
House holiday rentals in Chesterfield
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Top-rated house rentals in Chesterfield
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Holiday rentals for every style
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Popular amenities for house rentals in Chesterfield
House rentals with a pool

Private indoor pool & sauna
The owner went above and beyond to make our stay wonderful. We were celebrating a birthday and she had birthday decorations and treats all over the house. We will definitely stay there 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
The house was perfect for our family. It had a great living room so that we could all be together hanging out. We would definitely rent it again.

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
The best getaway near St. Louis. This is our 6th trip and we always return.

Sunset Mountain Privacy Retreat
Appreciate Rebecca’s willingness to accommodate our checkin time and request to be left completely alone. Booking a shared space is usually a no-go for us, but in this case, Rebecca ensured we’d have complete privacy, and we didn’t regret it! Snacks on the table at checkin and a well-stocked kitchen and home were so inviting and appreciated—TY for a great stay, Rebecca!

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.

The Hiding Place - Private Pool and Spa, sleeps 16
The hiding place is a cute, historic home with enough bedrooms for our family Thanksgiving/Christmas with 10 adults and 6 kids. We booked this place because it was the most affordable option with as many bedrooms as we needed, and it ended up being a great find! We loved our stay! It is an old home with old home charm and quirks (don't put a level on the floor), but bathrooms are updated and the house was CLEAN! I can tell Robyn continues updating, because a new stove was installed right before our visit. Being an older home, it is not open concept, so there was no one room that fit everyone at the same time. This was really only a concern when we did our Christmas gift exchange. Some people stood in the doorways. Between the breakfast room and the dining room, there was the perfect separation for a kids table and an adult table for meals. The basement was a nice open space for the kids to play! Very easy access to I-70, but far away enough that it is definitely residential.
Weekly house rentals

Perfect Getaway 3BR/3BA Home
The house is very clean and spacious, which we appreciated for having 3 of us staying, and a few local family members over for a visit. It was great having the lower level for the little ones, and the kitchen with the island bar plus dining table made preparing and serving food very user friendly. We also appreciated the 3 bathrooms and garage. Most of all we appreciated the prompt and friendly responses to our questions. The location was excellent for proximity to our dad in a nearby hospital, and other siblings living locally. We all enjoyed the daily deer visits, too!

3,000 SF 4+ bdrm Private Home in Central West End
We are very appreciative of the host Ann, who was able to make her place available immediately for us when our original AirBnB cancelled our reservation at the last minute. The door code was provided within minutes of reaching out to Ann, and the house was perfect for our family gathering of 11. There was lots of a space, including a third floor with a bunch of bunk beds and a separate living room that was ideal for the kiddos in our group. The dining room had tables and chairs for our entire group to eat together. Everything, including the kitchen, was set up well and easy to find what we needed. The residential neighborhood had plenty of parking but there was also a car port for 2 cars. The back patio and yard seemed nice but it was too cold outside for us to use it. Overall great stay!

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
Absolutely beautiful house accommodated our girls trip perfectly we will be back!!!

Spacious Bungalow on "The Hill"
Had an absolute wonderful stay at Nancy's. The home is a cozy little spot right in the heart of The Hill. Short, enjoyable walks to many neighborhood locations and it is located on a very peaceful, quiet street. There was ample parking right in front of the home. I would recommend this location if you not only want to visit this historic neighborhood, but want to be within short distance of other St. Louis attractions. The host was helpful, attentive, and you can certainly see they take pride in keeping such a lovely home. I hope to return again soon!

Fragola House
We loved this roomy house with a great location for The Hill and WashU area! The living room and bed room had comfortable furniture for us to hang out in. We loved the kitchen with its strawberry decor and tasty snacks. My daughters loved the Keurig. We would definitely consider staying here again

Valley - 9 Beds, 3 TVs, Sleeps 14 - Luxury Stay.
Very responsive host. Our three year old loved the park, which was directly across the street. Our teenagers loved having their own space upstairs and in the basement. Exit instructions were simple - we will return!

Amazing Vintage Mansion | Sleeps 16 / ABODEbucks
Loved this house! The shower was incredible. Loved the location. Great sleeping options for big groups and I appreciated the quiet hours.
Private house rentals

☆ Hot Tub ☆ New Renovated ☆ Massage Shower ☆Yard☆
The hosts were the best at communication and helpfulness. extremely responsive and proactive. I loved the home and they had little snacks and things set up upon welcome which was a great touch and suprise. I would stay here again!

Spacious 2/1 w/large yard only 20 min to STL Arch
Nice little place that's away from the big city but still within a 20 minutes drive of most stuff. The entire back yard is fenced in which offers some privacy out back. The hosts were always quick to reply to messages and friendly. Would definitely stay here again if we were ever back in the area.

Old Charm on Fifth 4B 2.5B/ 10 Guests 5min to Main
Can't say enough! Absolutely lovely home. Spacious and just beautifully decorated. Amenities were FANTASTIC- we really appreciated the ease of having all you could need. Excellent location, close to shopping and great restaurants. Host was quick respond and very helpful. I would most definitely rent this property again!

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!

The Old Homestead, an 1845 Mansion, modern.
We have stayed at Jackie's homes many times now and have enjoyed it every time. It's the perfect place for family celebrations with room for all of us. We particularly love using the well-stocked kitchen to cook family meals even while far away from my own home.

2br home, private yard hot tub
Great home, great amenities. It is on a state road, so just be aware theres bound to be loads of crosswinds and sounds of trucks coming from the road while outside at the hottub (where it presently is as of 02/2025 anyhow) - but its easy to get over quick for us. Otherwise, it was disconnected enough for our lil staycation from St Louis.

The PS House: Hot Tub, Pool Table, Walk Score 93!
This place was the best place we have every stayed! We had the best weekend exploring Stl for my bachelorette trip. Beautiful place, safe neighborhood, and amazing host!

Sunny South City Guest House
The place was exactly as advertised, and I really appreciated the health and quantity of the plants. This place exceeded my expectations.
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, Faust Park and Chesterfield Mall
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