Chesterfield Holiday House Rentals from AU$359: Search Holiday Homes

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A town with a prominent church spire, residential buildings, and a hill in the background.

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Our top choices for Chesterfield holiday homes

A spacious living area with a high ceiling, wooden beams, a fireplace, a dining area, and a cozy seating arrangement.

A spacious living area with a wooden staircase, a leather sofa, a coffee table, and various decorative items.

A modern house with a koi pond, a waterfall, and a tree with red leaves.

A spacious living area with a wooden staircase, leather sofas, a fireplace, and a clock on the wall.

1. Private 3-Acre Retreat • Koi Pond & Waterfall

Private 3-Acre Retreat • Koi Pond & Waterfall

Wildwood

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"This is a beautiful home in a quiet beautiful setting. The host was great to work with and responded quickly to any questions we had. Would highly recommend!"

Jennifer M.

The price is AU$542

AU$542

includes taxes & fees

28 Sept - 29 Sept

Private 3-Acre Retreat • Koi Pond & Waterfall

A wooden-paneled room with a sofa, a small bedside table with a lamp, and a marble-patterned rug.

A wooden-paneled bedroom with a bed, bedside tables, a chair, and a ceiling fan.

A kitchen with wooden cabinets, a dishwasher, and a refrigerator.

A hallway with wooden flooring, white walls, and a door at the end.

2. The Knotty Pine House

The Knotty Pine House

Saint Charles

The price is AU$481

AU$481

includes taxes & fees

25 Sept - 26 Sept

The Knotty Pine House

A spacious living room with a fireplace, a ceiling fan, and a large window with shutters.

A compact kitchen with white cabinets, a refrigerator, and a dining table with chairs.

A compact kitchen with white cabinetry, a dining table with a white tablecloth, and a black chair.

3. Saint Charles White House

Saint Charles White House

Saint Charles

8.6 out of 10, Excellent, (7 reviews)

8.6/10

Excellent

(7 reviews)

"The host was a pleasure to work with and easy to talk to. "

Matthew M.

The price is AU$483

AU$483

includes taxes & fees

28 Sept - 29 Sept

Saint Charles White House

A modern kitchen with white cabinetry, a stainless steel range, and a built-in oven.

A hot tub in a wooden structure with a ceiling fan, a window, and a warning sign.

A modern kitchen with white cabinets, stainless steel appliances, and a dining area with brown leather chairs.

A modern kitchen with white cabinets, a double washer, and a large window.

4. The Chalet | St Charles 2BR Private Retreat on 1.2 Acres | By Mercer Stays

The Chalet | St Charles 2BR Private Retreat on 1.2 Acres | By Mercer Stays

Saint Charles

9.2 out of 10, Wonderful, (5 reviews)

9.2/10

Wonderful

(5 reviews)

"We loved the location for our travel needs and we had everything we needed for a family of two adults and two dogs. "

Leslie R.

The price is AU$914

AU$914

includes taxes & fees

19 Oct - 20 Oct

The Chalet | St Charles 2BR Private Retreat on 1.2 Acres | By Mercer Stays

A modern home office with a desk, chair, and computer monitor.

A compact laundry room with a washing machine, dryer, and a small table with a chair.

A room with a white door, a round table with two chairs, and a decorative wall piece above the table.

A modern kitchen with white cabinets, a stainless steel oven, and a microwave. There are two bar stools and a small table with a plant.

5. Spacious 2 Bedroom Townhome

Spacious 2 Bedroom Townhome

Saint Charles

8.0 out of 10, Very good, (19 reviews)

8.0/10

Very good

(19 reviews)

"Quiet area and clean rooms"

Chelsie H.

The price is AU$434

AU$434

includes taxes & fees

27 Sept - 28 Sept

Spacious 2 Bedroom Townhome

A modern living room with a grey sectional sofa, a wooden coffee table, and a staircase with wooden steps.

A modern living room with a grey sofa, a wooden coffee table, a TV mounted on the wall, and a kitchen visible through an open door.

A modern bedroom with a large bed, a flat-screen TV, a bedside table with a lamp, and a decorative fish tank.

A compact laundry room with a front-loading washer and dryer, wooden flooring, and a shelf above the dryer holding various items.

6. Near Streets of St Charles | 2 King Beds

Near Streets of St Charles | 2 King Beds

Saint Charles

9.0 out of 10, Wonderful, (12 reviews)

9.0/10

Wonderful

(12 reviews)

"We really enjoyed our stay. The house was clean, spacious, and very accommodating. We stayed for a dance competition and the proximity to the convention center was unbeatable. "

Chloe

The price is AU$442

AU$442

includes taxes & fees

28 Sept - 29 Sept

Near Streets of St Charles | 2 King Beds

A room with a sliding glass door leading to an outdoor patio with a table and chairs.

A living room with a sofa, coffee table, and patterned rug. There is a dining area with a bar and stools.

A grassy area with a pond, a wooden structure, and a fenced enclosure.

A two-story house with a patio area featuring outdoor furniture and string lights.

7. Private Entry Basement Suite • Pond & Farm View • Pet Friendly • St Peters

Private Entry Basement Suite • Pond & Farm View • Pet Friendly • St Peters

St. Peters

10.0 out of 10, Exceptional, (16 reviews)

10/10

Exceptional

(16 reviews)

"Excellent place to stay while visiting. Pet friendly a HUGE plus. The host was very pleasant to work with and the place really is thoughtfully outfitted. Would definitely stay here again"

Chris B.

The price is AU$412

AU$412

includes taxes & fees

18 Oct - 19 Oct

Private Entry Basement Suite • Pond & Farm View • Pet Friendly • St Peters

A modern living room with a dark gray sectional sofa, a glass coffee table, and a staircase with wooden steps leading to an upper level.

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

A neatly made bed with a tray of towels, a bedside table with a lamp, and two framed artworks on the wall.

A modern living room with a sectional sofa, a coffee table, and a window with blinds.

8. St. Charles Townhome | 2 Kings, Walkable

St. Charles Townhome | 2 Kings, Walkable

Saint Charles

8.8 out of 10, Excellent, (10 reviews)

8.8/10

Excellent

(10 reviews)

"Very comfortable bed and pillows. Coffee was there when we woke up- everything provided."

Barbara T.

The price is AU$445

AU$445

includes taxes & fees

30 Sept - 1 Oct

St. Charles Townhome | 2 Kings, Walkable

A staircase with white steps and black handrails, leading to a landing with a black railing.

A modern kitchen with grey cabinets, a black stove, and a microwave.

A modern living room with a sectional sofa, a wooden coffee table, and a small side table with a lamp.

A modern living room with a wooden desk, a yellow chair, a TV mounted on the wall, and a kitchen visible through an open doorway.

9. Dog-Friendly 2BR | Near Streets of St Charles

Dog-Friendly 2BR | Near Streets of St Charles

Saint Charles

9.0 out of 10, Wonderful, (19 reviews)

9.0/10

Wonderful

(19 reviews)

"Wish we would have had more time to stay a little longer. Will definitely stay again in the future!"

Rebecca O.

The price is AU$445

AU$445

includes taxes & fees

27 Sept - 28 Sept

Dog-Friendly 2BR | Near Streets of St Charles

A modern kitchen with white cabinets, a black refrigerator, and a central island.

A two-story house with a front porch, a stone retaining wall, and a black street lamp.

A bed with a quilted white bedspread, a wooden headboard, and a bedside table with a lamp and remote control.

A kitchen with a refrigerator, stove, and bar stools.

10. Cottage on Main st- Low Cleaning Fee

Cottage on Main st- Low Cleaning Fee

St. Charles Historic District

10.0 out of 10, Exceptional, (10 reviews)

10/10

Exceptional

(10 reviews)

"Good location. Decorated very nicely. "

Debbie A.

The price is AU$407

AU$407

includes taxes & fees

6 Oct - 7 Oct

Cottage on Main st- Low Cleaning Fee

A living room with a sofa, armchairs, a coffee table, a lamp, a ceiling fan, and a rug.

A Christmas tree with blue and white ornaments, placed on a blue rug with white trim.

A living room with a sofa, a patterned rug, a dining table with chairs, and a green door.

A bedroom with a bed, a bedside table with a plant, a ceiling fan, a wardrobe, and a television.

11. Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!

Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!

St. Charles Historic District

9.6 out of 10, Exceptional, (86 reviews)

9.6/10

Exceptional

(86 reviews)

"Quaint and quiet, with easy access to downtown St Charles."

Jeffrey E.

The price is AU$361

AU$361

includes taxes & fees

27 Sept - 28 Sept

Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!

A compact kitchen with a refrigerator, washer, and dryer, wooden flooring, and a window with blinds.

A dining table with a marble top, surrounded by leather chairs. A vase with flowers is placed on the table.

A wooden deck with a white railing, two black chairs, and a view of a green landscape with trees.

12. Charming 3-bedroom house in delightful Ballwin and basement is not included

Charming 3-bedroom house in delightful Ballwin and basement is not included

Ballwin

7.2 out of 10, Good, (7 reviews)

7.2/10

Good

(7 reviews)

"House is located in quiet neighborhood. As described with 3 bedrooms 1 bath. Had adequate towels and supplies in kitchen. Cleanish, was not sure if sheets had been cleaned. Overall, a decent place to stay."

Stephanie N.

The price is AU$1,047

AU$1,047

includes taxes & fees

25 Sept - 26 Sept

Charming 3-bedroom house in delightful Ballwin and basement is not included

A living room with a gray sectional sofa, a wooden coffee table, and a patterned rug.

A spacious living room with a wooden dining table, gray sofas, and a TV.

A modern kitchen with white cabinets, a stainless steel microwave, a gas stove, and a granite countertop.

A bedroom with a large bed, a wooden headboard, a ceiling fan, a wall-mounted abstract art piece, and a bedside table with a lamp.

13. 5th Street #1 · Historic 5th Street House - Fully Rehabbed # 1

5th Street #1 · Historic 5th Street House - Fully Rehabbed # 1

St. Charles Historic District

8.8 out of 10, Excellent, (16 reviews)

8.8/10

Excellent

(16 reviews)

"House was beautiful. Very nice quiet stay"

Amy S.

The price is AU$359

AU$359

includes taxes & fees

27 Sept - 28 Sept

5th Street #1 · Historic 5th Street House - Fully Rehabbed # 1

A spacious kitchen with white cabinets, a central island with bar stools, a stainless steel refrigerator, and a microwave.

A spacious living area with a grey sectional sofa, a wooden floor, a staircase, and a kitchen in the background.

A two-story house with a garage, a front yard, and a driveway.

14. Spacious, 3 bedroom home, finished basement on quiet court

Spacious, 3 bedroom home, finished basement on quiet court

St. Peters

9.8 out of 10, Exceptional, (55 reviews)

9.8/10

Exceptional

(55 reviews)

"It was a perfect choice for our family to celebrate Christmas. "

Leanne S.

Spacious, 3 bedroom home, finished basement on quiet court

A compact kitchen with white cabinets, a stainless steel refrigerator, a coffee maker, and a hanging pendant light.

A dining area with a wooden table, chairs, and a chandelier. A kitchen is visible in the background.

A bedroom with a bed, a television mounted on the wall, a door, and a hallway leading to another room.

A bathroom with a mirror, towel rack, and a shower area.

15. Convenience 2 Bedroom House to Explore All of St Louis

Convenience 2 Bedroom House to Explore All of St Louis

University City

10.0 out of 10, Exceptional, (52 reviews)

10/10

Exceptional

(52 reviews)

"The house was immaculately clean and beds were extremely comfortable!"

Anna M.

The price is AU$377

AU$377

includes taxes & fees

28 Sept - 29 Sept

Convenience 2 Bedroom House to Explore All of St Louis

A living room with a fireplace, a television, and a sofa.

A modern living room with a flat-screen TV, a white coffee table, and a grey sofa.

An aerial view of a residential area with houses, lawns, and a road.

16. Beautiful 4-bedroom house Central to St. Louis and St. Charles

Beautiful 4-bedroom house Central to St. Louis and St. Charles

St. Louis

8.4 out of 10, Very good, (38 reviews)

8.4/10

Very good

(38 reviews)

"Good price for a four bedroom home."

BRAD R.

The price is AU$492

AU$492

includes taxes & fees

13 Oct - 14 Oct

Beautiful 4-bedroom house Central to St. Louis and St. Charles

A modern living room with a fireplace, two armchairs, a small table, and decorative plants.

A modern living room with a green sofa set, a coffee table, and a dining area with a table and chairs. There is a staircase leading to another level, a large window with a view of greenery, and a welcome sign on the wall.

A dining area with a round table and four chairs, a black brick backsplash, and a chandelier.

A modern living room with a large green sofa, a coffee table, and a fireplace. There is a 'welcome' sign on the wall and a window with a view of trees.

17. The Reunion House | St Charles 4BR Sleeps 14 Game Room Hot Tub | Mercer Stays

The Reunion House | St Charles 4BR Sleeps 14 Game Room Hot Tub | Mercer Stays

Saint Charles

9.8 out of 10, Exceptional, (7 reviews)

9.8/10

Exceptional

(7 reviews)

"Such a perfect place to stay for a weekend with a larger group! Close to a lot of different things and had pretty much everything you could need. It was also super clean and nice! "

Amanda P.

The price is AU$1,454

AU$1,454

includes taxes & fees

27 Sept - 28 Sept

The Reunion House | St Charles 4BR Sleeps 14 Game Room Hot Tub | Mercer Stays

A living room with a flat-screen TV, a sofa with patterned cushions, a coffee table, and a rug.

A living room with a ceiling fan, a sofa, a chair, a TV, and a door.

A bed with a tufted headboard, multiple pillows, a bedside table, a lamp, and a window with curtains.

18. Cottage on Historic Main Street- Low Cleaning fee

Cottage on Historic Main Street- Low Cleaning fee

St. Charles Historic District

10.0 out of 10, Exceptional, (23 reviews)

10/10

Exceptional

(23 reviews)

"Great location to Main Street. "

Daneen H.

Cottage on Historic Main Street- Low Cleaning fee

A hallway with a wooden wall, a door leading to a bedroom, and a staircase.

A bedroom with a large bed, a bedside table, a lamp, and a window with blinds.

A modern living room with a green sofa, a wooden coffee table, a brick wall, and a ceiling fan.

A laundry room with a white cabinet and shelves holding folded towels.

19. St. Charles 1860's Gem - Sleeps 6!

St. Charles 1860's Gem - Sleeps 6!

St. Charles Historic District

9.8 out of 10, Exceptional, (164 reviews)

9.8/10

Exceptional

(164 reviews)

"Very nice very clean property. Very much enjoyed our stay"

Joe R.

The price is AU$393

AU$393

includes taxes & fees

27 Sept - 28 Sept

St. Charles 1860's Gem - Sleeps 6!

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

Renaissance St. Louis Airport Hotel

10/10 Excellent

"We had a great experience at the hotel. The Internet you do have to pay extra for if you hook up your devices. Also parking is about $25 a night before taxes. All and all a good experience"

Johnathan 2-night trip

Posted 3 hours ago

Renaissance St. Louis Airport Hotel