Photo by Michelle E

Chesterfield Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Find properties with these dates

This weekend
Next weekend

Holiday Rentals in Chesterfield

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 AU$430
per night
3 May - 4 May
Craigshire Suites
Comfort Apartment
White House at Grand Central
3.0 star property
9.2 out of 10, Wonderful, (66)
"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 AU$226
per night
7 May - 8 May
White House at Grand Central
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
Save an average of 15% on thousands of hotels when you're signed in
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!!
7.4 out of 10, Good, (10)
"It is bigger on the inside. We loved our time here."
The price is AU$207
per night
9 May - 10 May
Funky mini loft in fox park! Pet friendly!!
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
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
Fridge, microwave, oven, stovetop
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 AU$372
per night
5 May - 6 May
Stunning Townhome in The Grove - 918
Fridge, microwave, oven, stovetop
Beautiful, Brand New Tower Grove Unit! 1s
9.6 out of 10, Exceptional, (5)
"Awesome Host. Always enjoy my stay."
The price is AU$336
per night
21 May - 22 May
Beautiful, Brand New Tower Grove Unit! 1s
Fridge, microwave, oven, stovetop
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 AU$267
per night
6 May - 7 May
Cozy Soulard 2BR w/ Free Parking
Exterior
♦️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
Exterior
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!
Reception
Kasa Central West End St. Louis
3.5 star property
8.6 out of 10, Excellent, (33)
"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
Exterior
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 AU$311
per night
14 May - 15 May
Entire Dogtown House near Zoo, Forest Park and Wash U
Fridge, microwave, oven, stovetop
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!
Fridge, microwave, oven, stovetop
Tower Grove South 1BR Gingerbread House
9.0 out of 10, Wonderful, (14)
"Comfortable home for the weekend."
Tower Grove South 1BR Gingerbread House
Pool
☆BackYard BBQ Hidden Gem☆Perfect Location~Groups /Pets Welcome
9.2 out of 10, Wonderful, (39)
"The listing shows multiple beds in one room. The room had a pull out couch bed and all other beds were mattresses stored in garage and basement areas. We were very cramped with 7 guys trying to sleep. Photos appeared to be a much newer place."
☆BackYard BBQ Hidden Gem☆Perfect Location~Groups /Pets Welcome
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 AU$282
per night
9 May - 10 May
Classic FoxPark King 3BR w/ Deck
Property grounds
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 AU$236
per night
5 May - 6 May
StL's ‘The Hill' NBHD. Famous for all things Italian. Cozy & clean 2nd fl apt.
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
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.

Chesterfield Holiday Home Travel Info

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, (1002)
"the price beyond expected. will consider it again when come back to st louis."
The price is AU$178
per night
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, (1006)
"Drury Plaza Chesterfield is always a great place to stay, friendly staff & very clean. The breakfast & kickback with 3 free drinks is a bonus. My friends & I stay here every year & its always a great experience. "
The price is AU$220
per night
5 May - 6 May
Drury Plaza Hotel St. Louis Chesterfield
Exterior
Hyatt Place St. Louis/Chesterfield
3.0 star property
9.6 out of 10, Exceptional, (1001)
"Friendly staff. Top floor quiet"
The price is AU$266
per night
14 May - 15 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.

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, 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 favourite 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 depend 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 AU$207 per night. Entering your travel dates in the search wizard might find you 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.

Recent reviews of Chesterfield properties
Expedia verified reviews