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Our top choices for Winchester hotels

1. The Wildwood Hotel

The Wildwood Hotel
3.5 star property
Wildwood
9.2 out of 10, Wonderful, (1,680 reviews)
"Clean, quiet, great continental breakfast, and close to several places to eat."
United States
Lori
The price is £70
includes taxes & fees
8 Dec - 9 Dec
The Wildwood Hotel

2. Drury Plaza Hotel St. Louis Chesterfield

Drury Plaza Hotel St. Louis Chesterfield
3.0 star property
Chesterfield
9.6 out of 10, Exceptional, (1,325 reviews)
"Really like our stay there"
Canada
messia
The price is £113
includes taxes & fees
18 Nov - 19 Nov
Drury Plaza Hotel St. Louis Chesterfield

3. Hyatt Place St. Louis/Chesterfield

Hyatt Place St. Louis/Chesterfield
3.0 star property
Chesterfield
9.6 out of 10, Exceptional, (1,014 reviews)
"Very nice hotel and lovely room"
United States
Karin
The price is £106
includes taxes & fees
24 Nov - 25 Nov
Hyatt Place St. Louis/Chesterfield

4. Drury Inn & Suites Southwest St. Louis

Drury Inn & Suites Southwest St. Louis
3.0 star property
Valley Park
9.6 out of 10, Exceptional, (1,018 reviews)
"Hotel was very nice and room was comfortable."
United States
Terry
The price is £104
includes taxes & fees
22 Nov - 23 Nov
Drury Inn & Suites Southwest St. Louis

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

Holiday Inn Express & Suites St. Louis West - Fenton by IHG
3.0 star property
Fenton
8.8 out of 10, Excellent, (1,008 reviews)
"The bed was very comfortable."
United States
Ann
The price is £76
includes taxes & fees
13 Dec - 14 Dec
Holiday Inn Express & Suites St. Louis West - Fenton by IHG

6. DoubleTree by Hilton Hotel St. Louis - Chesterfield

DoubleTree by Hilton Hotel St. Louis - Chesterfield
4.0 star property
Chesterfield
8.8 out of 10, Excellent, (1,000 reviews)
"Hotel staff were kind and accommodating. Great stay for a great price!"
United States
April
The price is £96
includes taxes & fees
27 Nov - 28 Nov
DoubleTree by Hilton Hotel St. Louis - Chesterfield

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

Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham
3.0 star property
Fenton
7.8 out of 10, Good, (1,650 reviews)
"Good breakfast and hot tub was nice."
United States
michael
The price is £77
includes taxes & fees
17 Nov - 18 Nov
Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

8. Best Western Plus Fenton

Best Western Plus Fenton
2.5 star property
Fenton
9.0 out of 10, Wonderful, (481 reviews)
"Breakfast was great! Staff was super helpful and friendly, and the room was clean and comfortable."
United States
Brian
The price is £81
includes taxes & fees
15 Nov - 16 Nov
Best Western Plus Fenton

9. Sonesta ES Suites St. Louis - Chesterfield

Sonesta ES Suites St. Louis - Chesterfield
3.0 star property
Chesterfield
8.0 out of 10, Very good, (1,066 reviews)
"Breakfast was great"
United States
Shuntichia
The price is £78
includes taxes & fees
13 Dec - 14 Dec
Sonesta ES Suites St. Louis - Chesterfield

10. Hampton Inn St. Louis/Chesterfield

Hampton Inn St. Louis/Chesterfield
3.5 star property
Chesterfield
8.6 out of 10, Excellent, (1,000 reviews)
"Everything was spotlessly clean, staff were amazing and breakfast was exceptional! Will definitely be starting again!"
United States
Susan
The price is £92
includes taxes & fees
24 Nov - 25 Nov
Hampton Inn St. Louis/Chesterfield

11. Marriott St. Louis West

Marriott St. Louis West
3.5 star property
St. Louis
8.6 out of 10, Excellent, (1,000 reviews)
"In town for a soccer tournament. Staff was very accommodating. Especially Ryan at check in."
United States
Sharon
The price is £93
includes taxes & fees
22 Nov - 23 Nov
Marriott St. Louis West

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

Fairfield Inn & Suites by Marriott St. Louis Chesterfield
3.0 star property
Chesterfield
9.0 out of 10, Wonderful, (1,000 reviews)
"very nice stay. Great room with easy check in ,nice staff, friendly and helpful. Excellent breakfast, with good setup and fresh food."
United States
Charles
The price is £93
includes taxes & fees
22 Nov - 23 Nov
Fairfield Inn & Suites by Marriott St. Louis Chesterfield

13. Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield
3.0 star property
Chesterfield
8.4 out of 10, Very good, (848 reviews)
"We def will be staying here again after our last hotel experience"
United States
Samantha
The price is £93
includes taxes & fees
29 Nov - 30 Nov
Hilton Garden Inn Chesterfield

14. Hollywood Casino & Hotel St. Louis

Hollywood Casino & Hotel St. Louis
3.5 star property
Riverport
8.6 out of 10, Excellent, (2,257 reviews)
"Always love staying here! Rooms are so spacious and comfy"
United States
Shayla
The price is £72
includes taxes & fees
6 Dec - 7 Dec
Hollywood Casino & Hotel St. Louis

15. Courtyard by Marriott St. Louis Chesterfield

Courtyard by Marriott St. Louis Chesterfield
3.0 star property
Chesterfield
9.0 out of 10, Wonderful, (684 reviews)
"The room was beautiful and clean. We enjoyed the pool and the bar while we were there. Great amenities!"
United States
Brittney
The price is £96
includes taxes & fees
21 Nov - 22 Nov
Courtyard by Marriott St. Louis Chesterfield

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

Holiday Inn Express & Suites St. Louis - Chesterfield by IHG
2.5 star property
Chesterfield
9.0 out of 10, Wonderful, (1,000 reviews)
"We drove across America and this property stood out by just having the most comfortable beds and a great breakfast , great staff ."
United States
Terry
The price is £99
includes taxes & fees
22 Nov - 23 Nov
Holiday Inn Express & Suites St. Louis - Chesterfield by IHG

17. Best Western St. Louis Inn

Best Western St. Louis Inn
2.5 star property
St. Louis
8.4 out of 10, Very good, (1,218 reviews)
"Clean rooms good breakfast."
United States
Susan
The price is £65
includes taxes & fees
18 Nov - 19 Nov
Best Western St. Louis Inn

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

La Quinta Inn & Suites by Wyndham St Louis Route 66
3.0 star property
St. Louis
8.4 out of 10, Very good, (1,001 reviews)
"Great place!"
United States
Edward
The price is £82
includes taxes & fees
10 Dec - 11 Dec
La Quinta Inn & Suites by Wyndham St Louis Route 66

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

Sleep Inn & Suites O'Fallon MO - Technology Drive
2.5 star property
O'Fallon
9.0 out of 10, Wonderful, (1,159 reviews)
"Rooms are very clean, the staff is friendly and the location is great. We enjoyed are stay."
United States
Matthew
The price is £71
includes taxes & fees
2 Dec - 3 Dec
Sleep Inn & Suites O'Fallon MO - Technology Drive

20. Pear Tree Inn St. Louis Arnold

Pear Tree Inn St. Louis Arnold
2.5 star property
Arnold
9.4 out of 10, Exceptional, (1,001 reviews)
"Great Place to stay!"
United States
Charlotte
The price is £78
includes taxes & fees
18 Nov - 19 Nov
Pear Tree Inn St. Louis Arnold
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Winchester Hotel Reviews

Frequently Asked Questions

What is the best area to stay in Winchester?

The best area to stay in Winchester is near Manchester Road, which offers convenient access to amenities and attractions.

This area is excellent for those who appreciate accessibility without being directly in the busiest parts of St. Louis. It's characterised by a mix of retail parks, eateries, and business hubs, making it a practical choice for various travellers. You'll find a good selection of hotels here, many of which are modern and offer excellent facilities.

For business travellers, staying near Manchester Road is particularly beneficial. Its proximity to major roadways like I-270 allows for easy commutes to corporate offices and business parks in the wider St. Louis metropolitan area. Many hotels in this vicinity cater to business needs with features like meeting rooms and high-speed internet.

Families visiting Winchester will also find this area suitable. There are numerous dining options ranging from casual family restaurants to more upscale choices.

When is the best time to go to Winchester?

The best time to go to Winchester, Missouri, is during the spring (late March to May) and autumn (September to November) months.

These seasons offer pleasant weather, with moderate temperatures and less humidity, which is ideal for exploring the area's outdoor attractions. Spring brings blooming flowers and lush greenery, while autumn showcases beautiful fall foliage, making both periods particularly scenic. You'll find it more comfortable for walking around and enjoying local events without the intense heat of summer or the chill of winter.

For those planning to visit the nearby Babler State Park for hiking or picnics, the milder temperatures of spring and autumn are perfect. Families might especially appreciate these times for outdoor activities, as children can play comfortably without overheating.

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 £69 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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