Pet-friendly holiday rentals in Chesterfield

Pet & Child Friendly*Great Location*Ideal 4 Groups

Stay Awhile is more than a place to stay—it’s a memory maker! This spacious St. Louis vacation rental is tucked in a fantastic neighborhood & less than 30 minutes from top St. Louis attractions-like the Zoo & Arch! Designed for families, groups & pets, it offers cozy beds, a well-stocked kitchen & plenty of space for everyone. A one-of-a-kind Eye Spy game is hidden throughout the décor, making the home part of the adventure. Perfect for those who love comfort, convenience & a touch of whimsy.

Pets · Walkability · Amenities

Pacific Palace, super unique!

The Pacific Palace is unlike any other Airbnb! Located in the heart of downtown Pacific, Missouri - only 2 minutes from Highway 44 and 10 minutes from Purina. This house is an incredible one of a kind treasure with lots of unique features including: outdoor gazebo, fish pond, all original cedar interior design, two second story balconies, two large bat tubs (one located in the main bedroom) and so much more!!! Private parking and a gate for added privacy. Just minutes from Six Flags. Book today

Walkability · Pets · Kitchen

Duplex - 1BLK from Historic DT

Admire this unique historic home's design with brand new amenities and antique details that give a fresh, peaceful, and charming feel. Built in the late 1800s, this half of the duplex is two stories. The front door leads directly to the living room, with ten-foot ceilings giving a spacious feel. The dine in kitchen is fully stocked and leads to a small closed in porch and there is a fully updated bathroom located downstairs. The second story has two relaxing bedrooms with rustic exposed brick.

Walkability · Pets · Condition

Sunset Mountain Privacy

Along Route 66, just 4 minutes from Purina Farms, this shared property is dedicated to your privacy, where you’ll enjoy a jacuzzi tub, private deck, 3 bedrooms, 2 full baths, gas fireplace, fully stocked kitchen, fenced in area for dogs, relaxing garden areas, walking trails through the woods, fire pit, and an above ground pool in the summer months. Great for weekend getaways and anyone wanting to unplug. I stay in lower level with my husband and 11 year old son (who is usually gone weekends).

Outdoor spaces · Pets · Indoor spaces

Getaway House | St Charles 4BR Sleeps 11 Game Room

DUE TO DEMAND - MUST READ: Starting August 31st, we're adding a second master ensuite - king bed, private full bath - and expanding the game room by 500 sq ft to a full 900 sq ft of pure entertainment: pool, arcade, and a big screen. We're closed September and October to build it, then reopening November 1st, completely brand new. All of our fall and winter dates are open right now, and holiday weekends at a house this size always go very quickly, so book yours before somebody else grabs them.

Pets · TV · Value

Cozy Mid-Century Modern Townhome

This comfy 2 bedroom, 1.5 bath townhome is perfect for up to 5 guests. Luxury King bed in bedroom 1 and luxury Queen bed in bedroom 2. A futon in the living room can be used for a 5th guest. A pack-n-play is available upon request. This dynamic location is 5 minutes from bars, restaurants, shopping, Lindenwood University, and Ameristar Casino. It's only 2 miles from St. Charles, historic, Main Street, and it's only 15 minutes from the airport, and about 30 minutes from downtown St. Louis.

Pets · Outdoor spaces · TV

*NEW HotTub* The Jewel on 5th-2br2b-near 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.

Outdoor spaces · Walkability · Nearby

Cottage on Main Street- Low Cleaning Fee

MESSAGE FOR SHORT STAY DISCOUNT Stay in the heart of Historic Downtown St. Charles! WALK EVERYWHERE at this beautifully updated 2BR/1BA blends modern comfort with charm just steps from Main Street. Walk to award-winning restaurants, unique boutiques, coffee shops, festivals, and riverfront views. Directly across from the Katy Trail, perfect for biking and morning strolls. Minutes to Ameristar Casino and 12 minutes to STL Airport. Fast Wi-Fi, cozy beds, and an unbeatable location.

Walkability · Pets · Check-in

The Frenchtown Inn | 2BR Charmer

Welcome to the Frenchtown Inn on the corner of Third and French! Experience the best of St. Charles in this charming 2-bedroom, 2-bathroom house situated in the heart of Frenchtown. This delightful space offers a perfect blend of comfort, convenience, and a touch of history, ideal for an unforgettable stay. We are dog friendly, complete with a fenced in yard. The Frenchtown Inn awaits you. Come experience a memorable, relaxing getaway with family or friends in our inviting home!

Walkability · Pets · Getting around

2bed/2bath Walk Main St Shops Eateries & Bars!

The "Lion House" is a completely restored charming 1930s home located in the heart of St. Charles’ National Historic District & has tons of amenities. Explore all that St. Charles has to offer…perfect place to stay (Lindenwood University - only 1 mile away) and play as you are only steps from the walkable historic Main Street lined w/boutiques, eateries, gourmet shops, Katy Trail (bike trail & rentals), pubs & nightclubs! This unique place has a style all its own.

Walkability · Pets · Laundry

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!

Walkability · Outdoor spaces · Layout

Cul De Sac - next to the best shopping in STL

Watch the snow cover the trees on this wooden landscape on a quiet cul-de-sac. Within 10 minutes to West County Mall, restaurants, great shops, corporate headquarters, tennis courts + parks, and entertainment. EASY highway access within 2 minutes, 15 minutes from downtown St. Louis. House has multiple places to entertain indoors and great hot tub, yard games, fire places and BBQ. Family friendly and enough beds for the kids and family to stay!

Outdoor spaces · Walkability · Parking