Hotels in Winchester

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Where to stay in Winchester?

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 with a covered entrance, brick facade, and a parking area.

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.

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

Fenton

$94

$109 total

includes taxes & fees

Aug 26 - Aug 27

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 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.

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

Drury Inn & Suites Southwest St. Louis

Valley Park

$119

$139 total

includes taxes & fees

Aug 30 - Aug 31

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

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

The Wildwood Hotel

Wildwood

$88

$103 total

includes taxes & fees

Sep 7 - Sep 8

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

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.

A Holiday Inn Express & Suites building with a prominent sign, a covered entrance, and a flagpole with an American flag.

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

Fenton

$97

$112 total

includes taxes & fees

Aug 30 - Aug 31

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

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

Sonesta ES Suites St. Louis - Chesterfield

Chesterfield

$99

$115 total

includes taxes & fees

Aug 26 - Aug 27

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

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

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

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

Hyatt Place St. Louis/Chesterfield

Chesterfield

$117

$136 total

includes taxes & fees

Sep 13 - Sep 14

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

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

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.

Drury Plaza Hotel St. Louis Chesterfield

Chesterfield

$130

$151 total

includes taxes & fees

Aug 30 - Aug 31

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

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

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

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

Best Western Plus Fenton

Fenton

$95

$110 total

includes taxes & fees

Aug 30 - Aug 31

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.

Hampton Inn St. Louis/Chesterfield

Chesterfield

$102

$118 total

includes taxes & fees

Sep 20 - Sep 21

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.

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

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

Fairfield Inn & Suites by Marriott St. Louis Chesterfield

Chesterfield

$119

$138 total

includes taxes & fees

Aug 30 - Aug 31

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

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

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.

Holiday Inn St Louis SW - Route 66 by IHG

St. Louis

$118

$140 total

includes taxes & fees

Sep 13 - Sep 14

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

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

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

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

Courtyard by Marriott St. Louis Chesterfield

Chesterfield

$125

$146 total

includes taxes & fees

Aug 30 - Aug 31

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

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

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.

Drury Plaza Hotel St. Louis Creve Coeur

Creve Coeur

$128

$149 total

includes taxes & fees

Sep 13 - Sep 14

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

A modern hotel lobby with a sofa, chairs, a small table, and a bar area.

A building entrance with glass doors, stone accents, and potted plants.

A hotel room with two beds, a blue sofa, a lamp, and abstract art on the walls.

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

Chesterfield

$114

$133 total

includes taxes & fees

Aug 30 - Aug 31

A modern lobby with a stone fireplace, blue sofas, and potted plants.

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

An indoor swimming pool with clear water, surrounded by lounge chairs and a tiled deck.

A modern kitchen with a coffee machine, microwave, and refrigerator. There is a dining area with tables and chairs.

Comfort Suites St. Louis - Sunset Hills

St. Louis

$127

$147 total

includes taxes & fees

Sep 1 - Sep 2

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

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

Best Western St. Louis Inn

St. Louis

$71

$82 total

includes taxes & fees

Sep 17 - Sep 18

A hotel with multiple floors, a parking lot, and a body of water in front.

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

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

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

Hilton Garden Inn Chesterfield

Chesterfield

$118

$138 total

includes taxes & fees

Sep 20 - Sep 21

A spacious lobby with modern seating, a reception desk, and large windows offering views of the parking area.

A spacious indoor area with a high ceiling and large windows, featuring multiple seating areas with sofas and chairs, and a visible outdoor view through the windows.

A spacious indoor area with multiple wooden tables and chairs, large windows, and a high ceiling with exposed beams.

A seating area with three grey armchairs and a central glass-top table, a wooden floor, and a view of parked cars through large windows.

Pear Tree Inn St. Louis Airport

St. Ann

$90

$106 total

includes taxes & fees

Aug 30 - Aug 31

A large hotel with a prominent tower and multiple parking areas.

A lobby with a large screen displaying "Hollywood Casino" and "Wood Casino" signs, multiple chandeliers, and a polished floor.

A crowded indoor space with a chandelier, brick walls, and tables where people are seated and standing.

A spacious lobby with a patterned carpet, a reception desk, and a seating area with a sofa and chairs.

Hollywood Casino & Hotel St. Louis

Riverport

$86

$130 total

includes taxes & fees

Aug 26 - Aug 27

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

A modern dining area with multiple tables and chairs, large windows offering a view of the outdoors, and a mix of natural and artificial lighting.

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.

La Quinta Inn & Suites by Wyndham St Louis Route 66

St. Louis

$105

$122 total

includes taxes & fees

Sep 13 - Sep 14

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Go beyond your typical stay in Winchester

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Check out reviews of Winchester hotels guests love

Pear Tree Inn St. Louis Airport

8/10 Good

"Room was clean and nice nothing out of the ordinary. Breakfast was good and staff was very pleasant. Location was great for our need, we only needed the night and it was 2 blocks from our rental car pickup."

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

10/10 Excellent

"It was just a beautiful environment with all around gorgeous sceneries. The rooftop was great. The surrounding area was great. The staff was very helpful, even allowing me to use the charger overnight because I had left mine, which I hope they don’t get in trouble for that because it’s very helpful."

21C Museum Hotel St Louis

10/10 Excellent

"Amazing fitness facilities! Staff was incredible. Great food too. Only complaint was the pillows were not very comfortable and the rooms feel cramped. But very minor issues."

Drury Plaza Hotel St. Louis at the Arch

8/10 Good

"Wonderful front desk staff."

Clayton Plaza Hotel & Extended Stay

10/10 Excellent

"Modern features and a full restaurant style breakfast included. It’s the only place we stay when visiting the area."

Magnolia Hotel St. Louis, a Tribute Portfolio Hotel

10/10 Excellent

"Staff were friendly and helpful. Room and common areas were clean. We like that our dog was able to stay with us for no extra charge. The only negative thing I'd mention is that the TV in our room kept going in and out. The picture and audio were glitching. Not the end of the world though. We both noted that the mattress and pillows were quite comfortable. I'm definitely going to be staying here while visiting again."

The Royal Sonesta Chase Park Plaza St. Louis

10/10 Excellent

"Great spot - always love staying"

Pear Tree Inn St. Louis Near Union Station

10/10 Excellent

"It was a good location and very good experience"

Hyatt Regency St. Louis at The Arch

10/10 Excellent

"Great location steps from the arch. excellent service and varied dining options."

Frequently asked questions

What hotels do travelers like in Winchester?

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

Can I book a refundable hotel in Winchester?

If you want the flexibility to change your plans to Winchester, most hotels offer refundable* rates you can book. You can see these properties by searching our site and using the "fully refundable" filter to narrow down the results.

What will the weather in Winchester be like during my vacation?

July and August are typically the warmest months in Winchester when the average temp is 76°F. January and February are the coldest months when the average temperature is 38°F. May and April are the months with the most rain.

Why should I book my Winchester accommodation with Hotels.com?

There are lots of reasons to book your Winchester trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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