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Vacation rentals in Chesterfield

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Top-rated vacation rentals in Chesterfield

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Chalet in Wright City

5 out of 5 average rating, 11 reviews

On The Rocks by Innsbrook Vacations!

DanielRating, 5 stars3 weeks ago

Innsbrook is one of the nicest private resorts in the area. This particular stay is very accommodating for larger families or maybe two small families looking for a lake vacation. the hot tub with the TV under the deck was perfect for us! The golf course is immaculate! Dane was a great host and very responsive!

Chalet in Innsbrook

4.95 out of 5 average rating, 178 reviews

Clean & Cozy Chalet in a Relaxing Wooded Scene.

AlexandraRating, 5 stars3 weeks ago

The Missing Peace Chalet was exactly what we needed for a last minute weekend getaway. It rained a lot, which we knew beforehand and picked this Chalet so we could enjoy listening to the waterfall and enjoy being surrounded by nature during rainfall. Truly a place where you feel like you can pause the craziness of life for a moment. We will definitely be back when it’s not a rainy weekend so we can enjoy all the extras that Laura and Russell offer when staying within Innsbrook. If I could give more than 5 stars, I would.

Guesthouse in Gray Summit

5 out of 5 average rating, 5 reviews

Restoration Ranch Carriage Guest House

GaryRating, 5 stars1 month ago

Our stay at the carriage house surpassed our expectations. The grounds were so beautiful and pristine. The carriage house was so nice. The bed was so comfortable. Our dog, Ellie loved to hang out with the horses. She whined because she did not want to go in. Stephanie was such a gracious host. We will definitely return when we are in the area again.

Cottage in Innsbrook

4.88 out of 5 average rating, 100 reviews

Dock & Resort Perks: Quiet Lakefront Cottage

RRating, 5 stars4 months ago

We stayed for the Thanksgiving weekend and had a great time and even got some snow. The house is cozy and has a great view. We saw lots of wildlife from the warmth of the cabin. Would love to visit again in the warmer weather and enjoy the water sports. Everything was clean and the house was well stocked with everything you might need for a weekend in the woods.

Loft in Saint Charles

4.84 out of 5 average rating, 148 reviews

Main Street Historic Loft

DanielleRating, 5 stars1 month ago

This places was excellent. We enjoyed our stay. The place was cozy and comfortable, had what we needed. We were there on a Friday night…be warned it can get a little noisy outside so if that bothers you, then staying on a fairly busy street with lots of businesses probably isn’t for you. We weren’t bothered at all. Lots of great stores and restaurants on the same stretch of road. Definitely enjoyed our stay.

Top guest favorite

Home in Grafton

5 out of 5 average rating, 23 reviews

Stay In A Piece Of History

ElizabethRating, 5 stars1 day ago

Had a wonderful time in downtown Grafton for my daughter’s 21st birthday. The house is in a great location for walking distance to all attractions, restaurants, bars, shops and more. It was nice to not have to drive anywhere after celebrating her birthday! We will definitely be back!

Top guest favorite

Home in South Hampton

5 out of 5 average rating, 41 reviews

Blair's Amazing House Sleeps 10 - 5 Beds - 2 Bath

HowardRating, 5 stars2 weeks ago

The house is well laid out, clean, and in a nice neighborhood. The location is convenient, safe, and quiet. The owner was responsive and flexible. While there is a garage, we never used it as there was always on-street parking right in front of the house. Everyone in our party thought it was a great choice!

Vacation rentals for every style

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Popular amenities for Chesterfield vacation rentals

Free parking on premises

Air conditioning

Stay near Chesterfield's top sights

St. Louis Premium Outlets33 locals recommend

Chesterfield Outlets30 locals recommend

Topgolf27 locals recommend

Russell's Cafe & Bakery12 locals recommend

The Shack11 locals recommend

Trader Joe's11 locals recommend

Other great vacation rentals in Chesterfield

Home in St. Louis

4.89 out of 5 average rating, 207 reviews

Home away from Home St. Louis Cnty Ladue Schools

RaphaëlleRating, 5 stars3 weeks ago

Lisa was great! I needed a calm, peaceful and clean place for 2 weeks to recover from a surgery and her house was perfect. She was flexible with my arrival and departing time as I got updates from my surgeon and always worked it out with me, even last minute. There's a nice little park and neighborhood around and the house is very comfortable. Highly recommend!

Chalet in Innsbrook

4.82 out of 5 average rating, 116 reviews

Big Lake 'Livin A-Frame Chalet in Innsbrook Resort

TanyaRating, 5 stars1 month ago

My family and I used this location for spring break and we had a blast. We were able to light a fire, use the boats, and jacuzzi. The place was very clean. Any issues (which was very few) were addressed imediately. Thank you so much for allowing us the opportunity to stay at your beautiful cabin

Home in St. Louis

5 out of 5 average rating, 40 reviews

Bright Urban Comfort by JZ Vacation Rentals

AmandaRating, 5 stars1 day ago

This house was perfect for a larger group! We felt like we had a lot of space even with 12 people in the house! The location was perfect, as it only took 7-9 minutes to get to most tourist attractions. We appreciated how clean the house was as well! The house is exactly as it shows in the pictures! We would definitely stay here again on our next trip!

Top guest favorite

Condo in Grafton

4.98 out of 5 average rating, 166 reviews

Pelican's Perch

NickRating, 5 stars3 weeks ago

Fantastic host. Beautiful property.

Home in O'Fallon

5 out of 5 average rating, 10 reviews

Quaint and Cozy Hamlet

SavannaRating, 5 stars3 weeks ago

My cousin was getting married and we needed a place to get ready. This house was PERFECT! Kevin was so incredibly nice letting us check in early and check out late to accommodate our wedding party. He went out of his way to make sure everything was exactly how we needed it. You don’t come by many people like that anymore! So blessed and thankful for Kevin and his generosity. Will definitely stay at this house again if I’m in the area!

Condo in Grafton

4.76 out of 5 average rating, 54 reviews

One bedroom condo with great riverview.

ColinRating, 5 stars1 day ago

Great place. Great location. Daniel was super nice. Happened to be visiting on a weekend when the flea market was in session! Fun people and watching and fun visiting the flea market. Opposite end of town from the activities of the more active bars, but absolutely walkable and quiet when you wanted to get away from it all.

Chalet in Innsbrook

5 out of 5 average rating, 3 reviews

Waterside Cottage w/ Hot Tub by StayLage

BenRating, 5 stars8 months ago

Beautiful little cabin set back in a very private setting. Made for a perfect end of summer getaway

Home in Grafton

4.98 out of 5 average rating, 93 reviews

Cozy Cottage off Main Street in Grafton

LeoRating, 5 stars1 month ago

The cottage was perfect for our weekend getaway! Linda was responsive, kind, and helpful. The space was clean and cozy. Highly recommend if you want a cute space close to the fun shops and restaurants in Grafton!

Quick stats about vacation rentals in Chesterfield

Total rentals
40 properties
Total number of reviews
400 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi

Frequently Asked Questions

Are there pet-friendly vacation rentals in Chesterfield?
Four-legged friends are welcome in Chesterfield. Choose from more than 20 vacation rentals for guests traveling with pets.
How much does it cost to stay in apartment rentals in Chesterfield?
Experience the best of Chesterfield with our apartment rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly vacation rentals in Chesterfield?
Chesterfield has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there vacation rentals with a dedicated workspace in Chesterfield?
Yes! Work meets play with ease at over 20 vacation rentals in Chesterfield featuring dedicated workspaces. Stay connected and productive in your home away from home.

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