 8 May
South City Historic Home w/ private carport
Stunning Townhome in The Grove - 918
9.4 out of 10, Exceptional, (19)
"We had a wonderful stay, beds were super comfortable and blankets were amazing. The house was located in the perfect spot for where we wanted to be."
The price is £196
per night
5 May - 6 May
Stunning Townhome in The Grove - 918
♦️POSH LOFT♦️ Walk to CtyMu | Cvtn Ctr | Aquarium
9.4 out of 10, Exceptional, (19)
"Property is nice. Parking garage is horrible! Spaces are very tiny and people parked in our spot 2nd night. Arthur did quickly reimburse us for the amt we had to pay to park but it was annoying."
♦️POSH LOFT♦️ Walk to CtyMu | Cvtn Ctr | Aquarium
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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.

Chesterfield Holiday Rental Travel Info

Other types of properties in Chesterfield you may be interested in

Drury Plaza Hotel St. Louis Chesterfield
3.0 star property
9.6 out of 10, Exceptional, (1006)
"Staff is friendly, hotel is clean and quiet. "
The price is £115
per night
5 May - 6 May
Drury Plaza Hotel St. Louis Chesterfield
Hyatt Place St. Louis/Chesterfield
3.0 star property
9.6 out of 10, Exceptional, (1001)
"Clean quiet hotel. Very friendly helpful service "
The price is £138
per night
16 May - 17 May
Hyatt Place St. Louis/Chesterfield
DoubleTree by Hilton Hotel St. Louis - Chesterfield
4.0 star property
8.6 out of 10, Excellent, (1000)
"Very friendly staff"
The price is £105
per night
26 May - 27 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.

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 £117 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?

Funky mini loft in fox park! Pet friendly!!: This holiday home rental outside of Chesterfield has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals are there in Chesterfield?

Choose from 15 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.

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