Holiday rentals in Chesterfield

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Top-rated holiday rentals in Chesterfield

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Top guest favourite
The charming front porch features a white wicker chair and a decorative wreath, inviting relaxation. Greenery surrounds the entryway, complemented by a well-maintained lawn. A gravel pathway leads from the porch to the driveway, creating a welcoming entrance to the guest house.
Home in Saint Charles
4.97 out of 5 average rating, 713 reviews

301 Guesthouse- Historic Main street-Katy Trail

Our 301 Guest House is new and completely remodeled in 2018! It’s ideal for one or two people with beautiful furnishings, great queen bed, lots of amenities, full kitchen, with big back yard and patio to enjoy outdoors too! Cable and FAST WiFi! Enjoy light Breakfast! BEST location, Great events year round within walking distance, with being only about 2 blocks from S. Main St, where there are about 100 gift shops n restaurants! Katy Trail is so close, with Spring, Summer, Fall and Xmas events!

Top guest favourite
A log cabin with a dark metal roof is featured, accompanied by a covered porch area containing two chairs. Surrounding landscaping includes a well-maintained lawn and decorative stones, providing a natural setting that complements the cabin's rustic design.
Cabin in Pacific
4.99 out of 5 average rating, 134 reviews

Catch The Dream:; An Immersive Equestrian Escape

Welcome to the most serene and immersive equine retreat in the area! We are so happy you decided to stay with us. We want you to feel relaxed and at home as you enjoy the equine activities as well as the cozy log cabin and all its features and amenities! Enjoy views of the lush property and relax as you watch the horses graze and roam. We offer customized horsemanship opportunities that accommodate each person's level of comfort and ability. Cost: $75 for two hours, maximum of two lessons/day

Top guest favourite
The exterior of a historic log cabin features a welcoming yellow door and a decorated porch with a small table and chairs. Lush greenery surrounds the cabin, while vibrant flowers add a touch of color. The structure is complemented by the clear blue sky.
Cabin in Saint Charles
4.98 out of 5 average rating, 371 reviews

Camp Mill Pond: Historic Cabin Near Main Street

*St. Louis Magazine A-List Winner!* ***PRESS: DESIGN STL, STL MAG, AND FOX2NEWS*** Camp Mill Pond is a throwback to the slow and easy rhythm of hot summer days. This circa 1835 cabin offers easy access to our historic area, including Main Street, Katy Trail for biking, and Frenchtown, without sacrificing modern comforts! This 180-year-old historic cabin sits on a beautiful lot, shared with our 1865 three-story home and a two-story carriage house. Ask about renting bikes and a golf cart!

Top guest favourite
A cozy living room is highlighted by a vintage-style mirror and decorative fireplace. Comfortable seating, including a golden armchair, is arranged around a central coffee table. Large windows allow natural light to flow in, complemented by patterned curtains and a detailed area rug.
Flat in Southwest Garden
4.94 out of 5 average rating, 360 reviews

Historic Victorian comfort Great safe nghbhd

First, check out all 4 of our private 5 Star listings that creatively combines the old with the new. If one is unavailable, check the others by going to “My Profile” and scrolling down until you see all 4. This Historic building; built in 1896 has changed missions through the years; From church, to merc. Trade, to grocery store; quite the history have graced these walls. You’ll love our safe, Southwest Gardens area; next to the famous “Hill” offers unmatched restaurant, shops, bakeries

Top guest favourite
A private hot tub is illuminated with soft blue lights, surrounded by a wooden fence. String lights hang overhead, enhancing the evening ambiance. The area offers seating options, creating a cozy space for relaxation.
Cottage in Augusta
4.89 out of 5 average rating, 111 reviews

Romantic Augusta Cottage-Relax & get away!

This cottage is designed to strengthen and refresh couples looking for a getaway from busy life. Relax in the comfortable Living room or prepare a meal in the recently updated fully furnished kitchen. Enjoy your nights in the spacious bedroom furnished with a California King sized bed and TV in the room. Enjoy the private hot tub just steps from the door or use the BBQ pit to create a meal to enjoy together. Area restaurants, wineries & golf are just minutes away! You are sure to enjoy!

Guest favourite
A small dining area features a square table surrounded by four black stools. A potted flower adds a touch of color to the table. Modern flooring in shades of gray highlights the space, leading toward a kitchen area in the background.
Guest house in St. Louis
4.9 out of 5 average rating, 110 reviews

The Blue Door in Creve Coeur

Perfect location for quick access to everything StL. Come home to a peaceful and spacious smokefree property. Sit on the patio and watch deer and squirrels running around. The main area is large and open concept. Bedrooms are big and comfortable, with their own fireplace heater. There is plenty of closet room. Laundry room included with a folding table and an iron. Spacious bathroom with a large shower with a seat! The Walkway to the frontdoor is down a small incline. please see pictures.

Superhost
A grey sectional sofa is positioned next to a circular glass table, creating a comfortable seating area. Natural light floods the space through large glass doors leading to the outside. A potted plant adds greenery, while wall decor spells out 'HOME.'
Home in St. Louis
4.91 out of 5 average rating, 126 reviews

St. Louis Home away from Home!

Our property is the perfect place for anyone looking for a peaceful stay in STL! This 4BR, 2.5 BA house gets amazing natural light throughout the day, and is nearly too cozy! Located 12 minutes from the airport, and near many of STL’s top attractions, our home is sure to leave you feeling refreshed after your stay! We’re a family that is dedicated to ensuring our guests enjoy the best experience possible. As local hosts, you can rest peacefully knowing that we are just a phone call away!

Superhost
The modern home features a spacious wooden deck with steps leading to a well-maintained garden. Large glass doors dominate the front facade, allowing natural light to flood the interior. Lush trees provide a serene backdrop, complementing the inviting outdoor space.
Home in Fairview Heights
4.88 out of 5 average rating, 120 reviews

Wooded Oasis with Free Bottle of wine+brkfst

Enjoy serenity and tranquility at our modern home tucked away in a private setting just 5 short minutes from Downtown St Louis. Complementary bottled water, continental breakfast(packaged muffins) and a bottle wine will pamper you the moment you arrive.Unwind in our luxurious multifunction shower+memory foam mattress Test your swing on our scenic driving mat or unwind around the crackling outdoor fire pit. Spa and Special Occassion add-on packages available. Private off street parking.

Guest favourite
A cozy living room features a large gray sectional sofa, complemented by two wooden chairs. Natural light enters through sheer window coverings, illuminating the space. A light-colored rug adds texture underfoot while artwork decorates the walls, enhancing the room's comfortable atmosphere.
Home in Saint Charles
4.85 out of 5 average rating, 160 reviews

Family/4bd/2bth/Huge Yard/Playset/Ping-Pong/Arcade

Our freshly updated and furnished house is ready for the family with kids, the adult getaway, and wedding parties from Stone House event venue across the street! Boasting tons of privacy, a huge yard with a playset and games, a fully stocked kitchen with everything you could want for a Thanksgiving dinner, and a large basement with arcade boxes, ping pong, weights, and seating areas. A very safe and secluded location that is close to amazing parks, restaurants, wineries, and shopping.

Top guest favourite
The exterior of a chalet is illuminated at night by warm string lights. Large windows reflect soft interior light, revealing a cozy atmosphere. The wooden deck is accessed by a railing, creating a welcoming entry. Trees are visible in the background, adding natural charm.
Home in Dittmer
4.96 out of 5 average rating, 587 reviews

Honeymoon Suite at Camp Skullbone In The Woods

Experience a romantic, quiet, and cozy chalet designed for two! This charming retreat features vintage décor and all the modern amenities you need for a comfortable stay. Unwind indoors by kicking back and watching a movie, surfing the web, curling up with a good book or a friendly board game, or sharing a drink with that special someone. In the evening, relax on the cozy deck under the stars, basking in the warm glow of the gas fire pit or unwinding in the inviting private hot tub!

Top guest favourite
Home in Rock Hill
4.95 out of 5 average rating, 177 reviews

Family Friendly Cozy Home w/ Lrg Fenced Yard

**FAMILY FRIENDLY** (See details for the items avail for families) This 2 bedroom home has everything you need for a relaxing trip! Fully updated with stylish and comfortable furniture and decor. Fully equipped kitchen and an amazing backyard/deck. Quiet street by one of the best Mexican restaurants in St. Louis - Hacienda - (can walk 2 min there) Close to everything! 13 minutes to the St. Louis Zoo 10 minutes to The Magic House 15 minutes to Busch Stadium & Union Station

Top guest favourite
The exterior of the house features a well-maintained lawn with shrubbery and a covered porch. A cozy seating area with a modern coffee table is shown, complemented by a sectional sofa. A well-equipped kitchen with appliances and a dining table set for six are also visible. A serene bedroom showcases a spacious bed with soft linens.
Home in Saint Charles
4.99 out of 5 average rating, 199 reviews

Little House By Main St -5 4K TV's- 1-75 Inch -1GB

Little House By Main St -5 4K TV's- 1-75 Inch -1GB Internet- No location has better access to so much. All the best amenities on both sides of Main Street St Charles! Walking distance from the Ameristar Casino, Texas Road House, Main Street (Honky Tonk, Big A's, Q, Thirstys), Starbucks, Taco Bell, Buffalo Wild Wings, McDonald's and the Bars / Restaurants on Main. An Awesome Location for all of the Festivals in St Charles! And secured parking in the 1 car garage!

Popular amenities for Chesterfield holiday rentals

Frequently Asked Questions

  • 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.

  • How much does it cost to stay in apartment rentals in Chesterfield?

    Experience the best of Chesterfield with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • 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.

  • 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.

  • Are there Chesterfield vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Chesterfield, available on Airbnb. Make a splash and soak up the sun in style!

  • Where should I stay in Chesterfield?

    Make yourself at home in Chesterfield by choosing from our most frequently booked neighborhoods. We have over 40 vacation rentals in Brook Hill Estates, and over 40 vacation rentals in Meadowbrook Country Club Estates.

  • Do apartment rentals in Chesterfield have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning in Chesterfield. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Chesterfield have a kitchen?

    Absolutely! We offer over 10 apartment rentals with a kitchen in Chesterfield. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Chesterfield have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Chesterfield. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Chesterfield have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Chesterfield. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Chesterfield

  • Total holiday rentals

    Explore 40 holiday rentals in Chesterfield

  • Nightly prices starting at

    Chesterfield holiday rentals start at € 26 per night before taxes and fees

  • Verified guest reviews

    Over 320 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 of Chesterfield holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chesterfield rentals

  • 4.6 Average rating

    Chesterfield stays receive an average rating of 4.6 out of 5 from guests