Chesterfield Holiday Rentals from €101: Search Short-Term Rentals

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Our top choices for Chesterfield holiday rentals

A spacious living area with a high ceiling, wooden beams, a fireplace, a dining area, and a cozy seating arrangement.

1. Private 3-Acre Retreat • Koi Pond & Waterfall

Wildwood

"Our host was incredibly accommodating and went above and beyond to make sure we had everything we needed throughout our stay. The property was beautiful, exceptionally clean, and offered the perfect amount of privacy.We truly can't say enough about how much we enjoyed our stay. It exceeded our expectations in every way. Whenever we return to St. Louis, this will absolutely be our first choice. We look forward to staying here again!"

Robin H.

includes taxes & fees

23 Nov - 24 Nov

A set of stone steps leading to a garage with a car parked inside.

2. Studio, sleeps 5, short drive to Hidden Valley Ski Resort, parks &concert venues

Ballwin

Keith K.

A hotel lobby with a staircase, a reception desk, and a seating area.

3. 2 Queen Beds | Mobil Access Tub Nsmk Kitchen

Westport

Anonymous traveller

A residential building with a patio area featuring outdoor furniture and string lights.

4. Private Entry Basement Suite • Pond & Farm View • Dog Friendly • St Peters

St. Peters

Lynn D.

includes taxes & fees

10 Nov - 11 Nov

A spacious living room with hardwood floors, a white armchair, a dark sofa, and a television on a stand.

5. Casa de Saint Charles

Saint Charles

Xavier H.

An outdoor hot tub area with seating and a covered patio.

6. Private Basement - Two King Beds and Hot Tub

Saint Charles

Beth S.

includes taxes & fees

8 Nov - 9 Nov

A neatly made bed with a stack of folded towels, a bedside lamp, and a ceiling fan in a room with a large window and a wall-mounted artwork.

7. Home Near Main with Pet-Friendly Yard and Office

St. Charles Historic District

Jessica S.

A row of multi-story buildings with commercial storefronts, including a cafe and a restaurant.

8. Dog-Friendly Studio on Historic Main Street

St. Charles Historic District

Sarah C.

includes taxes & fees

9 Nov - 10 Nov

A spacious living room with a green sofa, a purple armchair, a wooden staircase, and a ceiling fan.

9. St. Charles 1860's Gem - Sleeps 6!

St. Charles Historic District

Jackie D.

includes taxes & fees

8 Nov - 9 Nov

A hotel room with a bed, a desk, a chair, a lamp, and a telephone.

10. 1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

Westport

Anonymous traveller

includes taxes & fees

10 Nov - 11 Nov

A modern kitchen with stainless steel appliances, white cabinetry, and a brick accent wall.

11. Historic Main St. Customs House Upstairs Apartment

St. Charles Historic District

Margaret A.

includes taxes & fees

9 Nov - 10 Nov

A bedroom with a bed, bedside table, and a large painting on the wall.

12. 6649 1E | Garden Style Studio Near Forest Park

Dogtown

Dhgirlie H.

includes taxes & fees

30 Nov - 1 Dec

A living room with a sofa, armchairs, a coffee table, a lamp, a ceiling fan, and a rug.

13. Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!

St. Charles Historic District

Jeffrey E.

A spacious kitchen with white cabinets, a central island with bar stools, a stainless steel refrigerator, and a microwave.

14. Spacious, 3 bedroom home, finished basement on quiet court

St. Peters

ed n.

includes taxes & fees

8 Nov - 9 Nov

A cozy living room with a brick wall, a white sofa with colorful cushions, a small black table, and a potted plant.

15. Prime Loft of Main Street

St. Charles Historic District

Richard W.

includes taxes & fees

8 Nov - 9 Nov

A spacious foyer with a grand staircase, a piano, and a large rug.

16. White House at Grand Central

Grand Center

Priscilla

includes taxes & fees

8 Nov - 9 Nov

A modern kitchen with white cabinets, a black refrigerator, and a central island.

17. Cottage on Main st- Low Cleaning Fee

St. Charles Historic District

Debbie A.

A spacious living area with a wooden floor, a dining table with chairs, a flat-screen TV mounted on the wall, and a kitchen area with modern appliances.

18. The Lofts of North Main Street

St. Charles Historic District

Liberty A.

includes taxes & fees

9 Nov - 10 Nov

A living room with a white sofa, a black sofa, a glass coffee table, and a cityscape painting.

19. 6653 2S | Jewel of Central St. Louis

Dogtown

Ashley C.

includes taxes & fees

16 Nov - 17 Nov

20. Charming 2-bedroom house in nice Imperial with AC. Attn! Traveling Contractors

Imperial

Tommy H.

includes taxes & fees

6 Nov - 7 Nov

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Top Chesterfield Hotel Reviews

Clayton Plaza Hotel & Extended Stay

10/10 Excellent

"Gteat hotel, very friendly and helpful staff. Continental breakfast was excellent, easy access to parking. Everything was great."

Find out more about Chesterfield

Everything you need to know about Chesterfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterfield holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesterfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterfield holiday rentals we have selected for you start as low as €101 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chesterfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterfield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find holiday rentals in Chesterfield?

Yes, there are holiday rentals in Chesterfield close to Sophia M. Sachs Butterfly House, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Chesterfield. Make sure you have time to check out the sporting events and museums during your trip.

What are some of the best holiday rentals that Chesterfield has to offer?

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!: This holiday home rental outside of Chesterfield is located in the city centre, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Chesterfield?

Choose from 8 Expedia holiday rentals in Chesterfield for a memorable holiday.

What can I see and do in Chesterfield?

Family-friendly attractions include Sky Zone Indoor Trampoline Park - St. Louis and Myseum, whereas Missouri River and Sophia M. Sachs Butterfly House are a couple of great spots to enjoy the outdoors. Other places in town to visit include The Factory and St. Louis Premium Outlets.

What are holiday rentals like in Chesterfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesterfield. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a family getaway.

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Check prices for these dates

Our top choices for Chesterfield holiday rentals

1. Private 3-Acre Retreat • Koi Pond & Waterfall

2. Studio, sleeps 5, short drive to Hidden Valley Ski Resort, parks &concert venues

3. 2 Queen Beds | Mobil Access Tub Nsmk Kitchen