House vacation rentals in Chesterfield

Find and book unique houses on Airbnb

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Popular amenities for Chesterfield house rentals

House rentals with a pool

Guest favorite

Home in Ballwin

4.95 out of 5 average rating, 126 reviews

Private indoor pool & sauna

PamRating, 5 stars1 month ago
We enjoyed a long family weekend at Deborah’s home, conveniently a two hour drive for all of us. The grandkids (four - ages 4-7) were excited about the pool and delighted with all the toys and games in the house. Deborah really does an outstanding job making guests feel welcome and was responsive to queries. The house is a very nice and spacious mid-century home with a well stocked kitchen. Plenty of towels and bedding. We had a great time and appreciate Deborah’s thoughtfulness as a host.
Guest favorite

Home in Saint Charles

4.92 out of 5 average rating, 152 reviews

Clark Brick House w/ Pool | Historic St. Charles

BrianRating, 5 stars6 days ago
Dylan was a fantastic host with a # of restaurant recommendations, and he shipped my daughter's Apple Watch to us after she left it behind in on e of the rooms. Would definitely stay here again! Thank you for the hospitality!!
Guest favorite

Home in Creve Coeur

4.96 out of 5 average rating, 49 reviews

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

OrvellaRating, 5 stars1 week ago
The house was large, beautiful, and met all of our needs perfectly! I'm incredibly particular about cleanliness, and this place exceeded my expectations - everything was spotlessly clean and well-maintained. The location was fantastic, being centrally located to restaurants, convenience stores, grocery stores, and pretty much anywhere we needed to go. The hosts did an amazing job with this property, and I will definitely stay here or at another one of their properties in the future.
Superhost

Home in Washington

5 out of 5 average rating, 7 reviews

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

KristinaRating, 5 stars4 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 favorite

Home in Dittmer

4.95 out of 5 average rating, 433 reviews

Honeymoon Suite Camp Skullbone In The Woods

KimberlyRating, 5 stars3 weeks ago
absolutely gorgeous inside and out. very peaceful stay and the hot tub was amazing right outside the door. hiked the property and it was very interesting, the creek runs through and the rock hounding was awesome. can't wait to go back . going to book this every time I come to visit my kids. Id stay with them but this is so fun ! communication with my host was superb .
Guest favorite

Home in Gray Summit

4.88 out of 5 average rating, 144 reviews

Sunset Mountain Privacy

HeatherRating, 5 stars2 weeks ago
The beautiful house has a gorgeous view and a fantastic floor plan. It has excellent decor and a good number of amenities. I will return in the warmer months to spend more time outside and enjoy all this home offers. The best thing was the stocked kitchen; if things had been different, I would have enjoyed making some meals.
Superhost

Home in St. Louis

4.8 out of 5 average rating, 81 reviews

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

LoganRating, 5 stars2 months ago
Erik's place is why I still love Airbnb. You want places with features you aren't going to find anywhere else and this property goes well beyond the expected here. Can't recommend enough.
Superhost

Home in Warrenton

4.82 out of 5 average rating, 39 reviews

The Hiding Place - Private Pool and Spa, sleeps 16

RachelRating, 5 stars2 weeks 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 favorite

Home in Ballwin

5 out of 5 average rating, 19 reviews

Perfect Getaway 3BR/3BA Home

SusanRating, 5 stars3 weeks ago
I had a wonderful stay at this Airbnb! The space was incredibly clean, welcoming, and comfortable. The beds were cozy with soft sheets, and the towels were top-notch. I especially appreciated how well-stocked the home was, with everything you could need readily available. The thoughtful labeling throughout made it so easy to find things like remote controls, towels, and kitchenware without any confusion. This attention to detail truly enhanced the experience. I highly recommend this place for anyone looking for a hassle-free, relaxing stay! Thank you. We had a wonderful stay
Superhost

Home in Marthasville

5 out of 5 average rating, 4 reviews

HappyApples BicycleBunkhouse-WholeHouse-Sleeps 23

EmilyRating, 5 stars5 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 favorite

Home in St. Louis

5 out of 5 average rating, 9 reviews

Beautiful 1B/1BA Bungalow House*Central Locale*W/D

DavidRating, 5 stars19 months ago
Well appointed, clean and comfortable space that’s close to so many great attractions in St Louis! Would stay again!
Guest favorite

Home in St. Louis

4.83 out of 5 average rating, 187 reviews

Beautiful and Spacious 3BR Newly Renovated Home

NancyRating, 5 stars3 weeks ago
We arrived in St. Louis to another rental and soon learned it was infested with mice. We contacted Amie about her place and she accepted our last minute booking pronto. We so appreciate her efforts to accommodate us! The house is absolutely beautiful and the neighborhood is quiet, with friendly neighbors. I plan to stay with Amie again on our next trip to St. Louis.
Guest favorite

Home in Marthasville

5 out of 5 average rating, 51 reviews

Relax and Recharge in a farm experience.

LeaRating, 5 stars1 month ago
A great place to stay with tons of walking trails (one has a waterfall!) and adorable animals to interact with. They provide treats to feed the donkeys, sheep, fish, and dogs. It’s fun to take the golf cart all around the property and enjoy the peacefulness of the area. Their property is so beautiful and well kept. John is one of the nicest people I’ve ever met!
Guest favorite

Home in The Hill

4.99 out of 5 average rating, 164 reviews

Spacious Bungalow on "The Hill"

GarrettRating, 5 stars1 week ago
Thank you all for a cozy stay on the hill. And for the nice coffee setup and momento!
Guest favorite

Home in The Hill

4.79 out of 5 average rating, 100 reviews

Fragola House

SarahRating, 5 stars2 weeks ago
This place was perfect for my family. It had everything we needed. Heather was super friendly and responsive.
Guest favorite

Home in St. Louis

4.91 out of 5 average rating, 181 reviews

Luxurious 5BR Home. Rooftop Deck with Arch views!

CainRating, 5 stars3 months ago
Amazing stay amazing home with amazing views of the city.

Private house rentals

Superhost

Home in Tower Grove South

4.87 out of 5 average rating, 110 reviews

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

DillonRating, 5 stars2 months ago
Edward was a great host! The place was clean and tidy, he was amazing at communicating and even reached out during our stay the see how we were! I forgot my wallet at the airbnb, he picked it up for me and offered to mail it even. Would give Edward a 6/5 stars if I could!
Guest favorite

Home in Saint Charles

4.96 out of 5 average rating, 78 reviews

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

DavidRating, 5 stars3 weeks ago
Beautiful house. Clean and very functional. Highly recommend.
Guest favorite

Home in St. Louis

4.83 out of 5 average rating, 18 reviews

Private 2 Bedroom 1 Bath House

MicahRating, 5 stars1 month ago
The stay was fantastic! The property was clean, well-maintained, and exactly as described in the listing. The host was incredibly friendly and responsive, making sure I had everything I needed. The location was perfect, with easy access to local attractions. Highly recommend and would definitely stay again!
Guest favorite

Home in Soulard

5 out of 5 average rating, 32 reviews

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

GregRating, 5 stars3 weeks ago
Katie & Tyler were great host - very responsive and provide great suggestions. Since we were making Thanksgiving dinner they brought over some additional kitchen items that were helpful. Everything is exactly as you see in the pictures and they have added lots on info on the house and Soulard area. Great experience overall
Guest favorite

Home in St. Louis

4.92 out of 5 average rating, 370 reviews

Sunny South City Guest House

PeterRating, 5 stars1 week ago
The place was lovely and David was great to work with. He allowed great flexibility for check-in, really easy and fast communication. The only suggestion I made (to his mom, who came to clean when I checked out) was that a small desk to create a workspace would be a helpful addition. But I would absolutely stay here again and I give it a big thumbs-up.
Superhost

Home in St. Louis

4.85 out of 5 average rating, 61 reviews

Modern Luxury w/Saltwater Pool / ABODEbucks

AshleyRating, 5 stars2 weeks ago
Mary was amazing, very responsive. Amazing home. Would definitely stay here again. Loved it!
Guest favorite

Home in Saint Charles

4.88 out of 5 average rating, 82 reviews

Family/4bd/2bth/Huge Yard/Playset/Ping-Pong/Arcade

SallyRating, 5 stars2 days ago
This was an amazing stay. Airbnb showing of the house was excellent. Host was great. I would recommend this house. We were a party of 6 adults and 1 child. Plent of toys and activities for her to play with. It was a great stay and the price was excellent for the amenities. We couldn't get the add'l tvs to work. The main tv in the living was fine. This was a great place to stay. We were not traveling for pleasure but traveling due to a death in the immediate family. It was comforting at the end of long emotional days and we all felt 'at home'. Our sincerest thanks for Sarah to open up this home for us. I would highly recommend it.
Guest favorite

Home in Shiloh

5 out of 5 average rating, 24 reviews

Family House on the Christmas Tree Farm

HeatherRating, 5 stars9 months ago
My family and I felt at home . Very nice home and close to shopping. I would highly recommend.

Quick stats about house rentals in Chesterfield

  • Total rentals

    20 properties

  • Total number of reviews

    200 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

Destinations to explore