Top 10 Hotels in Winchester, MO (from $91) 2026 - Competitive Prices

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Our top choices for Winchester hotels

A modern hotel lobby with a high ceiling, a central seating area with sofas and a coffee table, and a flat-screen TV mounted on the wall.

A modern hotel breakfast area with a central island, buffet setup, and a large window providing a view.

A spacious lobby with a high ceiling, a flat-screen TV mounted on the wall, and a seating area with sofas and ottomans.

A hotel room with a bed, a desk with a computer, a television, a sofa, and a window with a view.

1. Drury Inn & Suites Southwest St. Louis

Valley Park

Randy

$115 nightly

$135 total

Oct 7 - Oct 8

Total with taxes and fees

A modern kitchen with a bar area, wooden cabinets, and pendant lighting.

A hotel room with three computer workstations, each with a monitor, keyboard, and a lamp.

A swimming pool with a tiled deck, a sunlit room with a view, and a seating area with chairs.

A modern hotel entrance with a glass canopy, large windows, and a brick facade.

2. Hyatt Place St. Louis/Chesterfield

Chesterfield

Chelsea

$130 nightly

$150 total

Oct 5 - Oct 6

Total with taxes and fees

A spacious lobby with a central round table, two sofas, and a chandelier.

A hotel room with two beds, a patterned wall, and a view of the city through sheer curtains.

A Drury Plaza hotel with a modern design, featuring a curved facade, large windows, and a Drury Plaza sign on the top.

An indoor swimming pool area with clear signage indicating a depth of 3 feet and a no diving warning.

3. Drury Plaza Hotel St. Louis Chesterfield

Chesterfield

Cassandra

$130 nightly

$151 total

Oct 8 - Oct 9

Total with taxes and fees

A modern dining area with multiple tables and chairs, recessed ceiling lights, and a kitchen in the background.

An indoor swimming pool with tiled flooring, a pool ladder, and lounge chairs.

A gym with treadmills, elliptical machines, and a mirrored wall.

A hotel room with two beds, a desk, and a window with a view of trees.

4. Best Western Plus Fenton

Fenton

Brian

$97 nightly

$112 total

Oct 4 - Oct 5

Total with taxes and fees

A hotel with a prominent tower, a fountain in the courtyard, and a well-maintained garden.

A modern bathroom with a large mirror, white vanity, and a bathtub.

A spacious living area with a staircase, a large painting, and a chandelier.

A hotel room with a large bed, a bedside lamp, a telephone, a mirror, and a bathroom with a sink and towel rack.

5. The Wildwood Hotel

Wildwood

Cristal

$92 nightly

$107 total

Nov 2 - Nov 3

Total with taxes and fees

A modern interior with hanging pendant lights, large windows, and a view of the outside.

A modern hotel lobby with a high ceiling, multiple hanging pendant lights, a reception desk with a Missouri US 66 sign, and large windows allowing natural light.

A hotel indoor pool area with a hot tub, seating, and a view of the outdoors.

A modern hotel with a covered entrance, brick facade, and a parking area.

6. Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

Fenton

Dashaun

$89 nightly

$103 total

Nov 1 - Nov 2

Total with taxes and fees

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

A building entrance with a black door, two potted trees, and a welcome sign.

An indoor swimming pool with a tiled floor, a pool ladder, and a few chairs and tables around the pool area.

A hotel room with a large bed, a separate bathroom with a bathtub, a flat-screen TV, and a framed picture on the wall.

7. Holiday Inn Express & Suites St. Louis West - Fenton by IHG

Fenton

Donna

$87 nightly

$100 total

Nov 1 - Nov 2

Total with taxes and fees

An indoor swimming pool with clear water, a tiled border, and a no diving sign.

A lobby with patterned orange chairs, a round table with a decorative vase, and two hanging lamps.

A modern kitchen with a central island, bar stools, and a patterned rug.

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

8. Hampton Inn St. Louis/Chesterfield

Chesterfield

Cynthia

$102 nightly

$118 total

Oct 11 - Oct 12

Total with taxes and fees

A hotel named Sonesta ES Suites with a staircase leading to the entrance, surrounded by well-maintained greenery and red flowers.

A compact kitchen with a refrigerator, microwave, stove, and a small dining table with two stools.

A 'check in' sign in front of a building with a landscaped garden and a lamp post.

A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area with a table and chairs.

9. Sonesta ES Suites St. Louis - Chesterfield

Chesterfield

Dennis

$99 nightly

$114 total

Nov 1 - Nov 2

Total with taxes and fees

A modern kitchen with stainless steel appliances, a central island with stools, and a wine cooler.

A Hilton Garden Inn with a brick facade, a covered entrance, and landscaped gardens.

A swimming pool with a lifebuoy on the wall, poolside chairs, and a sign with pool rules.

A spacious lobby with a seating area, a reception desk, and a kitchen area.

10. Hilton Garden Inn Chesterfield

Chesterfield

Bryan

$102 nightly

$118 total

Nov 1 - Nov 2

Total with taxes and fees

A swimming pool with a metal ladder, surrounded by chairs and large windows offering a view of the sunset.

A modern hotel lobby with a cityscape view, a reception desk, and ambient lighting.

A modern hotel lobby with a seating area, a desk, and large windows offering a view of the outside.

A modern hotel with a prominent 'La Quinta' sign, large windows, and a covered entrance area.

11. La Quinta Inn & Suites by Wyndham St Louis Route 66

St. Louis

Alicia

$95 nightly

$111 total

Oct 4 - Oct 5

Total with taxes and fees

A modern kitchen with white cabinets, a central island, and a patterned rug.

A swimming pool with lounge chairs and a fence.

A modern living room with a sofa, ottoman, and coffee table, a dining area with a table and chairs, and a kitchen with a refrigerator and microwave.

A spacious lobby with a reception desk, seating area, and a fireplace.

12. Homewood Suites by Hilton St. Louis-Chesterfield

Chesterfield

Sekar Reddy

$107 nightly

$124 total

Oct 11 - Oct 12

Total with taxes and fees

A modern living area with a sofa, armchairs, a coffee table, and a kitchen in the background.

A large indoor pool with clear glass walls, a tiled edge, and a seating area with chairs and tables.

A modern living room with a sectional sofa, a round coffee table, and large windows offering a view of the city.

A modern lobby with a reception desk, seating area, and a fireplace.

13. Best Western St. Louis Inn

St. Louis

Harold

$79 nightly

$91 total

Oct 8 - Oct 9

Total with taxes and fees

A modern hotel with a prominent entrance, a landscaped courtyard, and a well-lit facade.

An outdoor patio area with a stone wall, seating, and a table.

A spacious lobby with a sectional sofa, a coffee table, and a round table with chairs. There is a large abstract painting on the wall and a staircase in the background.

A modern conference room with a large table, four chairs, a computer, and a bookshelf with books and a framed picture.

14. AC Hotel by Marriott St. Louis Chesterfield

Chesterfield

Richard

$159 nightly

$184 total

Oct 11 - Oct 12

Total with taxes and fees

An outdoor patio area with wicker furniture and a central fire feature.

A modern hotel lobby with a reception desk, seating area, and a television screen displaying a map.

A Courtyard Marriott hotel with a parking lot and a green shuttle service.

A hotel room with a bed, a sofa, a desk, and a chair.

15. Courtyard by Marriott St. Louis Chesterfield

Chesterfield

Kelly

$116 nightly

$135 total

Oct 18 - Oct 19

Total with taxes and fees

A modern interior with a high ceiling, large windows, and a brick wall. There are orange chairs and a green sofa with orange cushions.

A hotel room with a bed, a desk, a television, a sofa, and a lamp.

A lobby with a reception desk, seating area, and large windows.

A modern indoor space with a large window, a seating area with sofas and chairs, and a dining area with tables and chairs.

16. Pear Tree Inn St. Louis Arnold

Arnold

Lynda

$90 nightly

$104 total

Oct 7 - Oct 8

Total with taxes and fees

A modern kitchen area with a breakfast bar, a coffee machine, and a refrigerator displaying menu options.

A coffee station with two coffee machines and a display of coffee pods and cups.

A hotel room with two beds, a blue sofa, a small table, and a kitchenette.

A pool area with a blue pool lift chair, a pool user capacity sign, and a tiled wall.

17. Holiday Inn Express & Suites St. Louis - Chesterfield by IHG

Chesterfield

Steven

$111 nightly

$129 total

Nov 1 - Nov 2

Total with taxes and fees

A hotel lobby with a hot tub, a pool, and outdoor seating.

A large conference room with rows of chairs, a patterned carpet, and a ceiling with recessed lighting and a chandelier.

A lobby with seating areas, a reception desk, and a view of the lobby in the background.

A modern lounge area with grey armchairs, a sofa, a TV, and a bookshelf.

18. Drury Plaza Hotel St. Louis Creve Coeur

Creve Coeur

Eryn

$123 nightly

$143 total

Nov 2 - Nov 3

Total with taxes and fees

A spacious lobby with a brown leather sofa, multiple chairs, a coffee table with a skull decoration, and a large chandelier.

A hotel room with a large bed, a desk with a chair, a television, a mirror, and a wardrobe.

An indoor tennis court with multiple courts, a net, and players.

A hotel room with orange furniture, a glass coffee table, a dining area with a table and chairs, and a patterned carpet.

19. DoubleTree by Hilton Hotel St. Louis - Chesterfield

Chesterfield

Saranne

$139 nightly

$161 total

Oct 25 - Oct 26

Total with taxes and fees

A hotel room with a bed, a sofa, a coffee table, and wall art.

A hotel lobby with a reception desk, seating area, and a large potted plant.

An indoor swimming pool with a clear view of the outside, a metal ladder, and a ceiling with recessed lighting.

A Sleep Inn & Suites hotel with a modern brick facade, a covered entrance, and a parking lot.

20. Sleep Inn & Suites O'Fallon MO - Technology Drive

O'Fallon

Tim

$77 nightly

$90 total

Oct 4 - Oct 5

Total with taxes and fees

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Top Winchester Hotel Reviews

Drury Plaza Hotel St. Louis Union Station

10/10 Excellent

"It was a great hotel located in a very neat part of town. It was clean and fit our needs perfectly."

Hollywood Casino & Hotel St. Louis

10/10 Excellent

"Walking distance to Lambo"

Pear Tree Inn St. Louis Near Union Station

8/10 Good

"Location of hotel was perfect since I was attending soccer game which stadium was across the street"

Hampton Inn St. Louis-Downtown (At the Gateway Arch)

10/10 Excellent

"Paula at the front desk was amazing! Felt save in the private parking garage. Everything needed a key to get in, to keep random outsiders from entering."

Courtyard by Marriott St. Louis Downtown/Convention Center

8/10 Good

"TV on in room when we arrived. There was no remote to turn tv off. Called down to"

21C Museum Hotel St Louis

10/10 Excellent

"Room clean. Staff friendly."

Renaissance St. Louis Airport Hotel

10/10 Excellent

"Hotel is beautiful within itself"

Home2 Suites by Hilton St. Louis Downtown

8/10 Good

"Clean rooms, friendly helpful staff, nice complimentary breakfast and nighttime security make this hotel an incredible value. The location is great too. The beds and pillows are not comfortable but they were very clean. This is not really an issue if traveling for business. I recommend this property."

More cheap stays in Winchester

Best Western St. Louis Inn

6224 Heimos Industrial Park Dr St. Louis MO

$79 nightly

$91 total

Oct 8 - Oct 9

Total with taxes and fees

Tru By Hilton St. Louis Downtown

1221 Locus Street St. Louis MO

$89 nightly

$105 total

Nov 1 - Nov 2

Total with taxes and fees

7.8/10 Good! (996 reviews)

Pear Tree Inn St. Louis Airport

10810 Pear Tree Ln St. Ann MO

$90 nightly

$106 total

Oct 11 - Oct 12

Total with taxes and fees

The West End

4215 Lindell Blvd St. Louis MO

$105 nightly

$119 total

Oct 4 - Oct 5

Total with taxes and fees

Hampton Inn St. Charles St. Peters

3720 W Clay St St. Charles MO

$119 nightly

$136 total

Oct 25 - Oct 26

Total with taxes and fees

AC Hotel St. Louis Clayton

227 South Central Ave St. Louis MO

$128 nightly

$150 total

Oct 11 - Oct 12

Total with taxes and fees

Hotels in Winchester with star-rating

Frequently asked questions

What is the best area to stay in Winchester?

The best area to stay in Winchester is the area around Manchester Road, particularly near the intersection with Clarkson Road, as it offers the most convenience for visitors.This area is primarily a commercial district, characterized by a concentration of shopping centers, dining establishments, and lodging options. It serves as Winchester's main commercial corridor, making it an excellent base for accessing amenities and local attractions.For families, this area is particularly suitable due to the abundance of family-friendly restaurants and easy access to shopping for necessities. The proximity to various services means less travel time and more convenience for those with children.Travelers looking for a comfortable and convenient stay will appreciate the selection of hotels in this area.

When is the best time to go to Winchester?

The best time to go to Winchester, Missouri, is typically during the spring (April to May) and fall (September to October) months. These seasons offer the most pleasant weather for outdoor activities and exploring the area.For those planning to visit during spring, you can expect mild temperatures, blooming flowers, and comfortable conditions for walking or enjoying local parks. It's an excellent time for couples looking for a relaxed getaway, as the weather is conducive to leisurely strolls and dining al fresco without the intense heat of summer.Travelers who prefer cooler temperatures and autumn foliage will find fall to be an ideal time. The crisp air and colorful landscapes provide a beautiful backdrop for exploring the region.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Winchester.

How much is the nightly rate at a Winchester hotel?

Prices for hotels in Winchester often vary, but you can find a great deal from $91 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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Lodging

Find hotels in Winchester, MO from $91

Upfront pricing

Treat yourself

Be picky

Go beyond your typical stay in Winchester

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Winchester hotels

1. Drury Inn & Suites Southwest St. Louis

2. Hyatt Place St. Louis/Chesterfield

3. Drury Plaza Hotel St. Louis Chesterfield

4. Best Western Plus Fenton

5. The Wildwood Hotel

6. Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

7. Holiday Inn Express & Suites St. Louis West - Fenton by IHG

8. Hampton Inn St. Louis/Chesterfield

9. Sonesta ES Suites St. Louis - Chesterfield

10. Hilton Garden Inn Chesterfield

11. La Quinta Inn & Suites by Wyndham St Louis Route 66

12. Homewood Suites by Hilton St. Louis-Chesterfield

13. Best Western St. Louis Inn

14. AC Hotel by Marriott St. Louis Chesterfield

15. Courtyard by Marriott St. Louis Chesterfield

16. Pear Tree Inn St. Louis Arnold

17. Holiday Inn Express & Suites St. Louis - Chesterfield by IHG

18. Drury Plaza Hotel St. Louis Creve Coeur

19. DoubleTree by Hilton Hotel St. Louis - Chesterfield

20. Sleep Inn & Suites O'Fallon MO - Technology Drive

Top Winchester Hotel Reviews

Drury Plaza Hotel St. Louis Union Station

Hollywood Casino & Hotel St. Louis

Pear Tree Inn St. Louis Near Union Station

Hampton Inn St. Louis-Downtown (At the Gateway Arch)

Courtyard by Marriott St. Louis Downtown/Convention Center

21C Museum Hotel St Louis

Renaissance St. Louis Airport Hotel

Home2 Suites by Hilton St. Louis Downtown

More cheap stays in Winchester

Best Western St. Louis Inn

Tru By Hilton St. Louis Downtown

Pear Tree Inn St. Louis Airport

The West End

Hampton Inn St. Charles St. Peters

AC Hotel St. Louis Clayton

Hotels in Winchester with star-rating

Frequently asked questions

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