Hot Chesterfield Cottage Rates

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Featured Cottages in Chesterfield

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

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

St. Charles
With a stay at this cottage, you'll be centrally located in St. Charles, a 3-minute drive from Ameristar Casino St. Charles and 7 minutes from Hollywood Casino ...
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!
Quaint St Louis Home ~ 6 Mi to Downtown!

Quaint St Louis Home ~ 6 Mi to Downtown!

3 out of 5
St. Louis
With a stay at this cottage in St. Louis, you'll be within a 10-minute drive of St. Louis Union Station and Forest Park.
Quaint St Louis Home ~ 6 Mi to Downtown!
Beautiful Cottage on Large one Acre Private Lot

Beautiful Cottage on Large one Acre Private Lot

Eureka
With a stay at this cottage in Eureka, you'll be within a 15-minute drive of Six Flags St. Louis and Big River.
Beautiful Cottage on Large one Acre Private Lot
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Dock & Resort Perks: Quiet Lakefront Cottage

Dock & Resort Perks: Quiet Lakefront Cottage

Innsbrook
Located in Innsbrook, this cottage is on a lake, within a 5-minute walk of Aspen Lake and South Mooring Marina.
Dock & Resort Perks: Quiet Lakefront Cottage
Historic headquarters of city founder! Gated parking!

Historic headquarters of city founder! Gated parking!

Saint Charles
With a stay at this cottage in St. Charles (St. Charles Historic District), you'll be a 2-minute drive from Ameristar Casino St. Charles and 6 minutes from Hollywood ...
Historic headquarters of city founder! Gated parking!
9 Mi to Dtwn: Vibrant St Louis Home!

9 Mi to Dtwn: Vibrant St Louis Home!

3 out of 5
St. Louis
With a stay at this cottage in St. Louis, you'll be within a 15-minute drive of St. Louis Union Station and Enterprise Center.
9 Mi to Dtwn: Vibrant St Louis Home!
Hound Haus - Dog Friendly, near Purina Farms and WashMO

Hound Haus - Dog Friendly, near Purina Farms and WashMO

Villa Ridge
Located in Villa Ridge, this cottage is in a rural location, within a 5-minute drive of Villa West Center and Shaw Nature Reserve.
Hound Haus - Dog Friendly, near Purina Farms and WashMO
Serene Pacific Getaway: Deck, Grill & Fire Pit!

Serene Pacific Getaway: Deck, Grill & Fire Pit!

3 out of 5
Pacific
With a stay at this cottage in Pacific, you'll be within a 15-minute drive of Six Flags St. Louis and Shaw Nature Reserve.
Serene Pacific Getaway: Deck, Grill & Fire Pit!
The Reubling House - Modern-rustic Cabin!

The Reubling House - Modern-rustic Cabin!

3 out of 5
Defiance
With a stay at this cottage in Defiance, you'll be steps from Yellow Farmhouse Winery and a 3-minute drive from Sugar Creek Winery.
The Reubling House - Modern-rustic Cabin!
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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 Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Chesterfield will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Chesterfield definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Chesterfield, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Chesterfield Cottages essential information

Accommodation
48 Cottages
Lowest Price
AU$173
Highest Price
AU$234
Popular accommodation
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!, Quaint St Louis Home ~ 6 Mi to Downtown!, Beautiful Cottage on Large one Acre Private Lot, Dock & Resort Perks: Quiet Lakefront Cottage, Historic headquarters of city founder! Gated parking!, 9 Mi to Dtwn: Vibrant St Louis Home!, Hound Haus - Dog Friendly, near Purina Farms and WashMO, Serene Pacific Getaway: Deck, Grill & Fire Pit!, The Reubling House - Modern-rustic Cabin!

Top trending hotels in Chesterfield

Sonesta ES Suites St. Louis - Chesterfield

Sonesta ES Suites St. Louis - Chesterfield

3 out of 5
15431 Conway Rd, Chesterfield, MO
Fully refundableReserve now, pay when you stay
The price is AU$173 per night from 2 Jan to 3 Jan
AU$173
includes taxes & fees
2 Jan - 3 Jan 2025
With a stay at Sonesta ES Suites St. Louis - Chesterfield in Chesterfield, you'll be in the suburbs, within a 15-minute drive of Hollywood Casino Amphitheatre ...
Sonesta ES Suites St. Louis - Chesterfield
Drury Plaza Hotel St. Louis Chesterfield

Drury Plaza Hotel St. Louis Chesterfield

3 out of 5
355 Chesterfield Ctr, Chesterfield, MO
Fully refundableReserve now, pay when you stay
The price is AU$234 per night from 29 Dec to 30 Dec
AU$234
includes taxes & fees
29 Dec - 30 Dec
With a stay at Drury Plaza Hotel St. Louis Chesterfield in Chesterfield, you'll be within a 15-minute drive of Hollywood Casino Amphitheatre and Chesterfield ...
Drury Plaza Hotel St. Louis Chesterfield
DoubleTree by Hilton Hotel St. Louis - Chesterfield

DoubleTree by Hilton Hotel St. Louis - Chesterfield

4 out of 5
16625 Swingley Ridge Rd, Chesterfield, MO
Fully refundableReserve now, pay when you stay
The price is AU$219 per night from 17 Jan to 18 Jan
AU$219
includes taxes & fees
17 Jan - 18 Jan 2025
With a stay at DoubleTree by Hilton Hotel St. Louis - Chesterfield in Chesterfield, you'll be 6.4 mi (10.3 km) from St. Louis Premium Outlets and 10.4 mi (16.8 ...
DoubleTree by Hilton Hotel St. Louis - Chesterfield
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Hyatt Place St. Louis/Chesterfield

Hyatt Place St. Louis/Chesterfield

3 out of 5
333 Chesterfield Center East, Chesterfield, MO
Fully refundableReserve now, pay when you stay
The price is AU$221 per night from 29 Dec to 30 Dec
AU$221
includes taxes & fees
29 Dec - 30 Dec
Located in Chesterfield, Hyatt Place St. Louis/Chesterfield is in the business district, within a 15-minute drive of Hollywood Casino Amphitheatre and Westport ...
Hyatt Place St. Louis/Chesterfield
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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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^Subject to availability and chosen travel dates.