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Compare 10 B&B in Chesterfield with updated reviews, rates, and availability.

The Lodge at Grant's Trail

3.5 star property
9.6 out of 10, Exceptional, (402)
"This place is awesome! I can’t wait to come back!"
The price is $157
includes taxes & fees
$136 per night
May 15 - May 16
The Lodge at Grant's Trail

Benton Park Inn

3.5 star property
9.6 out of 10, Exceptional, (279)
"We had a wonderful stay! Host was friendly and had great suggestions for dining and activities. The house was absolutely charming! Will definitely stay again."
The price is $143
includes taxes & fees
$122 per night
May 15 - May 16
Benton Park Inn

The Daniel Boone Room -Marthasville,MO

8.0 out of 10, Very Good, (2)
"We enjoyed the property. The decor is great and very clean. Location and hospitality was nice. "
The price is $158
includes taxes & fees
$146 per night
May 1 - May 2
The Daniel Boone Room -Marthasville,MO

Charming, Historic Family Suite, Steps from the Chase Park Plaza and Forest Park

10.0 out of 10, Exceptional, (3)
"This was a sweet space for us to relax and celebrate time with friends. Anthony was very helpful and cool. "
The price is $406
includes taxes & fees
$370 per night
May 5 - May 6
Charming, Historic Family Suite, Steps from the Chase Park Plaza and Forest Park

Central West End B&B

3.5 star property
7.8 out of 10, Good, (53)
"Really enjoyed the comfort. I would recommend this place to anyone. Very nice breakfast also!!! "
The price is $191
includes taxes & fees
$163 per night
May 4 - May 5
Central West End B&B

TheOutPostInn Bed&Breakfast - The Blue Victorian

10.0 out of 10, Exceptional, (3)
"Stayed in Hermann one night and here one night. Great space, comfy bed, quiet area."
The price is $183
includes taxes & fees
$169 per night
May 1 - May 2
TheOutPostInn Bed&Breakfast - The Blue Victorian

The Wineaux! Wine Country charm in Marthasville,MO

9.2 out of 10, Wonderful, (7)
"We loved the location and historic building there was no breakfast as promised and rooms were not ready when we got there at 4."
The price is $239
includes taxes & fees
$220 per night
May 1 - May 2
The Wineaux! Wine Country charm in Marthasville,MO

The Cyclist! Katy Trail comfort in Marthasville,MO

9.8 out of 10, Exceptional, (7)
"Wonderful place to get away to and relax!"
The price is $239
includes taxes & fees
$220 per night
May 1 - May 2
The Cyclist! Katy Trail comfort in Marthasville,MO

TheOutPostInn Bed&Breakfast - The Purple Victorian

6.0 out of 10, (1)
"It was a small room and had to squeeze between the bed and wall to get in. Almost had to use the foot stool to get in the bed secondary to being so high up and the mattress was extremely firm. The pillows were super soft which did not go with the firm bed, woke up several times in the night to re fluff the pillows and still woke up with a sore neck. The thing that bothered me the most was the curtain in the bathroom was screwed to the wall and you could not close them for privacy. The building...
The price is $203
includes taxes & fees
$188 per night
May 1 - May 2
TheOutPostInn Bed&Breakfast - The Purple Victorian
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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Other property types in Chesterfield

White House at Grand Central

4.0 star property
8.6 out of 10, Excellent, (104)
"Our stay was very home-like, safe, and comfortable."
The price is $172
includes taxes & fees
$147 per night
May 5 - May 6
White House at Grand Central

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

10.0 out of 10, Exceptional, (200)
"This property is within easy walking distance to ALL of historic downtown St Charles. It's obvious the owners take great care in keeping The Guest House in perfect condition, with every possible amenity provided. Very comfortable stay. We'll absolutely be back!"
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!

Funky mini loft in fox park! Pet friendly!!

7.8 out of 10, Good, (56)
"This place is INCREDIBLE!!! We have little kids, a teenager, a senior and two adults in the family and EVERYONE absolutely LOVED it! We can't wait to go back! This will definitely be our go to spot when visiting St Louis. The host was extremely communicative. There was plenty of space for everyone. It is decorated incredibly, everyone got a kick out of it! "
The price is $156
includes taxes & fees
$145 per night
May 7 - May 8
Funky mini loft in fox park! Pet friendly!!
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

What is the nightly rate for a Bed & Breakfast in Chesterfield?
Prices for B&Bs in Chesterfield often vary, but you can find a great deal from $143 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Chesterfield B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in Chesterfield?
The best time to book a B&B in Chesterfield is during the late spring to early summer months, particularly from May to July. This period marks the peak travel season, when visitors flock to the area to enjoy the vibrant local culture, outdoor activities, and temperate climate. With temperatures generally ranging from the mid-50s to the high 80s Fahrenheit, Chesterfield becomes a haven for those who appreciate leisurely strolls through its picturesque parks and charming streets.

July stands out as the most popular month, offering a lively atmosphere filled with community events and festivals. Whether you’re exploring the local farmer’s markets or taking part in outdoor concerts, there’s always something happening that caters to a variety of interests. The warm weather enhances outdoor adventures, making it an ideal time for hiking, biking, or simply enjoying a picnic in one of the many scenic spots.

If you’re looking for a more budget-friendly experience, consider visiting in November. During this month, you can enjoy the peaceful ambiance of Chesterfield as the crowds thin out, allowing for a more intimate exploration of the area’s historical sites and natural beauty. The crisp fall air and changing leaves provide a beautiful backdrop for your adventures.
What is the difference between a Chesterfield B&B and a hotel?
Every Chesterfield B&B has its own unique feel. Whether it’s a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Chesterfield B&Bs.