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

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

An indoor swimming pool with a hot tub, lounge chairs, and a tiled floor.

1. Drury Inn & Suites Southwest St. Louis

Valley Park

Randy

$115 nightly

$135 total

Oct 5 - Oct 6

Total with taxes and fees

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

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

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

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

2. Drury Plaza Hotel St. Louis Chesterfield

Chesterfield

Cassandra

$130 nightly

$151 total

Oct 5 - Oct 6

Total with taxes and fees

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

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.

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

3. The Wildwood Hotel

Wildwood

Ramona

$101 nightly

$118 total

Oct 21 - Oct 22

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

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

4. Hyatt Place St. Louis/Chesterfield

Chesterfield

Chelsea

$126 nightly

$146 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 lobby with patterned orange chairs, a round table with a decorative vase, and two hanging lamps.

A snack display with various packaged snacks and a 'Treats' sign above.

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

5. 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.

6. Best Western Plus Fenton

Fenton

Brian

$91 nightly

$105 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 snack bar with shelves of chips, candies, and bottled water.

An indoor swimming pool with clear water, a diving board, and a seating area with tables and chairs.

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

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

Chesterfield

Thomas Kent

$107 nightly

$124 total

Oct 18 - Oct 19

Total with taxes and fees

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

A hotel room with a flat-screen TV, a wooden cabinet, a light-colored sofa, a matching ottoman, and a small table.

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.

8. 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.

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

$89 nightly

$103 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 swimming pool with a lifebuoy on the wall, poolside chairs, and a sign with pool rules.

A spacious living area with a fireplace, a television mounted above it, and a comfortable seating arrangement.

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

10. Hilton Garden Inn Chesterfield

Chesterfield

Bryan

$102 nightly

$118 total

Oct 11 - Oct 12

Total with taxes and fees

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

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

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 swimming pool with lounge chairs and a fence.

11. Homewood Suites by Hilton St. Louis-Chesterfield

Chesterfield

Sekar Reddy

$110 nightly

$127 total

Oct 11 - Oct 12

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.

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

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

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

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

13. Marriott St. Louis West

St. Louis

Darrel

$116 nightly

$135 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 'check in' sign in front of a building with a landscaped garden and a lamp post.

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

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

14. Sonesta ES Suites St. Louis - Chesterfield

Chesterfield

Dennis

$99 nightly

$114 total

Nov 1 - Nov 2

Total with taxes and fees

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

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

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

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

15. Drury Plaza Hotel St. Louis Creve Coeur

Creve Coeur

Eryn

$124 nightly

$144 total

Oct 8 - Oct 9

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

16. DoubleTree by Hilton Hotel St. Louis - Chesterfield

Chesterfield

Saranne

$139 nightly

$161 total

Oct 25 - Oct 26

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 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.

17. Courtyard by Marriott St. Louis Chesterfield

Chesterfield

Kelly

$116 nightly

$135 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 hotel room with a large bed, a desk, a chair, a TV, and a window with curtains.

18. Best Western St. Louis Inn

St. Louis

Harold

$75 nightly

$86 total

Oct 6 - Oct 7

Total with taxes and fees

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

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

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.

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

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

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

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

$80 nightly

$94 total

Oct 4 - Oct 5

Total with taxes and fees

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Top Winchester Hotel Reviews

Renaissance St. Louis Airport Hotel

10/10 Excellent

"Hotel is beautiful within itself"

Pear Tree Inn St. Louis Airport

10/10 Excellent

"The service is great and fast! Room was clean and hotel was very quiet and peaceful."

Pear Tree Inn St. Louis Near Union Station

10/10 Excellent

"Our room was very clean. We loved how calm our stay was. We appreciated how welcoming was Ms. Doris at the front desk. We felt valued as the guests, all our questions were answered. We definitely will be back again!"

Drury Plaza Hotel St. Louis Union Station

8/10 Good

"The staff was friendly and helpful. As we were checking in a busload showed up and staff had us wait a minute, but thanked us and gave us free parking. When our air conditioning wasn't working properly, they gave us advice on getting it to work and brought us a fan. It worked after the advice. They had a great perk of drinks and appetizers, but we didn't have time to partake. Breakfast was delicious. We would definitely visit again!"

Drury Plaza Hotel St. Louis at the Arch

8/10 Good

"The location is fantastic if visiting the Arch. The staff and amenities are amazing. Be prepared to pay $50 to park in the hotel parking garage that isn't very secure nor accessible for anything larger than a typical sized vehicle."

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."

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)

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

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

9.2/10 Wonderful! (3,260 reviews)

Comfort Suites St Charles - St Louis

1400 S 5th St St. Charles MO

$98 nightly

$112 total

Nov 1 - Nov 2

Total with taxes and fees

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

The West End

4215 Lindell Blvd St. Louis MO

$106 nightly

$120 total

Oct 4 - Oct 5

Total with taxes and fees

8.6/10 Excellent! (659 reviews)

Hampton Inn St. Charles St. Peters

3720 W Clay St St. Charles MO

$119 nightly

$136 total

Oct 4 - Oct 5

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. Drury Plaza Hotel St. Louis Chesterfield

3. The Wildwood Hotel

4. Hyatt Place St. Louis/Chesterfield

5. Hampton Inn St. Louis/Chesterfield

6. Best Western Plus Fenton

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

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

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

10. Hilton Garden Inn Chesterfield

11. Homewood Suites by Hilton St. Louis-Chesterfield

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

13. Marriott St. Louis West

14. Sonesta ES Suites St. Louis - Chesterfield

15. Drury Plaza Hotel St. Louis Creve Coeur

16. DoubleTree by Hilton Hotel St. Louis - Chesterfield

17. Courtyard by Marriott St. Louis Chesterfield

18. Best Western St. Louis Inn

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

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

Top Winchester Hotel Reviews

Renaissance St. Louis Airport Hotel

Pear Tree Inn St. Louis Airport

Pear Tree Inn St. Louis Near Union Station

Drury Plaza Hotel St. Louis Union Station

Drury Plaza Hotel St. Louis at the Arch

Home2 Suites by Hilton St. Louis Downtown

Forest Park Hotel by MDR

More cheap stays in Winchester

Best Western St. Louis Inn

Tru By Hilton St. Louis Downtown

Pear Tree Inn St. Louis Airport

Comfort Suites St Charles - St Louis

The West End

Hampton Inn St. Charles St. Peters

Hotels in Winchester with star-rating

Frequently asked questions

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