Hotels in Winchester

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Top 5 hotels in Winchester at a glance

Hyatt Place St. Louis/Chesterfield — 3-star hotel in Chesterfield. Guest rating: 9.6/10 — Exceptional.
Holiday Inn Express & Suites St. Louis West - Fenton by IHG — 3-star hotel in Fenton. Guest rating: 8.8/10 — Excellent.
Drury Inn & Suites Southwest St. Louis — 3-star hotel in Valley Park. Guest rating: 9.6/10 — Exceptional.
Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham — 3-star hotel in Fenton. Guest rating: 7.8/10 — Good.
The Wildwood Hotel — 3.5-star hotel in Wildwood. Guest rating: 9.2/10 — Wonderful.

Where to stay in Winchester?

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Winchester on Hotels.com. These Winchester hotels consistently deliver on comfort, location and traveler experience. Last updated on August 27, 2026.

Room (2 Queen beds with sofa bed) | Premium bedding, desk, laptop workspace, blackout drapes

Hyatt Place St. Louis/Chesterfield

Chesterfield

CNY786

CNY911 total

includes taxes & fees

Sep 13 - Sep 14

In-room safe, desk, laptop workspace, iron/ironing board

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

Fenton

CNY652

CNY753 total

includes taxes & fees

Sep 27 - Sep 28

Drury Inn & Suites Southwest St. Louis

Valley Park

CNY800

CNY936 total

includes taxes & fees

Sep 3 - Sep 4

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

Fenton

CNY634

CNY732 total

includes taxes & fees

Aug 30 - Aug 31

Suite, 1 King Bed, Jetted Tub | Jetted tub

The Wildwood Hotel

Wildwood

CNY593

CNY691 total

includes taxes & fees

Aug 31 - Sep 1

Desk, blackout drapes, iron/ironing board, cribs (free)

Drury Plaza Hotel St. Louis Chesterfield

Chesterfield

CNY874

CNY1,013 total

includes taxes & fees

Sep 6 - Sep 7

Hypo-allergenic bedding available, desk, laptop workspace

Best Western Plus Fenton

Fenton

CNY667

CNY770 total

includes taxes & fees

Sep 7 - Sep 8

Room, 1 King Bed | Desk, laptop workspace, blackout drapes, iron/ironing board

Fairfield Inn & Suites by Marriott St. Louis Chesterfield

Chesterfield

CNY800

CNY928 total

includes taxes & fees

Aug 30 - Aug 31

Blackout drapes, soundproofing, iron/ironing board, cribs (free)

Sonesta ES Suites St. Louis - Chesterfield

Chesterfield

CNY669

CNY775 total

includes taxes & fees

Aug 30 - Aug 31

Hampton Inn St. Louis/Chesterfield

Chesterfield

CNY684

CNY793 total

includes taxes & fees

Sep 20 - Sep 21

Presidential Suite, 1 King Bed, Non Smoking | Premium bedding, down comforters, in-room safe, desk

DoubleTree by Hilton Hotel St. Louis - Chesterfield

Chesterfield

CNY766

CNY889 total

includes taxes & fees

Sep 19 - Sep 20

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

Chesterfield

CNY766

CNY891 total

includes taxes & fees

Aug 30 - Aug 31

Drury Plaza Hotel St. Louis Creve Coeur

Creve Coeur

CNY867

CNY1,008 total

includes taxes & fees

Sep 27 - Sep 28

Premium bedding, pillowtop beds, desk, laptop workspace

Courtyard by Marriott St. Louis Chesterfield

Chesterfield

CNY794

CNY924 total

includes taxes & fees

Sep 5 - Sep 6

1 bedroom, hypo-allergenic bedding available, memory foam beds, desk

Comfort Suites St. Louis - Sunset Hills

St. Louis

CNY851

CNY989 total

includes taxes & fees

Sep 7 - Sep 8

2 restaurants; breakfast, lunch, and dinner served

Holiday Inn St Louis SW - Route 66 by IHG

St. Louis

CNY773

CNY920 total

includes taxes & fees

Sep 27 - Sep 28

La Quinta Inn & Suites by Wyndham St Louis Route 66

St. Louis

CNY703

CNY817 total

includes taxes & fees

Sep 13 - Sep 14

Hilton Garden Inn Chesterfield

Chesterfield

CNY765

CNY890 total

includes taxes & fees

Sep 20 - Sep 21

Room, 2 Queen Beds, Accessible, Non Smoking (Mobility, Tub W/Grab Bars) | Desk, laptop workspace, iron/ironing board, cribs (free)

Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, iron/ironing board, cribs (free)

Wingate by Wyndham St. Louis Airport

St. Ann

CNY769

CNY905 total

includes taxes & fees

Sep 7 - Sep 8

Room | In-room safe, blackout drapes, iron/ironing board, cribs (free)

Hampton Inn & Suites St. Louis/South I-55

St. Louis

CNY711

CNY818 total

includes taxes & fees

Sep 20 - Sep 21

View all properties

Go beyond your typical stay in Winchester

Pet friendly

Apartment

Pool

Family friendly

Hot tub

Cottage

Check out reviews of Winchester hotels guests love

Clayton Plaza Hotel & Extended Stay

10/10 Excellent

"The hotel was excellent, clean, and well located to area attractions. The breakfast was very good. Parking was $6 per day which was very reasonable compared to other hotels in the area. The hotel is close to metro lines and Washington University. The staff was very helpful when we inquired about a couple things. We would definitely stay here again."

Hyatt Regency St. Louis at The Arch

10/10 Excellent

"The lady, I did not catch her name, who checked us in was so kind! She was such a bright light and was so fun to chat with while getting checked in. They have amazing staff and the room was clean, the beds are so comfortable!"

Drury Plaza Hotel St. Louis at the Arch

10/10 Excellent

"Beautiful view, could see arch from room window. Loved room - clean, comfortable, shower was hot with great water pressure. Food was good and the wait staff were friendly. Laverne was the best. The drink and snack time from 5:30pm to 7pm was fantastic. Easily dinner if you want and 3 drinks more than enough included with your stay. Parking was convenient, very easy in and out. Easy location to drive places. Location was fantastic. The Arch National Park was right next door and the old courthouse museum across the street. It was fun to walk around and explore. My only complaint was no adult only time in the pool area. Every time my husband and I checked it out, it was full of kids yelling and running around. We did try to enjoy our last night, but it was hard to enjoy. The entire time we were in the hot tub, there were multiple children under 8 in the tub. No adult paying attention to what they were doing. Almost kicked in the face by a 4 yo trying to use it as a kiddie swimming pool, legs being bumped and toes stepped on. Went and sat at table to see if maybe would leave since there before us but still running back and forth between hot tub and pool after 9pm, so headed back to our room. Also 2nd hot tub was broke, not hot and jets not working. Was a great fun place to stay despite the pool situation"

21C Museum Hotel St Louis

8/10 Good

"Rooms are spacious, clean, and stylish."

River City Casino & Hotel

10/10 Excellent

"Kellie & Emoni at the check-in were so friendly & helpful! The room was comfortable, the walk-in shower is wonderful with both rain & normal shower heads. For an older hotel, I found it to be well appointed with plenty of storage & furniture. The mattress was pretty firm which we were very happy with. The casino is huge with lots & lots of various slots, & table games. No luck here but not unexpected! The cigarette smoke from that side of the casino is pretty evident in the non-smoking portion."

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

10/10 Excellent

"Wasn't sure what to expect when we pulled into hotel but looks can be deceiving. Staff was great, check in easy, room was clean, cold, amazing beds, even the shampoo and conditioner were fantastic. After a 16 hour drive it was a welcome and great choice."

Marriott St. Louis Grand

10/10 Excellent

"Staff was friendly and helped extremely well. My stay was made great and the convention was great"

Forest Park Hotel by MDR

8/10 Good

"Free parking, clean big room, with microwave and fridge and affordable."

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."

Frequently asked questions

How much does a hotel room cost in Winchester?

You can find top hotels in Winchester from CNY612 with options to suit your budget and needs. If you're looking for an affordable hotel in Winchester that meets all of your requirements, just sort hotels by "Price: low to high" after applying your filters when searching on Hotels.com.

How can I find deals and earn rewards at Winchester hotels?

Discover great deals on Winchester hotel stays with Hotels.com. You can also look at hotel prices mid-week or during the low season to find off-peak deals. And make sure to check out our last-minute deals on Winchester hotels.

Can I book Winchester hotels with free cancellation?

It's easy to book a refundable Winchester hotel on Hotels.com. Simply filter hotels by "Property cancellation options" and select "Fully refundable property". Most hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.

What are some popular hotels in central Winchester?

If you're looking for hotels in central Winchester, check out Drury Plaza Hotel St. Louis Chesterfield and The Wildwood Hotel. Travelers love Drury Plaza Hotel St. Louis Chesterfield for its location, as well as the outdoor pool, hot tub and restaurant this hotel offers. The Wildwood Hotel is another popular central hotel with an indoor pool, a hot tub and a free continental breakfast. Creve Coeur is a central neighborhood for your Winchester vacation.

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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