Chesterfield Holiday Rentals

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Our top choices for Chesterfield holiday rentals

Serenity Log Inn -Log out and Log Inn to Serenity

Serenity Log Inn -Log out and Log Inn to Serenity
Imperial
10.0 out of 10, Exceptional, (38 reviews)
"Everything exceeded our expectations, host was very accommodating, would definitely stay again."
United States
dennis m.
The price is NZ$324
includes taxes & fees
31 Mar - 1 Apr
Serenity Log Inn -Log out and Log Inn to Serenity

Charming Tower Grove Flat-Steps to T.G Park+Grand

Charming Tower Grove Flat-Steps to T.G Park+Grand
Tower Grove East
9.4 out of 10, Exceptional, (14 reviews)
"Great place to stay for long work trip"
United States
Kalee E.
The price is NZ$310
includes taxes & fees
1 Apr - 2 Apr
Charming Tower Grove Flat-Steps to T.G Park+Grand

Adorable Augusta Cabin

Adorable Augusta Cabin
Augusta
8.4 out of 10, Very good, (15 reviews)
"The cabin was adorable, everything was exactly the way the website stated, and we enjoyed a wonderful weekend. We already discussed coming back! "
United States
Michelle K.
The price is NZ$366
includes taxes & fees
31 Mar - 1 Apr
Adorable Augusta Cabin

Walk to Bars & Dining: Historic Benton Park Gem

Walk to Bars & Dining: Historic Benton Park Gem
3.0 star property
Benton Park
The price is NZ$583
includes taxes & fees
31 Mar - 1 Apr
Walk to Bars & Dining: Historic Benton Park Gem

Garden style studio @ Forest Park & City!

Garden style studio @ Forest Park & City!
Dogtown
8.0 out of 10, Very good, (22 reviews)
"Very cute and cozy. Nice to be close to everything. "
United States
Dhgirlie H.
The price is NZ$244
includes taxes & fees
31 Mar - 1 Apr
Garden style studio @ Forest Park & City!

Convenience 2 Bedroom House to Explore All of St Louis

Convenience 2 Bedroom House to Explore All of St Louis
University City
9.8 out of 10, Exceptional, (43 reviews)
"Place was clean and host was accommodating."
United States
Timothy M.
The price is NZ$465
includes taxes & fees
31 Mar - 1 Apr
Convenience 2 Bedroom House to Explore All of St Louis

Quaint Studio in STL Central!

Quaint Studio in STL Central!
Dogtown
8.2 out of 10, Very good, (24 reviews)
"Quaint apartment with all the amenities you would need for a weekend trip."
United States
Tirzah W.
The price is NZ$244
includes taxes & fees
4 Apr - 5 Apr
Quaint Studio in STL Central!

Cozy Historic WashMo home

Cozy Historic WashMo home
Washington
9.2 out of 10, Wonderful, (27 reviews)
"Lovely stay, well done on the updates of the house. Upstairs is a little cold, but otherwise it was a great weekend rental. Close to the river, so easy walking "
United States
Valerie R.
The price is NZ$486
includes taxes & fees
6 Apr - 7 Apr
Cozy Historic WashMo home

Cozy Soulard Getaway

Cozy Soulard Getaway
Soulard
9.2 out of 10, Wonderful, (42 reviews)
"The host was accommodating and the amenities is expected. The location was centrally located for us and the area is quiet. Would love to stay on my next visit "
United States
CLARISSA W.
The price is NZ$403
includes taxes & fees
31 Mar - 1 Apr
Cozy Soulard Getaway

Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi

Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi
Bevo Mill
9.2 out of 10, Wonderful, (20 reviews)
"This was exactly what were we looking for on our trip to St. Louis."
United States
Michelle O.
The price is NZ$396
includes taxes & fees
12 Apr - 13 Apr
Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
The Hill
9.8 out of 10, Exceptional, (172 reviews)
"Easy access and great location. Place was kept very clean. "
United States
Andrew P.
The price is NZ$265
includes taxes & fees
31 Mar - 1 Apr
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!

Centrally located in the Tower Grove East neighborhood!

Centrally located in the Tower Grove East neighborhood!
Tower Grove East
9.8 out of 10, Exceptional, (146 reviews)
"We enjoyed our stay! Very nice!!"
United States
Pam L.
The price is NZ$267
includes taxes & fees
1 Apr - 2 Apr
Centrally located in the Tower Grove East neighborhood!

Irises at TG Park | Fenced Backyard+W/D+Storage

Irises at TG Park | Fenced Backyard+W/D+Storage
Tower Grove South
9.2 out of 10, Wonderful, (13 reviews)
"It was a very nice place, lovely in decoration. Good communication. "
United States
Paula D.
The price is NZ$416
includes taxes & fees
2 Apr - 3 Apr
Irises at TG Park | Fenced Backyard+W/D+Storage

Augusta Studio at Halcyon Spa Bed & Breakfast

Augusta Studio at Halcyon Spa Bed & Breakfast
3.0 star property
Augusta
10.0 out of 10, Exceptional, (1 review)
"Everything was great with this place"
United States
Cynthia
Augusta Studio at Halcyon Spa Bed & Breakfast

Starry Night | Steps to Tower Grove Park

Starry Night | Steps to Tower Grove Park
Tower Grove South
9.8 out of 10, Exceptional, (30 reviews)
"The apartment was very clean and comfortable with a great location."
United States
Paul C.
The price is NZ$295
includes taxes & fees
14 Apr - 15 Apr
Starry Night | Steps to Tower Grove Park

Pet and kid friendly duplex with 2 bedrooms

Pet and kid friendly duplex with 2 bedrooms
Pacific
9.6 out of 10, Exceptional, (47 reviews)
"Such a wonderful weekend. We had everything we needed. Lovely spot! Thank you"
United States
Anonymous traveller
Pet and kid friendly duplex with 2 bedrooms

Soulard King 1BR - Personal Gym and Sauna Oasis

Soulard King 1BR - Personal Gym and Sauna Oasis
Soulard
10.0 out of 10, Exceptional, (9 reviews)
"Great location"
United States
Bridget R.
The price is NZ$315
includes taxes & fees
14 Apr - 15 Apr
Soulard King 1BR - Personal Gym and Sauna Oasis

Elegance in the STL Arch!

Elegance in the STL Arch!
Dogtown
7.6 out of 10, Good, (21 reviews)
"Listing was consistent with images and the price and location were great. Apartment was clean but furniture and linens are worn. There were only 3 towels and we stayed several days so that was a challenge. Location made up for that mostly as we walked to the zoo and forest park easily. My biggest complaint was the apartment smelled strongly of smoke. I don’t think anyone lives there so that was unusual to me, but there were several cigarette butts on the stairs and back porch nearby and we saw a...
United States
Michelle
Elegance in the STL Arch!

Chic Minimalist Gem w/ Fenced Backyard + W/D

Chic Minimalist Gem w/ Fenced Backyard + W/D
Princeton Heights
9.8 out of 10, Exceptional, (11 reviews)
"Clean, very comfortable apartment in a great location: easy walk to restaurants, coffee shops, Francis Park. Attractive, quiet, tree-lined neighborhood. Would definitely stay here again!"
United States
Jack S.
The price is NZ$352
includes taxes & fees
1 Apr - 2 Apr
Chic Minimalist Gem w/ Fenced Backyard + W/D

Stay on Main Historic Studio

Stay on Main Historic Studio
St. Charles Historic District
9.0 out of 10, Wonderful, (33 reviews)
"Nice property.. Clean. "
United States
Belinda J.
The price is NZ$340
includes taxes & fees
31 Mar - 1 Apr
Stay on Main Historic Studio
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.
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Top Chesterfield Hotel Reviews

Find out more about Chesterfield

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 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 NZ$233 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 Sophia M. Sachs Butterfly House, 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?

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!: This holiday home rental outside of Chesterfield is located in the city centre, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Chesterfield?

Choose from 4 Expedia holiday rentals in Chesterfield for a memorable holiday.

What can I see and do in Chesterfield?

Family-friendly attractions include Sky Zone Indoor Trampoline Park - St. Louis and Myseum, whereas Missouri River and Sophia M. Sachs Butterfly House are a couple of great spots to enjoy the outdoors. Other places in town to visit include The Factory and St. Louis Premium Outlets.

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.