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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Tonight
16 Apr - 17 Apr
Tomorrow
17 Apr - 18 Apr
This weekend
18 Apr - 20 Apr
Next weekend
25 Apr - 27 Apr

Holiday Rentals in Chesterfield

White House at Grand Central
Individually decorated, individually furnished, desk, laptop workspace

White House at Grand Central

4.0 star property
8.6 out of 10, Excellent, (103)
"Very enjoyable old building, nice location by campus and walk to theaters, m short drive to forrest park, museums. Hot water was limited and free parking 10 minute walk away, otherwise nice place. "
The price is HK$789
HK$1,421 total
includes taxes & fees
21 Apr - 22 Apr
White House at Grand Central
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!
Exterior

1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!

10.0 out of 10, Exceptional, (199)
"My husband and I stayed two nights at this cottage and loved it so much. It’s super cute and cozy, perfect for just the two of us. And you can’t beat the location! Within walking distance to everything on Main Street. My husband said he wanted to stay here again!"
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!
Funky mini loft in fox park! Pet friendly!!
Private kitchen

Funky mini loft in fox park! Pet friendly!!

7.8 out of 10, Good, (54)
"Overall it was good, though the cleaning prior to us could've been better. Someones leftover over in a room, cobwebs, and dead bugs under one of the beds.Fun and easy place otherwise. "
The price is HK$465
HK$1,078 total
includes taxes & fees
23 Apr - 24 Apr
Funky mini loft in fox park! Pet friendly!!
☆BackYard BBQ Hidden Gem☆Perfect Location~Groups /Pets Welcome
Pool

☆BackYard BBQ Hidden Gem☆Perfect Location~Groups /Pets Welcome

9.0 out of 10, Wonderful, (46)
"Great stay with family! "
The price is HK$1,698
HK$3,332 total
includes taxes & fees
20 Apr - 21 Apr
☆BackYard BBQ Hidden Gem☆Perfect Location~Groups /Pets Welcome
Value Suites Extended Stay - St Louis
Desk, laptop workspace, blackout curtains, WiFi

Value Suites Extended Stay - St Louis

3.0 star property
7.0 out of 10, Good, (1110)
"It was okay"
The price is HK$716
HK$1,466 total
includes taxes & fees
20 Apr - 21 Apr
Value Suites Extended Stay - St Louis
Beautiful, Rehabbed Unit in Shaw Community 4228a
Fridge, microwave, oven, stovetop

Beautiful, Rehabbed Unit in Shaw Community 4228a

10.0 out of 10, Exceptional, (3)
"Very clean Spacious Beds were comfy "
The price is HK$349
HK$2,076 total
includes taxes & fees
20 Apr - 21 Apr
Beautiful, Rehabbed Unit in Shaw Community 4228a
Beautiful Tower Grove Unit, Recently Renovated 2S
Fridge, microwave, oven, stovetop

Beautiful Tower Grove Unit, Recently Renovated 2S

8.8 out of 10, Excellent, (36)
"Nice location and clean! Would definitely stay here again."
The price is HK$659
HK$1,994 total
includes taxes & fees
2 May - 3 May
Beautiful Tower Grove Unit, Recently Renovated 2S
StL's ‘The Hill' NBHD. Famous for all things Italian. Cozy & clean 2nd fl apt.
Terrace/patio

StL's ‘The Hill' NBHD. Famous for all things Italian. Cozy & clean 2nd fl apt.

10.0 out of 10, Exceptional, (253)
"Great location in The Hill. Close to everything we wanted to see and do. Comfortable bed. Water pressure is weak but everything else was great. Responsive owners. "
The price is HK$589
HK$1,155 total
includes taxes & fees
29 Apr - 30 Apr
StL's ‘The Hill' NBHD. Famous for all things Italian. Cozy & clean 2nd fl apt.
Large Executive 1st Floor Apartment with Chefs Kitchen!
Living area

Large Executive 1st Floor Apartment with Chefs Kitchen!

9.0 out of 10, Wonderful, (6)
"The property was well equipped, very clean, and an absolute joy to stay in."
Large Executive 1st Floor Apartment with Chefs Kitchen!
The St. Charles Guest House, lovely historic home, fun for families and groups
Exterior

The St. Charles Guest House, lovely historic home, fun for families and groups

10.0 out of 10, Exceptional, (124)
"We very much enjoyed the property and location. "
The St. Charles Guest House, lovely historic home, fun for families and groups
275 On The Park - Senate Apartments By Barsala
Property amenity

275 On The Park - Senate Apartments By Barsala

4.0 star property
6.8 out of 10, (5)
".absolutely love it clean house nice area very close to town highly recommend most def will book if visiting St Louis again"
The price is HK$580
HK$1,586 total
includes taxes & fees
23 Apr - 24 Apr
275 On The Park - Senate Apartments By Barsala
Spacious 3-Bedroom with King Bed
Living area

Spacious 3-Bedroom with King Bed

4.0 star property
9.6 out of 10, Exceptional, (5)
"Nice large apartment for a family trip! Only concern was broken glass on the patio-we chose not to use the patio because of this. I minor issue but it should be addressed. "
Spacious 3-Bedroom with King Bed
St. Charles 1860's Gem - Sleeps 6!
Fridge, microwave, oven, stovetop

St. Charles 1860's Gem - Sleeps 6!

9.8 out of 10, Exceptional, (94)
"Loves it"
The price is HK$892
HK$1,885 total
includes taxes & fees
21 Apr - 22 Apr
St. Charles 1860's Gem - Sleeps 6!
Modern House with Terrace Near Forest Park
Property grounds

Modern House with Terrace Near Forest Park

8.6 out of 10, Excellent, (4)
"The check in, the space, everything was amazing. We will be back to this place again. There is a park within walking distance that was GREAT to get our kids "zoomies" out. Thank you so much. I do think someone before us stole pot holders - we could not find any. We got the cookies out with a rag! Thank you again!"
Modern House with Terrace Near Forest Park
Amazing Soulard STL Unit, 713a
Fridge, microwave, oven, stovetop

Amazing Soulard STL Unit, 713a

2.0 star property
8.4 out of 10, Very good, (14)
"Owner of this property is amazingly nice and quick with communication. Property is older but in good condition. Worked well for our stay! "
The price is HK$380
HK$1,536 total
includes taxes & fees
20 Apr - 21 Apr
Amazing Soulard STL Unit, 713a
Authentic Log cabin with something for everyone!
Exterior

Authentic Log cabin with something for everyone!

9.6 out of 10, Exceptional, (354)
"Really enjoyed the space, loved having the lake in the backyard."
Authentic Log cabin with something for everyone!
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (131)
"We had a wonderful night in St. Louis"
The price is HK$659
HK$1,109 total
includes taxes & fees
20 Apr - 21 Apr
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
beautiful small house
2 bedrooms, iron/ironing board, travel cot, free WiFi

beautiful small house

9.4 out of 10, Exceptional, (52)
"Was in town for battlehawks game for the weekend. It was perfect homebase for the game and great location everything was close by."
beautiful small house
Entire Dogtown House near Zoo, Forest Park and Wash U
Exterior

Entire Dogtown House near Zoo, Forest Park and Wash U

10.0 out of 10, Exceptional, (200)
"Perfect weekend stay for our family of four (3 and 1 year old). Close to the zoo, house and as very clean, and overall great location in STL"
Entire Dogtown House near Zoo, Forest Park and Wash U
The Lofts of North Main Street
Fridge, microwave, oven, stovetop

The Lofts of North Main Street

9.6 out of 10, Exceptional, (128)
"The loft was gorgeous and so clean! Quiet and cozy ! Will definitely be back! "
The price is HK$1,000
HK$2,015 total
includes taxes & fees
29 Apr - 30 Apr
The Lofts of North Main Street
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.
Don't see what you're looking for?
See all available properties in Chesterfield
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Chesterfield you may be interested in

Sonesta ES Suites St. Louis - Chesterfield
Seasonal outdoor pool

Sonesta ES Suites St. Louis - Chesterfield

3.0 star property
8.0 out of 10, Very good, (1000)
"Condo style "
The price is HK$721
HK$836 total
includes taxes & fees
29 Apr - 30 Apr
Sonesta ES Suites St. Louis - Chesterfield
Hyatt Place St. Louis/Chesterfield
Lobby

Hyatt Place St. Louis/Chesterfield

3.0 star property
9.6 out of 10, Exceptional, (1001)
"Good location. Good restaurant close by."
The price is HK$985
HK$1,143 total
includes taxes & fees
27 Apr - 28 Apr
Hyatt Place St. Louis/Chesterfield
Drury Plaza Hotel St. Louis Chesterfield
Exterior

Drury Plaza Hotel St. Louis Chesterfield

3.0 star property
9.6 out of 10, Exceptional, (1002)
"Definitely enjoyed my stay!"
The price is HK$1,008
HK$1,169 total
includes taxes & fees
20 Apr - 21 Apr
Drury Plaza 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.

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?

☆BackYard BBQ Hidden Gem☆Perfect Location~Groups /Pets Welcome: This holiday home rental outside of Chesterfield is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a private garden and a selection of games.

How many holiday rentals are there in Chesterfield?

Choose from 11 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 Sophia M. Sachs Butterfly House and Missouri River are a couple of great spots to enjoy the outdoors. Other places in town to visit include Westfield Chesterfield Mall and The Factory.

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.