House holiday rentals in Chesterfield

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Chesterfield

House rentals with a pool

Guest favourite
Home in Ballwin
4.95 out of 5 average rating, 128 reviews

Private indoor pool & sauna

LindsayRating, 5 stars2 weeks ago
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.
Superhost
Home in Lake Saint Louis
5 out of 5 average rating, 3 reviews

Lake St. Louis Luxury Get-a-Way

Justin And MykaylaRating, 5 stars10 months ago
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.
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 stars3 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, 57 reviews

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

NickRating, 5 stars1 week ago
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.
Guest favourite
Home in Washington
5 out of 5 average rating, 7 reviews

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

KristinaRating, 5 stars7 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, 471 reviews

Honeymoon Suite Camp Skullbone In The Woods

MaryRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Gray Summit
4.89 out of 5 average rating, 158 reviews

Sunset Mountain Forest Privacy

JadenRating, 5 stars2 days ago
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!
Superhost
Home in St. Louis
4.79 out of 5 average rating, 86 reviews

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

CharlieRating, 5 stars1 month 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.

Weekly house rentals

Top guest favourite
Home in Ballwin
5 out of 5 average rating, 26 reviews

Perfect Getaway 3BR/3BA Home

KimberlyRating, 5 stars3 days ago
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.
Superhost
Home in Central West End
4.95 out of 5 average rating, 158 reviews

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

RobinRating, 5 stars1 month ago
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.
Superhost
Home in Marthasville
5 out of 5 average rating, 4 reviews

HappyApples BicycleBunkhouse-WholeHouse-Sleeps 23

EmilyRating, 5 stars9 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, 193 reviews

Beautiful and Spacious 3BR Newly Renovated Home

EmilyRating, 5 stars2 weeks ago
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!
Top guest favourite
Home in The Hill
4.99 out of 5 average rating, 171 reviews

Spacious Bungalow on "The Hill"

MaggieRating, 5 stars1 week ago
Perfect location and incredibly clean. Great spot for a solo traveler or couple
Guest favourite
Home in The Hill
4.8 out of 5 average rating, 111 reviews

Fragola House

JackieRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Fenton
4.88 out of 5 average rating, 40 reviews

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

DavidRating, 5 stars1 week ago
We really enjoyed our stay, very close to everything and overall a great experience.
Superhost
Home in Central West End
4.88 out of 5 average rating, 147 reviews

Amazing Vintage Mansion | Sleeps 16 / ABODEbucks

KathleenRating, 5 stars2 weeks ago
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

Superhost
Home in Tower Grove South
4.88 out of 5 average rating, 116 reviews

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

SimonRating, 5 stars3 weeks ago
Great stay! Cute house, cute neighborhood, great host. As advertised - I recommend.
Guest favourite
Home in Belleville
4.89 out of 5 average rating, 114 reviews

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

MaryRating, 5 stars1 week ago
Great comfortable house in Belleville, IL. Would definitely stay again if we are in town :)
Top guest favourite
Home in St. Louis
5 out of 5 average rating, 13 reviews

Home Sweet Fully-Furnished Home!

RomeshRating, 5 stars2 days ago
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.
Guest favourite
Home in St. Louis
4.85 out of 5 average rating, 20 reviews

Private 2 Bedroom 1 Bath House

JuliaRating, 5 stars3 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!
Top guest favourite
Home in Saint Charles
5 out of 5 average rating, 9 reviews

*NEW* La Maison Douceur in Historic St Charles

TarahRating, 5 stars1 day ago
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!
Top guest favourite
Home in Soulard
5 out of 5 average rating, 41 reviews

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

EmilyRating, 5 stars2 weeks ago
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!
Guest favourite
Home in St. Louis
4.91 out of 5 average rating, 395 reviews

Sunny South City Guest House

GabbyRating, 5 stars2 weeks ago
This place feels like a magical treehouse.
Guest favourite
Home in Alton
4.85 out of 5 average rating, 102 reviews

Backyard Seclusion Cottage

ErikRating, 5 stars2 weeks ago
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