
House holiday rentals in Chesterfield
Find and book unique houses on Airbnb
Top-rated house rentals in Chesterfield
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Chesterfield
House rentals with a pool

Private indoor pool & sauna
Deborah's house is a great alternative option to a hotel! We booked it for the private indoor pool and numerous positive reviews. We were not disappointed!! All of the kids and adults loved the pool, and Deborah had supplied an amazing array of pool toys, floaties, and towels. There were clear directions on how to get into and exit the pool area (there is an alarm for safety). The kids' rooms were made up in such a cute way (sheets, blankets, and decor), we were very appreciative of all the extra little things at the house for the kids, including snacks and treats, games, coloring books, playdoh, and toys. Also, Deborah was always quickly responsive to messages and clearly answered any questions we had. The kitchen is stocked with pretty much anything you need to cook, serve, and store food, and overall the house has everything you would need if you forget any toiletries at home.

Lake St. Louis Luxury Get-a-Way
One of the best stays I’ve had. Description says she shares the home so she may be there at times. Had I not known that I wouldn’t have known she was there as there is a separate space she stays in. Just a beautiful home great value. Thank you again.

Clark Brick House w/ Pool | Historic St. Charles
Very nice home and super clean we appreciate everything! Would definitely stay here again! Thank you for such a nice home.

Blair's Pool House - Creve Couer Hot Tub Game Room
We enjoyed our stay at this home which was in a wonderful neighborhood very close to many stores and restaurants. It was also close enough to St. Louis for easy commutes for day trips to downtown St. Louis. The home had a nice layout, was clean, and provided plenty of space for our family of 4. The host was very responsive and proactive.

Mill Haus - Heated Swimming Pool, Hot Tub, Dog Fri
Amazing experience. We had a girls trip planned and our other airbnb fell through at the last minute. Somehow, this home was still available and it really became a blessing in disguise! The home is absolutely gorgeous and the hosts are so so helpful! Answered every question I had before the trip very quickly. We had trouble connecting to the wifi and I sent the host a text and he called me right away to assure us he was on it and it was fixed within the hour! Would’ve loved to book this home again for my wedding but it’s already booked for that weekend.

Honeymoon Suite Camp Skullbone In The Woods
We loved our stay. The area is beautiful and so is the cabin - it was perfectly decorated. The price is amazing and with only staying one night, we appreciated the checkin and out hours. The cabin was spotless and had everything we needed. Stargazing from the hot tub made for an amazing evening. We would love to come back again!

Sunset Mountain Forest Privacy
rebecca’s place is definitely beautiful & felt very homey. she was very good with communication and was good with our privacy as well. i for sure recommend booking with her!

Pool/Speakeasy/Spaceship/Beach/pool/Costumes.
The place was the coolest house I have ever been too. So many cool features to explore. The host was also incredibly helpful and friendly with everything.
Weekly house rentals

Perfect Getaway 3BR/3BA Home
This house was so perfect for our family and our stay. We had our 3 adult children and 1 of their spouses and our baby granddaughter with us too. Since we were there for a hard, emotional time (funeral of my father-in-law), it was sooo much better to be in a house than at a hotel in separate rooms. So great to have a kitchen and plenty of space and 3 full bathrooms! When we return to St. Louis to visit again, I'd love to stay here again.

3,000 SF 4+ bdrm Private Home in Central West End
Property was clean. Great location. Ann was very helpful with questions I had prior to making my final selection. Our group was 13 adults and only one couple within the group and we were able to accommodate everyone comfortably.

HappyApples BicycleBunkhouse-WholeHouse-Sleeps 23
The house was as described and the perfect place to stay with our crew of 7 adults and 10 kids. The kids enjoyed the outside space and exploring the different bunk rooms.

Beautiful and Spacious 3BR Newly Renovated Home
This place was amazing I would definitely book again if I revisited the St.Louis area. Not only was it beautiful, clean and perfect but the hosts were also very communicative and responsive. Thank you so much for the perfect stay for our spring break family trip!

Spacious Bungalow on "The Hill"
Perfect location and incredibly clean. Great spot for a solo traveler or couple

Fragola House
A charming and cozy place to stay. We loved all of the little touches that made us feel at home. Most notably, the kitchen was clean, spacious, and stocked with everything we needed to prepare our meals. Heather was very friendly and accommodating for a special request we had. We had one issue that was beyond her control, and she handled it quickly and efficiently. We would definitely stay here again!

Valley - 9 Beds, 3 TVs, Sleeps 14 - Luxury Stay.
We really enjoyed our stay, very close to everything and overall a great experience.

Amazing Vintage Mansion | Sleeps 16 / ABODEbucks
I booked this property in the fall for a family wedding in the spring. The 5 pm check in tie was a surprise and caused us to rearrange our travel plans by one day …months before the actual booking,,, and I was still charged a fee even though the stay was for the same number of days. Chris claimed he could not override the fee. 5 pm is very late for check in especially in a transitional neighborhood.
Private house rentals

☆ Hot Tub ☆ New Renovated ☆ Massage Shower ☆Yard☆
Great stay! Cute house, cute neighborhood, great host. As advertised - I recommend.

Spacious 2/1 w/large yard only 20 min to STL Arch
Great comfortable house in Belleville, IL. Would definitely stay again if we are in town :)

Home Sweet Fully-Furnished Home!
The home was in excellent condition. Well stocked. Garrett was also very communicative and even offered to turn on the porch light for us when we were out late at night and did not turn it on. When a storm came through during our visit, he let us know, and was always trying to be helpful. If we are ever in the area again, we will certainly check to see if Garrett’s place is available. Highly recommended.

Private 2 Bedroom 1 Bath House
The listing is accurate and my expectations were met. The fridge water stopped working on the second day, but the host was very communicative and offered to have a maintenance person stop by, but we chose to decline (and they also dropped off some bottled waters which was unnecessary, but very nice). The location is very convenient to all of the places we needed to go. You can walk to Forest Park (fyi busy road with sidewalks), but it’s also a very quick drive!

*NEW* La Maison Douceur in Historic St Charles
The house was set up very well for families. The beds were comfortable, and the area had a lot of fun things to do. They had a great set up for our dog too!

The PS House: Hot Tub, Pool Table, Walk Score 93!
Katie and Tyler were amazing hosts, going the extra mile to accommodate our request at the last minute to stay at the PS House for our final night of a spring break vacation that had been interrupted by illness and an unexpected trip to the ER. After a long few days on the road this was the perfect place to unwind as a family. The kids loved the pool table. There are endless places to walk for restaurants and entertainment. The beds were so comfortable. The whole house and neighborhood had a great vibe and was beyond our expectations. We would love to stay again!

Sunny South City Guest House
This place feels like a magical treehouse.

Backyard Seclusion Cottage
Second time staying here, love Susan as a host and the place is amazing! Thanks again for a great visit Susan!
Quick stats about house rentals in Chesterfield
Total rentals
20 properties
Total number of reviews
230 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
Local attractions
St. Louis Premium Outlets, Chesterfield Mall and The Butterfly House
Destinations to explore
- St. Louis Holiday rentals
- Columbia Holiday rentals
- Springfield Holiday rentals
- Saint Charles Holiday rentals
- Hermann Holiday rentals
- Innsbrook Holiday rentals
- Jefferson City Holiday rentals
- Dolomiten Holiday rentals
- Quincy Holiday rentals
- Grafton Holiday rentals
- Nashville Holiday rentals
- Chicago Holiday rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Busch Stadium
- Enterprise Center
- Six Flags St. Louis
- Saint Louis Zoo
- Central West End
- Hidden Valley Ski Resort
- Gateway Arch National Park
- Missouri Botanical Garden
- City Museum
- St. Louis Aquarium at Union Station
- Saint Louis Science Center
- Meramec State Park
- Castlewood State Park
- Cuivre River State Park
- Adventure Valley Zipline Tours and Paintball Park
- Missouri History Museum
- Cathedral Basilica of Saint Louis
- Boone Valley Golf Club
- Pere Marquette State Park
- Bellerive Country Club
- The Winery at Aerie's Resort
- Raging Rivers WaterPark
- Grafton Winery the Vineyards
- Old Warson Country Club