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Holiday Homes in Chesterfield

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Holiday Homes in Chesterfield

Our top choices for Chesterfield holiday homes

St. Charles 1860's Gem - Sleeps 6!
Fridge, microwave, oven, stovetop

St. Charles 1860's Gem - Sleeps 6!

9.8 out of 10, Exceptional, (119)
"Everything was great!"
The price is AU$346
includes taxes & fees
25 Aug - 26 Aug
St. Charles 1860's Gem - Sleeps 6!
Beautiful, Rehabbed Unit in Shaw Community 4228a
Fridge, microwave, oven, stovetop

Beautiful, Rehabbed Unit in Shaw Community 4228a

7.6 out of 10, Good, (17)
"Very clean Spacious Beds were comfy "
The price is AU$419
includes taxes & fees
1 Sept - 2 Sept
Beautiful, Rehabbed Unit in Shaw Community 4228a
St Louis Townhome-Perfect for Groups!
Fridge, microwave, oven, stovetop

St Louis Townhome-Perfect for Groups!

8.0 out of 10, Very good, (53)
"My family had a great time staying in the town house for a quick, one night visit to St. Louis to see a Cardinals game. Great location close to Grove neighborhood and light rail access to downtown for Busch stadium. The town house is spacious, comfortable, and super clean. Highly recommend!"
The price is AU$375
includes taxes & fees
24 Aug - 25 Aug
St Louis Townhome-Perfect for Groups!
Historic*Unique*Downtown*Quiet*Bright*Cheerful*Getaway
Dining

Historic*Unique*Downtown*Quiet*Bright*Cheerful*Getaway

9.6 out of 10, Exceptional, (44)
"Lovely stay, very sweet house in a cute neighborhood. Great for traveling with kids! Thank you!"
The price is AU$460
includes taxes & fees
25 Aug - 26 Aug
Historic*Unique*Downtown*Quiet*Bright*Cheerful*Getaway
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, (208)
"Very nice and comfy home. Enjoyed our time and the hosts were great. "
Entire Dogtown House near Zoo, Forest Park and Wash U
Modern House with Terrace Near Forest Park
Property grounds

Modern House with Terrace Near Forest Park

9.0 out of 10, Wonderful, (11)
"This was perfect for 6. Close to a park with short running loop. Quaint shops with restaurants nearby. Would definitely stay here again!"
Modern House with Terrace Near Forest Park
Centrally located in the Tower Grove East neighborhood!
Interior

Centrally located in the Tower Grove East neighborhood!

9.8 out of 10, Exceptional, (125)
"Thoroughly enjoyed staying here. My sister and I were in town for an event and staying here made it even more fun!"
The price is AU$272
includes taxes & fees
24 Aug - 25 Aug
Centrally located in the Tower Grove East neighborhood!
Stunning 1890's Home - Sleeps 8!
Microwave, oven, stovetop, dishwasher

Stunning 1890's Home - Sleeps 8!

10.0 out of 10, Exceptional, (73)
"The house is beautiful, in a great location, and has all the amenities of home. Definitely glad we stayed here instead of a nearby hotel."
The price is AU$621
includes taxes & fees
2 Sept - 3 Sept
Stunning 1890's Home - Sleeps 8!
Charming 3-bedroom house with WiFi, AC in the heart of St. Louis
Exterior

Charming 3-bedroom house with WiFi, AC in the heart of St. Louis

2.0 star property
8.4 out of 10, Very good, (18)
"This was a great location. Perfect for our small group of friends. Very clean, easy check in. Very old house but done well. Would recommend. "
The price is AU$491
includes taxes & fees
25 Aug - 26 Aug
Charming 3-bedroom house with WiFi, AC in the heart of St. Louis
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, (146)
"This was a gem! So glad I booked this property and would highly recommend to any friends or family."
The price is AU$224
includes taxes & fees
26 Aug - 27 Aug
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
3BR Dogtown Bungalow |Office + Bar
Property grounds

3BR Dogtown Bungalow |Office + Bar

9.6 out of 10, Exceptional, (24)
"Pretty spacious house, nice quiet neighborhood with dining options within walking distance. "
The price is AU$537
includes taxes & fees
15 Sept - 16 Sept
3BR Dogtown Bungalow |Office + Bar
AK's STL Pearl Grey House - Game Room
Fridge, microwave, oven, stovetop

AK's STL Pearl Grey House - Game Room

9.0 out of 10, Wonderful, (7)
"Quiet neighborhood, comfortable house, well-stocked kitchen. We would stay here again."
The price is AU$786
includes taxes & fees
10 Sept - 11 Sept
AK's STL Pearl Grey House - Game Room
Honky Tonk Hideaway
Outdoor dining

Honky Tonk Hideaway

9.2 out of 10, Wonderful, (5)
"Great place to stay"
Honky Tonk Hideaway
STL, Tower Grove, Cozy 2-Story Townhome - A
4 bedrooms, iron/ironing board, WiFi, bed sheets

STL, Tower Grove, Cozy 2-Story Townhome - A

8.8 out of 10, Excellent, (22)
"Dan was a wonderful host and we enjoyed our stay. Very prompt response too!"
The price is AU$373
includes taxes & fees
1 Sept - 2 Sept
STL, Tower Grove, Cozy 2-Story Townhome - A
1870's Luxury Guest Cottage, Historic Downtown St. Charles, Mo.
Exterior

1870's Luxury Guest Cottage, Historic Downtown St. Charles, Mo.

10.0 out of 10, Exceptional, (261)
"Place was beautiful and had everything we needed! Would absolutely stay again "
1870's Luxury Guest Cottage, Historic Downtown St. Charles, Mo.
Tamm Ave 3-BR Retreat
Dining

Tamm Ave 3-BR Retreat

9.6 out of 10, Exceptional, (40)
"We stayed in St. Louis to visit the arch with our kids. The location was great with kids to be able to visit other surrounding attractions. We enjoyed our stay!"
Tamm Ave 3-BR Retreat
The St. Charles Guest House, lovely historic home, fun for families and groups
Outdoor dining

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

10.0 out of 10, Exceptional, (132)
"We very much enjoyed the property and location. "
The St. Charles Guest House, lovely historic home, fun for families and groups
Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi
Fridge, microwave, oven, stovetop

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

8.8 out of 10, Excellent, (14)
"Home was clean and conveniently located to our event. "
The price is AU$299
includes taxes & fees
24 Aug - 25 Aug
Charming 2-bedroom, cozy bungalow with sunroom in fabulous St. Louis with WiFi
beautiful small house
Fridge, microwave, oven, stovetop

beautiful small house

9.4 out of 10, Exceptional, (63)
"We completely enjoyed our stay at this location. We would book it again if we are in the area "
beautiful small house
House in Soulard near Downtown, Arch, Busch Stadium and anheuser busch brewery
Fridge, microwave, oven, stovetop

House in Soulard near Downtown, Arch, Busch Stadium and anheuser busch brewery

10.0 out of 10, Exceptional, (53)
"This home was in a great location. It was clean and very nicely decorated. The host was very responsive. We would definitely stay here again. It is close to so many good restaurants and places to visit in St. Louis. The neighborhood is so quaint too. "
The price is AU$354
includes taxes & fees
22 Aug - 23 Aug
House in Soulard near Downtown, Arch, Busch Stadium and anheuser busch brewery
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

Pear Tree Inn St. Louis Airport

Pear Tree Inn St. Louis Airport

10/10 Excellent
"Needed the available shuttle . Very nice to have . "
Julie 1-night trip
Posted 13 hours ago
Pear Tree Inn St. Louis Airport