House holiday rentals in Chesterfield
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Top-rated house rentals in Chesterfield
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Chesterfield house rentals
House rentals with a pool
Home in Ballwin
4.95 out of 5 average rating, 126 reviewsPrivate indoor pool & sauna
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.
Home in Lake Saint Louis
5 out of 5 average rating, 3 reviewsLake 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.
Home in Saint Charles
4.92 out of 5 average rating, 153 reviewsClark Brick House w/ Pool | Historic St. Charles
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!!
Home in Creve Coeur
4.96 out of 5 average rating, 51 reviewsBlair's Pool House - Creve Couer Hot Tub Game Room
We had a wonderful stay here. Matt and Blair even allowed us to check in early, which was extremely helpful for our trip plans. We were traveling for medical purposes which meant most of our time was spent in the Airbnb. So it was important for us to have a very nice stay. Safe & quiet neighborhood. Great amenities. Loved the small touches that made our lives easier - lots of kitchen appliances, snacks, water, dishwasher soap, detachable shower heads, makeup towels, extra pillows/blankets etc. The home was warm and overall clean. There is a slight stale smell but every home has a smell. Overall we are very happy we went with this listing for our trip. It is clear the hosts care about their visitors’ stay.
Home in Saint Charles
4.81 out of 5 average rating, 36 reviewsStunning 4 bedroom, 4 bath, pool, theater, etc
We enjoyed staying at Amber's place for the week of Thanksgiving. Good location and very comfortable. Would stay again.
Home in Washington
5 out of 5 average rating, 7 reviewsMill 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.
Home in Dittmer
4.96 out of 5 average rating, 445 reviewsHoneymoon Suite Camp Skullbone In The Woods
We had a great stay here. It was extremely cozy and so bright and warm in the morning. The bed was comfortable and the surrounding nature was so peaceful. I really appreciated how it was close to a main road enough that it didn't feel remote, but was very private and tucked away.
Home in Gray Summit
4.88 out of 5 average rating, 150 reviewsSunset Mountain Privacy Retreat
Rebecca was an excellent host and even barring the Winter weather it was a beautiful landscape and view. The home was warm and cozy and clean and had many 'extras' to make sure you were comfy even if you forgot something. She isn't joking about her hilltop home with a steep drive so definitely make sure you have 4 wheel as a fair weather vehicle will most definitely be parked at the bottom of the hill but she did offer a ride if it would have been needed ❤️ The master bed was exceptionally comfortable and there were no squeaky doors or failing plumbing/electricity (always a plus when everything works 😁) We stayed with our Neapolitan Mastiff for a dog show at the local Purina Farms and she never even flinched at allowing her to stay. We will be booking her place again for the next show we attend for sure and hopefully get a different seasons view from her super cozy deck over looking miles of open landscape 🌄
Weekly house rentals
Home in Overland
5 out of 5 average rating, 3 reviewsCute and Quaint Bungalow
Loved the e place. Pictures matched exactly. I would definitely stay there again if I’m ever in town.
Home in Ballwin
5 out of 5 average rating, 22 reviewsPerfect 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!
Home in Central West End
4.95 out of 5 average rating, 152 reviews3,000 SF 4+ bdrm Private Home in Central West End
The host was absolutely wonderful, very responsive and even offered to extend our checkout when requested. Very pleased with the service. Our family truly enjoyed time in the house, visiting the arch, caves and more. I will say that the neighborhood in general is run down and a little scary. I know around downtown in St. Louis isn’t the safest area so we went into it knowing that. The oven and toaster could use updates as they were slow to heat up. Overall the stay was great and appreciate the amount of bathrooms, beds, and the playroom was perfect for my little 2 yr old daughter. They also had an ice machine which was a nice touch.
Home in Marthasville
5 out of 5 average rating, 4 reviewsHappyApples 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.
Home in St. Louis
4.83 out of 5 average rating, 190 reviewsBeautiful and Spacious 3BR Newly Renovated Home
This home is lovely! Exactly as shown in the photos, a beautiful renovation on a great, historical home. It was spotless and cozy as well as a very quiet neighborhood. Thanks for a great stay!
Home in The Hill
4.99 out of 5 average rating, 165 reviewsSpacious Bungalow on "The Hill"
We are originally from the area and were in town visiting family. This was the perfect place for my wife and I to stay. It was clean, comfortable, had the charm of The Hill and is close to some of our favorite restaurants. The holiday decorations were a nice touch. Check-in was easy and the host was very responsive and checked in to to make sure our stay was going great.
Home in The Hill
4.79 out of 5 average rating, 102 reviewsFragola House
I was in town for my daughter’s show at Webster University and stayed four nights. It quickly became a home to me and I really enjoyed my time! Great central location to everything we were doing and only about 10 min from campus. I would love to stay here again!
Home in Saint Ann
4.85 out of 5 average rating, 13 reviewsCharming quiet 2 bedroom duplex
I was extremely impressed with my stay. The area was nice, easy check in and check out process, and they check to see if I had any concerns. I would stay there again in the future should I need accommodation.
Private house rentals
Home in Florissant
4.77 out of 5 average rating, 62 reviewsMore bang! Less buck! Nice Quiet Neighborhood!
Me and my bridesmaids stay was amazing we felt right at home last weekend. I highly recommend her home we definitely will be booking again soon!
Home in Tower Grove South
4.87 out of 5 average rating, 110 reviews☆ Hot Tub ☆ New Renovated ☆ Massage Shower ☆Yard☆
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!
Home in Belleville
4.91 out of 5 average rating, 108 reviewsSpacious 2/1 w/large yard only 20 min to STL Arch
Charming little home, well-appointed and close to St. Louis and its eastern suburbs. Large lot offers privacy and room to relax and play.
Home in Saint Charles
4.96 out of 5 average rating, 80 reviewsOld Charm on Fifth 4B 2.5B/ 10 Guests 5min to Main
Absolutely loved staying at Emily’s property! Views were amazing! Lots of natural light in all rooms w/great window coverings for privacy at night. Photos definitely don’t show it just in just how spacious this property is. Very peaceful and it was perfect for our family of 8! We didn’t want to leave. Emily was great and we look forward to staying here again [when available] for we love St Charles! Thank you Emily!!
Home in St. Louis
4.84 out of 5 average rating, 19 reviewsPrivate 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!
Home in Soulard
5 out of 5 average rating, 37 reviewsThe 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!
Home in St. Louis
4.92 out of 5 average rating, 377 reviewsSunny South City Guest House
David’s place is airy, tidy, and efficient. Retro-modern furnishing and lots of plants make for a relaxing environment. It is easy to find, private, and quiet. We were there in snowy January, but I can imagine the outdoor table and carnival lights outside would be lovely in more temperate weather! We hope to stay here again when we are next in the area!
Home in St. Louis
5 out of 5 average rating, 30 reviews3325: Bright Urban Comfort by JZ Vacation Rentals
Perfect place to stay! Roomy and has everything you need.
Quick stats about house rentals in Chesterfield
Total rentals
10 properties
Total number of reviews
220 reviews
Family-friendly rentals
10 properties are a good fit for families
Wi-Fi availability
10 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool
Local attractions
St. Louis Premium Outlets, Faust Park and Chesterfield Mall
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