Holiday rentals in Chesterfield

4.95 out of 5 average rating, 297 reviews

A spacious sleeping area features a large bed adorned with plush white pillows. Shelves display vintage cameras and decorative items, while ambient lighting is created by lamps on side tables. The walls are painted a soft blue, adding to the room's calm ambiance.

Tiny home in Pacific

Route 66 Railroad Shanty, a cozy artsy small space

This 536 s.f. house, believed to have once been a sleeping shanty for railroad crews switching shifts for the night. Fully renovated and updated in 2021 by a local artist, you will find custom metal art throughout, granite countertops and a very warm cabin feel featuring a kitchen and bathroom finished with locally sourced Missouri dark red cedar, 10 minutes from six flags, Purina farms 15 min from hidden valley and 45 min from downtown this place is in a great location and will not disappoint!

4.9 out of 5 average rating, 441 reviews

A well-lit guest room features tall vaulted ceilings with exposed wooden beams and skylights. A cozy bed is adorned with patterned bedding, while decorative plants are placed around the space. Large windows allow natural light to fill the room, complemented by soft curtains.

Home in Bevo Mill

Sunny South City Guest House

Newly-rehabbed & cozy guest house. Everything you need is located here in the historic Bevo Mill neighborhood. In the heart of south St. Louis city, you’re steps away from local businesses, including the picturesque, historical Das Bevo. Step into a vintage-styled oasis, featuring large windows with plenty of natural light, tall vaulted ceilings, comfy queen bed, unique fridge, breakfast bar, sizable bathroom with a large walk-in shower. Hang outside at the picnic table under cute string lights.

Guest suite in Saint Charles

A rustic living area features a large stone fireplace with a cozy fire and a wall-mounted television displaying a program. Comfortable seating includes a grey sofa and a round table for dining. Decorative items add character to the room.

4.93 out of 5 average rating, 110 reviews

The Luxury Lodge in St. Charles

The Luxury Lodge is a Private Residence at Rear of Property with Private Keypad Door Entrance, Private Parking, Outdoor Deck, Dog Run Line and 1/2 acre Fenced Backyard. Kick back & relax in this serene, spotlessly clean, stylish luxury & country living in St. Charles, MO w/ Great Scenic View. Dog friendly, comfy Queen Size Bed, Love Seat, Queen Sleeper Sofa, Large Stone Fireplace, Huge Bathroom, Rain Shower, Private Powder Room, Large Screen TV, Cable & Streaming, Kitchenette, Fridge & Dresser.

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.

4.97 out of 5 average rating, 664 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!

4.99 out of 5 average rating, 114 reviews

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

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

4.98 out of 5 average rating, 360 reviews

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

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!

Flat in St. Charles Historic District

A modern kitchen area features white cabinetry and a kitchen island with three cushioned stools. Pendant lights hang above the island, illuminating the space. A doorway leads to another room, with a glimpse of additional kitchen appliances visible in the background.

4.95 out of 5 average rating, 382 reviews

Christmas Getaway in Historic Old St. Charles

Welcome to Pop Luck's Guest Suite! This adorable gem represents everything you love about Old St. Charles. This cozy suite is just steps away from the heart of Main Street, restaurants, and all the action St. Charles has to offer. Pop Luck's is a charming one-bedroom, with an open and airy living room and kitchen. It has natural light and high ceilings throughout. It's farmhouse cottage decor makes for a relaxing place to rest. Also, check out our sister suite The Ella Rose, right next door.

4.94 out of 5 average rating, 160 reviews

A cozy studio layout features a spacious queen bed adorned with floral bedding. A round dining table with four chairs is positioned nearby, surrounded by warm hardwood flooring. Natural light enters through a window, enhancing the inviting atmosphere.

Home in Villa Ridge

Serenity Valley (No Cleaning Fee- No pets please)

Discover Serenity in this 675 sq ft Studio cottage on a private wooded lot. Cozy space with 1 queen bed & optional inflatable queen bed for up to 4 guests. Relax on the patio, enjoy a bubble bath in the vintage clawfoot tub, or take in the panoramic woods view on the couch. Amenities include WIFI, washer/dryer, fully stocked kitchen, DishNetwork, pack&play. Just 60 mins from downtown STL, 15 mins from Washington, 20 minutes from Six Flags. Your tranquil escape awaits! No pets allowed.

The exterior of a charming century home showcases a covered front porch with white railings and a welcoming entrance. Lush greenery and flower beds line the stone steps leading to the porch, enhancing the inviting character of the property.

4.96 out of 5 average rating, 358 reviews

*HotTub* The Jewel on 5th-2br2b-near Historic Main

A true gem only a 15 min drive from the STL Airport. Enjoy a well equipped, century home a short 12 min walk to Historic Main and a HOTTUB. The large stocked kitchen is great for entertaining. Master bedroom w/luxurious, king sized, 4 poster bed and ensuite bathroom awaits you. In the private, queen suite you’ll find its own bathroom and another door leading onto the deck. The chair off the kitchen folds out to a standard twin and bedding is provided for the sofa as well. Can sleep 6.

4.95 out of 5 average rating, 180 reviews

Two floral-patterned chairs are positioned beside a brick fireplace. A decorative wooden mantle displays various items, including a sign with the word 'LOVE.' A small table with a lamp and a patterned rug add warmth to the space.

Home in Ballwin

Entire lower level of our home w/Paris Theme

Our home is located in a quiet West St. Louis County neighborhood. The lower/walkout of this place is your home away from home. It has a private entrance from a walk around sidewalk to the backyard. You will have the entire lower level of our home. We live in the upstairs or first floor of this home. Our place is best suited for one couple, solo adventurers, business travelers, and one family (with kids). This space has been recently remodeled with a French Parisian theme!

Apartment in Saint Charles

A charming exterior view of the Rue Royale Condominiums features a covered entrance with black railings and outdoor seating. Potted plants add greenery to the space. An American flag is displayed beside the entrance, and a lamppost is visible, providing a welcoming ambiance.

4.94 out of 5 average rating, 164 reviews

Cozy Studio in Beautiful New Town St. Charles

Stay at this cozy studio centrally located in the amazing community of New Town St. Charles. New Town is a large scale new urbanist community built on the edge of suburbia. You never have to leave New Town with its walkability to restaurants, bars, a market, coffee shops, ice cream, food kiosk, canals, lakes, parks and tree lined streets. If you do leave its only a few miles from historic St. Charles Main street, The Streets of St. Charles, and 25 miles to Downtown St. Louis.

Superhost

A single-story home is depicted with a metal roof and a front door featuring a decorative window. Brightly colored flower pots filled with blooms are arranged along the path, complemented by landscaped greenery surrounding the property.

Tiny home in Pacific

4.9 out of 5 average rating, 675 reviews

Route 66 Cozy Cottage

* Fast Wifi (Spectrum) * Keypad entry (no keys to keep track of) * Private driveway by the front door for easy access to carry luggage in and out * Huge yard for dogs, kids or even adults to play * Lovely outdoor patio with plenty of comfortable seating and beautiful landscaping * For the kiddos- toys, books, and games (puzzles and games for adults too) * Essentials for your furbabies as well - treats, leashes, food & water bowls, waste bags, towels

Popular amenities for Chesterfield holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Chesterfield

The exterior of a brick building featuring a symmetrical layout, with multiple entrances spaced evenly along a concrete walkway. Lush greenery borders the pathway, and clear blue skies provide a bright backdrop, enhancing the well-maintained appearance of the property.

Serviced apartment in Lindenwood Park

4.76 out of 5 average rating, 134 reviews

Lovely 1-Bedroom apartment with free parking

The modern kitchen features sleek white cabinetry and stainless steel appliances. A central island with seating for three is complemented by a light granite countertop. Natural light streams in from a window, illuminating the space and creating an inviting work area for meal preparation.

4.91 out of 5 average rating, 66 reviews

Blair's House in St. Charles - 4 bedroom 2.5 Bath

Home in St. Charles Historic District

A cozy bathroom features a freestanding tub positioned near large windows, allowing natural light to illuminate the space. Rustic wooden beams create a warm ceiling overhead, while stone walls add textural contrast. A wooden stool holds decorative jars and a soft towel, enhancing the serene atmosphere.

4.95 out of 5 average rating, 20 reviews

Luxurious, spa-like retreat steps from Main St.

Guest suite in Weldon Spring

A queen-sized bed is featured with a patterned grey bedspread, positioned near a window with wooden blinds. A cozy chair sits in the corner, accompanied by decorative elements, including a globe and a travel-themed sign, enhancing the room's inviting atmosphere.

4.94 out of 5 average rating, 66 reviews

Wanderlust

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.

4.83 out of 5 average rating, 137 reviews

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

5 out of 5 average rating, 48 reviews

Home in Wildwood

3+ private acres, Koi fish pond, garage parking

4.87 out of 5 average rating, 76 reviews

A spacious sleeping area features a king size bed with a textured white coverlet. Soft black cushions add contrast. A full-length mirror reflects light, while an air conditioning unit is mounted on the wall. Minimalist shelving and a dark seating area are positioned along the far wall.

Loft in Saint Charles

City Loft in Saint Charles