Top 10 Hotels in Winchester, MO (from $86) 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 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.

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

1. Drury Inn & Suites Southwest St. Louis

Valley Park

Randy

$115 nightly

$135 total

Oct 8 - Oct 9

Total with taxes and fees

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

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

A formal dining table set for six with a vase of white flowers, candles, and a view of buildings through large windows.

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

2. The Wildwood Hotel

Wildwood

Ramona

$101 nightly

$118 total

Oct 21 - Oct 22

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.

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

Fenton

Dashaun

$94 nightly

$109 total

Oct 1 - Oct 2

Total with taxes and fees

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

A buffet setup with various food items and a decorative vase of flowers.

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

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

4. Drury Plaza Hotel St. Louis Chesterfield

Chesterfield

Cassandra

$130 nightly

$151 total

Oct 25 - Oct 26

Total with taxes and fees

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

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

A hotel room with two beds, a sofa, a small table, a lamp, and a framed abstract painting on the wall.

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

5. Hyatt Place St. Louis/Chesterfield

Chesterfield

Chelsea

$130 nightly

$150 total

Oct 4 - Oct 5

Total with taxes and fees

A hotel reception area with a counter, coffee machines, a refrigerated display, and artwork on the wall.

A reception desk with a wooden finish, a clock, and a sign for Marriott Bonvoy.

A hotel room with a bed, desk, TV, and a view of the outdoors.

A snack bar with shelves of chips, candies, and bottled water.

6. Fairfield Inn & Suites by Marriott St. Louis Chesterfield

Chesterfield

Thomas Kent

$107 nightly

$124 total

Oct 18 - Oct 19

Total with taxes and fees

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

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.

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

7. Hampton Inn St. Louis/Chesterfield

Chesterfield

Ashley

$102 nightly

$118 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 outdoor patio area with a fire pit, black metal chairs, and a blue umbrella.

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

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

8. Best Western Plus Fenton

Fenton

Brian

$91 nightly

$105 total

Oct 4 - Oct 5

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.

A coffee station with two coffee machines, a shelf with coffee cups, and a storage area with boxes and a thermos.

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

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

Fenton

Donna

$97 nightly

$112 total

Oct 25 - Oct 26

Total with taxes and fees

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

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.

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

10. Hilton Garden Inn Chesterfield

Chesterfield

Brian

$102 nightly

$118 total

Oct 11 - Oct 12

Total with taxes and fees

A modern bar area with high ceilings, bar stools, and a well-stocked liquor display.

A gym with treadmills, elliptical machines, and weight machines.

A swimming pool surrounded by lush greenery, with blue lounge chairs and a staircase leading to a building.

An outdoor patio with tables and chairs, a staircase, and a building in the background.

11. Marriott St. Louis West

St. Louis

Darrel

$116 nightly

$135 total

Oct 11 - Oct 12

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 hotel reception area with two counters, a vending machine, and a display cabinet with snacks.

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

A hotel room with a living area, kitchenette, and a bed.

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.

13. Sonesta ES Suites St. Louis - Chesterfield

Chesterfield

Dennis

$101 nightly

$117 total

Oct 30 - Oct 31

Total with taxes and fees

A hotel with a covered entrance, a tower with signage, and a landscaped area with planters.

A hotel lobby with multiple seating areas, including round tables and sofas, and a reception desk with a green plant.

A hotel room with purple walls, a flat-screen TV, a bed, a dining table with chairs, a sofa, and a window with curtains.

A covered outdoor seating area with a pergola, surrounded by landscaped bushes and a paved walkway.

14. La Quinta Inn & Suites by Wyndham St. Louis Westport

Westport

Gary

$79 nightly

$92 total

Oct 3 - Oct 4

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 large, multi-story hotel with the name "Doubletree by Hilton" prominently displayed on the facade.

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

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

15. DoubleTree by Hilton Hotel St. Louis - Chesterfield

Chesterfield

Saranne

$139 nightly

$161 total

Oct 25 - Oct 26

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 coffee shop interior with wooden furniture, a coffee bar, and a sign for 'KELSO+BROS Coffee Roasters'.

16. Drury Plaza Hotel St. Louis Creve Coeur

Creve Coeur

Eryn

$124 nightly

$144 total

Oct 8 - Oct 9

Total with taxes and fees

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

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

A hotel room with a large bed, a desk, a chair, a TV, and a window with curtains.

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

17. Best Western St. Louis Inn

St. Louis

Harold

$75 nightly

$86 total

Oct 6 - Oct 7

Total with taxes and fees

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

A modern hotel lobby with a bar area, seating arrangements, and a reception desk.

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

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

18. Courtyard by Marriott St. Louis Chesterfield

Chesterfield

Kelly

$121 nightly

$140 total

Oct 11 - Oct 12

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

A Holiday Inn Express & Suites building with a brick facade, a covered entrance, and a numbered address.

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

Chesterfield

Steven

$114 nightly

$133 total

Oct 4 - Oct 5

Total with taxes and fees

A bar area with a long counter displaying numerous bottles of alcohol and several empty wine glasses lined up.

A restaurant interior with wooden panel walls, hanging light fixtures, and a chalkboard menu. Tables and chairs are arranged for dining.

A modern lobby with a grey sofa, two armchairs, a round table, and a chandelier. There are two posters on the wall and a reception desk in the background.

A gym with various exercise equipment, large windows, and a skylight.

20. Holiday Inn St Louis SW - Route 66 by IHG

St. Louis

Arnaud

$117 nightly

$137 total

Oct 29 - Oct 30

Total with taxes and fees

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Top Winchester Hotel Reviews

Drury Plaza Hotel St. Louis Union Station

10/10 Excellent

"Breakfast was amazing. Great!"

Pear Tree Inn St. Louis Near Union Station

8/10 Good

"Great"

Courtyard by Marriott St. Louis Downtown/Convention Center

10/10 Excellent

"Everything was clean and accommodating."

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."

Forest Park Hotel by MDR

8/10 Good

"I was only there to sleep and did not use any of the amenities. The noise from the highway and the trains was louder than at most hotels I have stayed at."

Renaissance St. Louis Airport Hotel

10/10 Excellent

"Staff was great! Would come back to stay."

More cheap stays in Winchester

Best Western St. Louis Inn

6224 Heimos Industrial Park Dr St. Louis MO

$75 nightly

$86 total

Oct 6 - Oct 7

Total with taxes and fees

8.4/10 Very Good! (1,166 reviews)

Pear Tree Inn St. Louis Airport

10810 Pear Tree Ln St. Ann MO

$90 nightly

$106 total

Oct 5 - Oct 6

Total with taxes and fees

Comfort Suites St Charles - St Louis

1400 S 5th St St. Charles MO

$93 nightly

$106 total

Oct 12 - Oct 13

Total with taxes and fees

8.4/10 Very Good! (1,011 reviews)

Tru By Hilton St. Louis Downtown

1221 Locus Street St. Louis MO

$98 nightly

$114 total

Oct 6 - Oct 7

Total with taxes and fees

The West End

4215 Lindell Blvd St. Louis MO

$104 nightly

$118 total

Oct 4 - Oct 5

Total with taxes and fees

8.6/10 Excellent! (657 reviews)

Hampton Inn St. Charles St. Peters

3720 W Clay St St. Charles MO

$112 nightly

$128 total

Oct 18 - Oct 19

Total with taxes and fees

8.2/10 Very Good! (1,000 reviews)

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 $86 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 $86

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. The Wildwood Hotel

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

4. Drury Plaza Hotel St. Louis Chesterfield

5. Hyatt Place St. Louis/Chesterfield

6. Fairfield Inn & Suites by Marriott St. Louis Chesterfield

7. Hampton Inn St. Louis/Chesterfield

8. Best Western Plus Fenton

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

10. Hilton Garden Inn Chesterfield

11. Marriott St. Louis West

12. Homewood Suites by Hilton St. Louis-Chesterfield

13. Sonesta ES Suites St. Louis - Chesterfield

14. La Quinta Inn & Suites by Wyndham St. Louis Westport

15. DoubleTree by Hilton Hotel St. Louis - Chesterfield

16. Drury Plaza Hotel St. Louis Creve Coeur

17. Best Western St. Louis Inn

18. Courtyard by Marriott St. Louis Chesterfield

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

20. Holiday Inn St Louis SW - Route 66 by IHG

Top Winchester Hotel Reviews

Drury Plaza Hotel St. Louis Union Station

Pear Tree Inn St. Louis Near Union Station

Courtyard by Marriott St. Louis Downtown/Convention Center

Home2 Suites by Hilton St. Louis Downtown

Forest Park Hotel by MDR

Renaissance St. Louis Airport Hotel

More cheap stays in Winchester

Best Western St. Louis Inn

Pear Tree Inn St. Louis Airport

Comfort Suites St Charles - St Louis

Tru By Hilton St. Louis Downtown

The West End

Hampton Inn St. Charles St. Peters

Hotels in Winchester with star-rating

Frequently asked questions

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