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, 126 reviews

Private indoor pool & sauna

PamRating, 5 stars2 months 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.
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 stars7 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, 153 reviews

Clark Brick House w/ Pool | Historic St. Charles

BrianRating, 5 stars1 month 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 favourite

Home in Creve Coeur

4.96 out of 5 average rating, 51 reviews

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

ElianaRating, 5 stars1 month ago
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.
Superhost

Home in Saint Charles

4.81 out of 5 average rating, 36 reviews

Stunning 4 bedroom, 4 bath, pool, theater, etc

MichaelRating, 5 stars2 months ago
We enjoyed staying at Amber's place for the week of Thanksgiving. Good location and very comfortable. Would stay again.
Superhost

Home in Washington

5 out of 5 average rating, 7 reviews

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

KristinaRating, 5 stars5 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

4.96 out of 5 average rating, 445 reviews

Honeymoon Suite Camp Skullbone In The Woods

JustynRating, 5 stars2 weeks ago
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.
Guest favourite

Home in Gray Summit

4.88 out of 5 average rating, 150 reviews

Sunset Mountain Privacy Retreat

Jesse EscajedaRating, 5 stars1 week ago
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

Superhost

Home in Overland

5 out of 5 average rating, 3 reviews

Cute and Quaint Bungalow

AlexRating, 5 stars4 months ago
Loved the e place. Pictures matched exactly. I would definitely stay there again if I’m ever in town.
Guest favourite

Home in Ballwin

5 out of 5 average rating, 22 reviews

Perfect Getaway 3BR/3BA Home

LaurieRating, 5 stars5 days 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!
Superhost

Home in Central West End

4.95 out of 5 average rating, 152 reviews

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

KristinRating, 5 stars1 month ago
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.
Superhost

Home in Marthasville

5 out of 5 average rating, 4 reviews

HappyApples BicycleBunkhouse-WholeHouse-Sleeps 23

EmilyRating, 5 stars7 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, 190 reviews

Beautiful and Spacious 3BR Newly Renovated Home

AmyRating, 5 stars1 month ago
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!
Guest favourite

Home in The Hill

4.99 out of 5 average rating, 165 reviews

Spacious Bungalow on "The Hill"

JohnRating, 5 stars1 month ago
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.
Guest favourite

Home in The Hill

4.79 out of 5 average rating, 102 reviews

Fragola House

HilaryRating, 5 stars1 month ago
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!
Superhost

Home in Saint Ann

4.85 out of 5 average rating, 13 reviews

Charming quiet 2 bedroom duplex

Charlotta ReginaRating, 5 stars1 week ago
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

Superhost

Home in Florissant

4.77 out of 5 average rating, 62 reviews

More bang! Less buck! Nice Quiet Neighborhood!

TRating, 5 stars3 months ago
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!
Superhost

Home in Tower Grove South

4.87 out of 5 average rating, 110 reviews

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

DillonRating, 5 stars3 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 favourite

Home in Belleville

4.91 out of 5 average rating, 108 reviews

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

C. MichaelRating, 5 stars2 months ago
Charming little home, well-appointed and close to St. Louis and its eastern suburbs. Large lot offers privacy and room to relax and play.
Guest favourite

Home in Saint Charles

4.96 out of 5 average rating, 80 reviews

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

TracyRating, 5 stars2 weeks ago
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!!
Superhost

Home in St. Louis

4.84 out of 5 average rating, 19 reviews

Private 2 Bedroom 1 Bath House

JuliaRating, 5 stars1 month 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 Soulard

5 out of 5 average rating, 37 reviews

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

KaylaRating, 5 stars1 week 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

4.92 out of 5 average rating, 377 reviews

Sunny South City Guest House

AnnieRating, 5 stars2 weeks ago
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!
Guest favourite

Home in St. Louis

5 out of 5 average rating, 30 reviews

3325: Bright Urban Comfort by JZ Vacation Rentals

KendraRating, 5 stars1 month ago
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

Destinations to explore