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Chesterfield Holiday Rentals

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49 rentals in Chesterfield.
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Coco Channel, holiday rental in Chesterfield

Coco Channel

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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4 Bedroom Centrally Located West St Louis County, holiday rental in Chesterfield

4 Bedroom Centrally Located West St Louis County

4 bedrooms
2 bathrooms
Sleeps 8
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Perfect for your vacation stay in Historic St. Charles! Near Main Street, holiday rental in Chesterfield

Perfect for your vacation stay in Historic St. Charles! Near Main Street

3 bedrooms
2 bathrooms
Sleeps 6
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Charming house minutes away from downtown Kirkwood, holiday rental in Chesterfield

Charming house minutes away from downtown Kirkwood

3 bedrooms
2 bathrooms
Sleeps 6
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Amazing 1860's Historic Home!, holiday rental in Chesterfield

Amazing 1860's Historic Home!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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1920's Vintage Home in Historic Saint Charles - Fully Remodeled, holiday rental in Chesterfield

1920's Vintage Home in Historic Saint Charles - Fully Remodeled

3 bedrooms
2 bathrooms
Sleeps 8
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Gorgeous, Spacious, 4 Bedroom - Great Location!, holiday rental in Chesterfield

Gorgeous, Spacious, 4 Bedroom - Great Location!

4 bedrooms
3 bathrooms
Sleeps 8
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West County Gem - Easy access to STL attractions!, holiday rental in Chesterfield

West County Gem - Easy access to STL attractions!

3 bedrooms
2 bathrooms
Sleeps 8
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Clark Brick House w/ Pool - Historic St. Charles, holiday rental in Chesterfield

Clark Brick House w/ Pool - Historic St. Charles

3 bedrooms
3 bathrooms
Sleeps 9
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Vintage French Beauty - Newly Renovated & Spacious, holiday rental in Chesterfield

Vintage French Beauty - Newly Renovated & Spacious

3 bedrooms
2 bathrooms
Sleeps 8
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Residence on the Roundabout, holiday rental in Chesterfield

Residence on the Roundabout

2 bedrooms
1 bathroom
Sleeps 4
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St. Charles 1860's Gem - Sleeps 8!, holiday rental in Chesterfield

St. Charles 1860's Gem - Sleeps 8!

2 bedrooms
1 bathroom
Sleeps 8
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Huge Renovated Historic Schoolhouse w/Hidden Room!, holiday rental in Chesterfield

Huge Renovated Historic Schoolhouse w/Hidden Room!

4 bedrooms
3 bathrooms
Sleeps 12
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The Bungalow Walkout, holiday rental in Chesterfield

The Bungalow Walkout

1 bedroom
1 bathroom
Sleeps 4
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Special July pricing! ~Great location book now~ C, holiday rental in Chesterfield

Special July pricing! ~Great location book now~ C

3 bedrooms
1 bathroom
Sleeps 6
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Quiet St Charles Cottage w/ Patio & 4 Acres, holiday rental in Chesterfield

Quiet St Charles Cottage w/ Patio & 4 Acres

2 bedrooms
2 bathrooms
Sleeps 8
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Historic Farmhouse Wine Escape: Walk to Katy Trail, holiday rental in Chesterfield

Historic Farmhouse Wine Escape: Walk to Katy Trail

2 bedrooms
2 bathrooms
Sleeps 4
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Backyard BBQ Hidden Gem~Groups/Kids/Pets Welcome, holiday rental in Chesterfield

Backyard BBQ Hidden Gem~Groups/Kids/Pets Welcome

4 bedrooms
2 bathrooms
Sleeps 16
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Special Mar pricing! ~Great location book now~ T, holiday rental in Chesterfield

Special Mar pricing! ~Great location book now~ T

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy, Romantic, Rooftop Living, holiday rental in Chesterfield

Cozy, Romantic, Rooftop Living

1 bedroom
1 bathroom
Sleeps 3
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Lovely condo fully remodeled just minutes from West Port Plaza, holiday rental in Chesterfield

Lovely condo fully remodeled just minutes from West Port Plaza

2 bedrooms
1 bathroom
Sleeps 4
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updated 1 bedroom condo in secure building, holiday rental in Chesterfield

updated 1 bedroom condo in secure building

1 bedroom
1 bathroom
Sleeps 2
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All new cozy Guest Nest Luxe (Unit A), holiday rental in Chesterfield

All new cozy Guest Nest Luxe (Unit A)

2 bedrooms
1 bathroom
Sleeps 4
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All New Cozy Guest Nest home mins from the airport -Extended Stay  (Unit B), holiday rental in Chesterfield

All New Cozy Guest Nest home mins from the airport -Extended Stay (Unit B)

2 bedrooms
1 bathroom
Sleeps 4
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Da Lux, holiday rental in Chesterfield

Da Lux

2 bedrooms
1 bathroom
Sleeps 4
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The brick and Morgan: History Meets Modern Brick Home in St. Charles near Main, holiday rental in Chesterfield

The brick and Morgan: History Meets Modern Brick Home in St. Charles near Main

2 bedrooms
1 bathroom
Sleeps 6
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French Town St. Charles. Walk to Main St/MO River, holiday rental in Chesterfield

French Town St. Charles. Walk to Main St/MO River

3 bedrooms
2 bathrooms
Sleeps 16
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CLEAN St. Charles Central Oasis*Pets/kids/Groups/2 CAR Garage, holiday rental in Chesterfield

CLEAN St. Charles Central Oasis*Pets/kids/Groups/2 CAR Garage

4 bedrooms
3 bathrooms
Sleeps 16
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Lindenwood campus-Fenced BckYrd-Near Main St, holiday rental in Chesterfield

Lindenwood campus-Fenced BckYrd-Near Main St

3 bedrooms
2 bathrooms
Sleeps 16
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Large, Spacious, Clean, Family Friendly, Self Check in, Free Garage Parking,, holiday rental in Chesterfield

Large, Spacious, Clean, Family Friendly, Self Check in, Free Garage Parking,

2 bedrooms
1 bathroom
Sleeps 4
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NEW! 'The Ruebling House' Historic Defiance Apt!, holiday rental in Chesterfield

NEW! 'The Ruebling House' Historic Defiance Apt!

3 bedrooms
1 bathroom
Sleeps 6
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NEW! 'The Ruebling House' Bright + Modern Abode!, holiday rental in Chesterfield

NEW! 'The Ruebling House' Bright + Modern Abode!

3 bedrooms
1 bathroom
Sleeps 6
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NEW! ‘The Ruebling House’ Cozy 2nd-Floor Apartment, holiday rental in Chesterfield

NEW! ‘The Ruebling House’ Cozy 2nd-Floor Apartment

2 bedrooms
2 bathrooms
Sleeps 6
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2 homes just 2 blocks from main street. Large covered Pavillion fully furnished, holiday rental in Chesterfield

2 homes just 2 blocks from main street. Large covered Pavillion fully furnished

5 bedrooms
3 bathrooms
Sleeps 23
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ReNew Centennial Suites, holiday rental in Chesterfield

ReNew Centennial Suites

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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St Platinum Peaceful Homestay, holiday rental in Chesterfield

St Platinum Peaceful Homestay

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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NEW! ‘Bross Brother's Cabin’ w/ Wraparound Porch!, holiday rental in Chesterfield

NEW! ‘Bross Brother's Cabin’ w/ Wraparound Porch!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Inviting Weekend Getaway in Clayton with Pool *Weekly Discounts*, holiday rental in Chesterfield

Inviting Weekend Getaway in Clayton with Pool *Weekly Discounts*

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Student Housing w/ Self Check In *Weekly Discounts*, holiday rental in Chesterfield

Charming Student Housing w/ Self Check In *Weekly Discounts*

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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University City Apartment + Restaurants Nearby *Weekly Discounts*, holiday rental in Chesterfield

University City Apartment + Restaurants Nearby *Weekly Discounts*

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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St. Louis Sanctuary near Parks & WASHU *Weekly Discounts*, holiday rental in Chesterfield

St. Louis Sanctuary near Parks & WASHU *Weekly Discounts*

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Quiet Housing with Clubhouse + Gym *Weekly Discounts*, holiday rental in Chesterfield

Quiet Housing with Clubhouse + Gym *Weekly Discounts*

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy and Comfortable Vector Guest Suite *Weekly Discounts*, holiday rental in Chesterfield

Cozy and Comfortable Vector Guest Suite *Weekly Discounts*

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Relaxing St. Louis Getaway + Pool *Weekly Discounts*, holiday rental in Chesterfield

Relaxing St. Louis Getaway + Pool *Weekly Discounts*

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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University City Apt. in Quiet Neighborhood *Weekly Discounts*, holiday rental in Chesterfield

University City Apt. in Quiet Neighborhood *Weekly Discounts*

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Comfy Modern Suite in Heart of Clayton *Weekly Discounts*, holiday rental in Chesterfield

Comfy Modern Suite in Heart of Clayton *Weekly Discounts*

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious 2 BD Just Outside DTL Clayton *Weekly Discounts*, holiday rental in Chesterfield

Spacious 2 BD Just Outside DTL Clayton *Weekly Discounts*

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Pet-Friendly St Louis Home w/ Private Yard!, holiday rental in Chesterfield

NEW! Pet-Friendly St Louis Home w/ Private Yard!

1 bedroom
2 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Newly Renovated Home Near Dtwn & Katy Trail!, holiday rental in Chesterfield

NEW! Newly Renovated Home Near Dtwn & Katy Trail!

3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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