House holiday rentals in Chesterfield

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Popular amenities for Chesterfield house rentals

House rentals with a pool

Guest favourite
Home in Ballwin
4.95 out of 5 average rating, 127 reviews

Private indoor pool & sauna

JoanRating, 5 stars1 week ago
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
Guest favourite
Home in Saint Charles
4.92 out of 5 average rating, 154 reviews

Clark Brick House w/ Pool | Historic St. Charles

MichelleRating, 5 stars2 months ago
Very nice home and super clean we appreciate everything! Would definitely stay here again! Thank you for such a nice home.
Guest favourite
Home in Creve Coeur
4.96 out of 5 average rating, 52 reviews

Blair's Pool House - Creve Couer Hot Tub Game Room

StephanieRating, 5 stars2 months ago
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.
Superhost
Home in Washington
5 out of 5 average rating, 7 reviews

Mill Haus - Heated Swimming Pool, Hot Tub, Dog Fri

KristinaRating, 5 stars6 months ago
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.
Guest favourite
Home in Dittmer
4.95 out of 5 average rating, 457 reviews

Honeymoon Suite Camp Skullbone In The Woods

RochelleRating, 5 stars4 weeks ago
The best getaway near St. Louis. This is our 6th trip and we always return.
Guest favourite
Home in Gray Summit
4.88 out of 5 average rating, 152 reviews

Sunset Mountain Privacy Retreat

LindseyRating, 5 stars1 week ago
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!
Superhost
Home in St. Louis
4.79 out of 5 average rating, 85 reviews

Pool/Speakeasy/Spaceship/Beach/pool/Costumes.

CharlieRating, 5 stars6 days ago
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.
Superhost
Home in Warrenton
4.82 out of 5 average rating, 39 reviews

The Hiding Place - Private Pool and Spa, sleeps 16

RachelRating, 5 stars3 months ago
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

Guest favourite
Home in Ballwin
5 out of 5 average rating, 23 reviews

Perfect Getaway 3BR/3BA Home

LaurieRating, 5 stars1 month ago
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!
Guest favourite
Home in Central West End
4.95 out of 5 average rating, 154 reviews

3,000 SF 4+ bdrm Private Home in Central West End

BridgetRating, 5 stars1 month ago
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!
Superhost
Home in Marthasville
5 out of 5 average rating, 4 reviews

HappyApples BicycleBunkhouse-WholeHouse-Sleeps 23

EmilyRating, 5 stars8 months ago
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.
Guest favourite
Home in St. Louis
4.83 out of 5 average rating, 191 reviews

Beautiful and Spacious 3BR Newly Renovated Home

PaulaRating, 5 stars1 month ago
Absolutely beautiful house accommodated our girls trip perfectly we will be back!!!
Guest favourite
Home in The Hill
4.99 out of 5 average rating, 167 reviews

Spacious Bungalow on "The Hill"

SpencerRating, 5 stars2 weeks ago
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!
Guest favourite
Home in The Hill
4.8 out of 5 average rating, 104 reviews

Fragola House

PamelaRating, 5 stars1 month ago
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
Guest favourite
Home in Fenton
4.86 out of 5 average rating, 37 reviews

Valley - 9 Beds, 3 TVs, Sleeps 14 - Luxury Stay.

MichaelRating, 5 stars2 months ago
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!
Superhost
Home in Central West End
4.88 out of 5 average rating, 145 reviews

Amazing Vintage Mansion | Sleeps 16 / ABODEbucks

DanielleRating, 5 stars1 week ago
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

Superhost
Home in Tower Grove South
4.88 out of 5 average rating, 114 reviews

☆ Hot Tub ☆ New Renovated ☆ Massage Shower ☆Yard☆

HeatherRating, 5 stars3 weeks ago
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!
Guest favourite
Home in Belleville
4.89 out of 5 average rating, 112 reviews

Spacious 2/1 w/large yard only 20 min to STL Arch

Shane-LindsayRating, 5 stars1 month ago
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.
Guest favourite
Home in Saint Charles
4.96 out of 5 average rating, 84 reviews

Old Charm on Fifth 4B 2.5B/ 10 Guests 5min to Main

JodiRating, 5 stars1 week ago
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!
Guest favourite
Home in St. Louis
4.85 out of 5 average rating, 20 reviews

Private 2 Bedroom 1 Bath House

JuliaRating, 5 stars2 months ago
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!
Guest favourite
Home in Marissa
4.96 out of 5 average rating, 26 reviews

The Old Homestead, an 1845 Mansion, modern.

RachelRating, 5 stars4 months ago
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.
Guest favourite
Home in Staunton
4.94 out of 5 average rating, 35 reviews

2br home, private yard hot tub

AndrewRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Soulard
5 out of 5 average rating, 38 reviews

The PS House: Hot Tub, Pool Table, Walk Score 93!

KaylaRating, 5 stars1 month ago
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!
Guest favourite
Home in St. Louis
4.91 out of 5 average rating, 386 reviews

Sunny South City Guest House

ShaneRating, 5 stars2 weeks ago
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

  • Wi-Fi availability

    20 properties include access to Wi-Fi

  • Popular amenities

    Kitchen, Wi-Fi and Pool

  • Local attractions

    St. Louis Premium Outlets, Faust Park and Chesterfield Mall

Destinations to explore