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Holiday Rentals in Chesterfield

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Holiday Rentals in Chesterfield

White House at Grand Central
3.0 star property
9.0 out of 10, Wonderful, (71)
"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 €135
per night
5 Jun - 6 Jun
White House at Grand Central
Kasa Forest Park St. Louis
3.5 star property
9.0 out of 10, Wonderful, (99)
"Great property and a really cool vibe in this part of the city."
Kasa Forest Park St. Louis
The St. Charles Guest House, lovely historic home, fun for families and groups
10.0 out of 10, Exceptional, (107)
"This house was perfect for our family to hang out and hit Main Street in St. Charles. The house itself has an updated kitchen and bathrooms and has enough space for a big family chill and watch movies or play video games. It is within walking distance of all the attractions on Main Street and if you are up to it, the Ameristar casino."
The St. Charles Guest House, lovely historic home, fun for families and groups
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Kasa Central West End St. Louis
3.5 star property
8.6 out of 10, Excellent, (35)
"Highly recommend!"
Kasa Central West End St. Louis
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!
Stunning Townhome in The Grove - 918
9.4 out of 10, Exceptional, (24)
"The property was in a good location. Just one block away from nightlife and fun. "
The price is €256
per night
5 Jun - 6 Jun
Stunning Townhome in The Grove - 918
Funky mini loft in fox park! Pet friendly!!
7.2 out of 10, Good, (15)
"Nicholas Cage was definitely an unexpected surprise. But was a unique experience that I’m sure me and my friends will joke about for time to come. I did think the front yard look messy with the excessive amount of trees. And stair to the loft are steep and should be included in the listing. Those are just minor inconveniences out experience was over all a great one and I would choose this place again."
The price is €127
per night
12 Jun - 13 Jun
Funky mini loft in fox park! Pet friendly!!
Cozy Soulard 2BR w/ Free Parking
10.0 out of 10, Exceptional, (15)
"It was cozy, clean and comfortable. Loved it."
The price is €174
per night
18 Jun - 19 Jun
Cozy Soulard 2BR w/ Free Parking
Classic FoxPark King 3BR w/ Deck
10.0 out of 10, Exceptional, (22)
"This apartment was just what I needed for my stay. I loved the use of reclaimed wood in the space. It gave it an old feel, yet was very up-to-date. It was very clean and felt comfortable. I loved some of the interesting items used in the decor. I appreciated the host's dining suggestions that could be found nearby."
The price is €197
per night
17 Jun - 18 Jun
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, (221)
"We had a lovely evening/morning at this lovely apartment on The Hill. Close to restaurants, a park, and more. Clean and with everything we needed, including coffee. We would stay here again."
The price is €146
per night
1 Jul - 2 Jul
StL's ‘The Hill' NBHD. Famous for all things Italian. Cozy & clean 2nd fl apt.
☆BackYard BBQ Hidden Gem☆Perfect Location~Groups /Pets Welcome
9.0 out of 10, Wonderful, (41)
"My friends had a good time on our weekend stay. The neighborhood and neighbors were really nice. The outdoor area was a bonus, we liked the patio and yard space for outdoor activities. The house had everything we needed and were even provided extra toiletries. My only complaint would be the sleeping arrangements, the pull out bed wasn’t comfortable but we doubled up on mattresses and it worked out fine."
☆BackYard BBQ Hidden Gem☆Perfect Location~Groups /Pets Welcome
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
Authentic Log cabin with something for everyone!
9.6 out of 10, Exceptional, (316)
"We liked the cabin and my grandkids like feeding the fish and playing in the water.There where just 2 things that bothered me.The black ants where bad and the kitchen oven was really dirty.Other than that we enjoyed our stay very much."
Authentic Log cabin with something for everyone!
Spacious Shaw 2 Bedroom - Walk to Botanical Garden & Tower Grove - Pet Friendly
9.8 out of 10, Exceptional, (42)
"This property is nestled in a great neighborhood and within a short distance to Botanical Gardens and restaurants. Very quiet, too. Our only complaint - uncomfortable beds."
Spacious Shaw 2 Bedroom - Walk to Botanical Garden & Tower Grove - Pet Friendly
St Louis Townhome-Perfect for Groups!
8.6 out of 10, Excellent, (19)
"Checking in was a bit confusing as the address given was not the side I stayed in. It was smaller in person than on the pictures but overall the stay was nice, would book again."
The price is €228
per night
3 Jun - 4 Jun
St Louis Townhome-Perfect for Groups!
Entire Dogtown House near Zoo, Forest Park and Wash U
10.0 out of 10, Exceptional, (170)
"Nice place. Suited our needs for attending a graduation at WashU. Only issue was the information emailed to us mentioned a pull-out sofa, but the location does not have one. Also, the WiFi information in the book wasn’t accurate and the correct information was sent in the check-in email. Bare bones, but covered what we needed."
The price is €192
per night
2 Jul - 3 Jul
Entire Dogtown House near Zoo, Forest Park and Wash U
Cozy Cottage, we're told it's heavenly!
10.0 out of 10, Exceptional, (150)
"The host goes the extra mile in making sure that everything is provided for! We enjoyed the experience."
Cozy Cottage, we're told it's heavenly!
Beautiful, Brand New Tower Grove Unit! 1s
9.8 out of 10, Exceptional, (7)
"Clean, comfortable, roomy 3 bedroom. Quiet and safe neighborhood ."
The price is €210
per night
18 Jun - 19 Jun
Beautiful, Brand New Tower Grove Unit! 1s
Plush Living next to BJC/ZOO/FOREST PARK/WASHU
9.0 out of 10, Wonderful, (31)
"We had a solid experience at Arthur's place. His instructions for check-in and all other processes were very accurate and user-friendly. One suggestion we have is to fix the bathtub faucet."
The price is €156
per night
3 Jun - 4 Jun
Plush Living next to BJC/ZOO/FOREST PARK/WASHU
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
9.8 out of 10, Exceptional, (102)
"We loved that parking was easy and the neighborhood was very walkable. It may be too far away for some folks, but we were able to walk to the Botanic Garden and have a nice outing. Everything about the stay was easy and we appreciated that the hosts had things set up to meet our needs when we arrived."
The price is €146
per night
1 Jul - 2 Jul
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
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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.

Other types of properties in Chesterfield you may be interested in

Sonesta ES Suites St. Louis - Chesterfield
3.0 star property
8.2 out of 10, Very good, (1006)
"I love this place great for families and couples "
The price is €95
per night
18 Jun - 19 Jun
Sonesta ES Suites St. Louis - Chesterfield
Drury Plaza Hotel St. Louis Chesterfield
3.0 star property
9.6 out of 10, Exceptional, (1005)
"It was very friendly and fun"
The price is €160
per night
2 Jun - 3 Jun
Drury Plaza Hotel St. Louis Chesterfield
Hyatt Place St. Louis/Chesterfield
3.0 star property
9.4 out of 10, Exceptional, (1004)
"Great room, very spacious and service was good and responded quickly. Very clean"
The price is €149
per night
17 Jun - 18 Jun
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.

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 €127 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.

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.

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