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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 stars2 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 stars2 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.

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, 22 reviews

Stay In A Piece Of History

KimRating, 5 stars3 weeks ago

Caroline's place is amazing. The location is perfect. It is right on the main street and walkable to restaurants and shops. Seven of us stayed there for a girl's weekend, and we had plenty of space. We enjoyed the outdoor seating as well as the enclosed front porch area with the hanging swing.

Top guest favorite

Home in South Hampton

5 out of 5 average rating, 40 reviews

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

JordanRating, 5 stars2 weeks ago

Matt’s listing was convenient driving to all that St Louis has to offer and walkable to several local restaurants, coffee, and park with brewery. We enjoyed the location very much. The house was as described and fit our needs for two families of 4 to stay. We enjoyed our stay.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

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

Top guest favorite

Vacation home in Washington

4.97 out of 5 average rating, 34 reviews

Pool + Hot Tub, Downtown, Wineries, Spacious, Cozy

KimRating, 5 stars1 month ago

My friends and I have been coming to the Brick House for years for a girls weekend. We love the location and the house has all our needs. The owners are very easy to work with and accommodating. We will be back.

Top guest favorite

Home in Innsbrook

5 out of 5 average rating, 33 reviews

Beautiful Luxury Home on water

KatyRating, 5 stars2 months ago

We thoroughly enjoyed this space! The home felt very clean and comfortable. It offers several social spaces that are very welcoming and spacious. The bedrooms are also spaced well offering privacy for all of the guests. The bathrooms are beautiful with top of the line amenities. The kitchen also has everything you could need! The home is very well supplied with all the necessities too! We would love to come back!

Top guest favorite

Home in Ballwin

5 out of 5 average rating, 29 reviews

Perfect Getaway 3BR/3BA Home

JohnRating, 5 stars1 week ago

Another perfect stay at Perfect Getaway. The home was very clean and the host communication was quick and easy. Great neighborhood and great location. I 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 O'Fallon

5 out of 5 average rating, 10 reviews

Quaint and Cozy Hamlet

SavannaRating, 5 stars2 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

4.75 out of 5 average rating, 52 reviews

One bedroom condo with great riverview.

BenjaminRating, 5 stars3 weeks ago

This place was amazing! Very comfortable, great view of the river and within walking distance of shops and great restaurants and bars. 20/10, would highly recommend.

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

Top guest favorite

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 hotel rentals in Chesterfield?
Experience the best of Chesterfield with our hotel rentals, starting at about $180 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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