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Our top choices for Winchester hotels

1. 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
$130 nightly
The price is $151
Nov 19 - Nov 20
Total with taxes and fees
Drury Plaza Hotel St. Louis Chesterfield

2. The Wildwood Hotel

The Wildwood Hotel
3.5 star property
Wildwood
9.2 out of 10, Wonderful, (1,682 reviews)
"Clean, quiet, great continental breakfast, and close to several places to eat."
United States
Lori
$88 nightly
The price is $103
Dec 15 - Dec 16
Total with taxes and fees
The Wildwood Hotel

3. Sonesta ES Suites St. Louis - Chesterfield

Sonesta ES Suites St. Louis - Chesterfield
3.0 star property
Chesterfield
8.0 out of 10, Very good, (1,069 reviews)
"Breakfast was great"
United States
Shuntichia
$83 nightly
The price is $97
Nov 15 - Nov 16
Total with taxes and fees
Sonesta ES Suites St. Louis - Chesterfield

4. 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, (1,654 reviews)
"Good breakfast and hot tub was nice."
United States
michael
$89 nightly
The price is $103
Nov 15 - Nov 16
Total with taxes and fees
Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

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, (1,000 reviews)
"The bed was very comfortable."
United States
Ann
$87 nightly
The price is $100
Dec 13 - Dec 14
Total with taxes and fees
Holiday Inn Express & Suites St. Louis West - Fenton by IHG

6. Drury Inn & Suites Southwest St. Louis

Drury Inn & Suites Southwest St. Louis
3.0 star property
Valley Park
9.6 out of 10, Exceptional, (1,012 reviews)
"Great stay for family reunion. Staff was friendly and facilities were perfect."
United States
Crystal
$119 nightly
The price is $139
Nov 22 - Nov 23
Total with taxes and fees
Drury Inn & Suites Southwest St. Louis

7. Hyatt Place St. Louis/Chesterfield

Hyatt Place St. Louis/Chesterfield
3.0 star property
Chesterfield
9.6 out of 10, Exceptional, (1,002 reviews)
"Very nice hotel and lovely room"
United States
Karin
$126 nightly
The price is $146
Dec 2 - Dec 3
Total with taxes and fees
Hyatt Place St. Louis/Chesterfield

8. Best Western Plus Fenton

Best Western Plus Fenton
2.5 star property
Fenton
9.0 out of 10, Wonderful, (485 reviews)
"This is 2 Stars hotel. Everything is very basic."
United States
rita
$93 nightly
The price is $107
Nov 16 - Nov 17
Total with taxes and fees
Best Western Plus Fenton

9. 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
$107 nightly
The price is $124
Nov 29 - Nov 30
Total with taxes and fees
Fairfield Inn & Suites by Marriott St. Louis Chesterfield

10. 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
$111 nightly
The price is $129
Nov 28 - Nov 29
Total with taxes and fees
DoubleTree by Hilton Hotel St. Louis - Chesterfield

11. Hampton Inn St. Louis/Chesterfield

Hampton Inn St. Louis/Chesterfield
3.5 star property
Chesterfield
8.6 out of 10, Excellent, (1,001 reviews)
"Everything was spotlessly clean, staff were amazing and breakfast was exceptional! Will definitely be starting again!"
United States
Susan
$105 nightly
The price is $122
Nov 23 - Nov 24
Total with taxes and fees
Hampton Inn St. Louis/Chesterfield

12. 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, (1,005 reviews)
"Great place!"
United States
Edward
$94 nightly
The price is $110
Nov 15 - Nov 16
Total with taxes and fees
La Quinta Inn & Suites by Wyndham St Louis Route 66

13. 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
$107 nightly
The price is $124
Nov 22 - Nov 23
Total with taxes and fees
Marriott St. Louis West

14. 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
$106 nightly
The price is $124
Nov 29 - Nov 30
Total with taxes and fees
Hilton Garden Inn Chesterfield

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
$118 nightly
The price is $137
Nov 27 - Nov 28
Total with taxes and fees
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, (1,001 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
$114 nightly
The price is $133
Nov 22 - Nov 23
Total with taxes and fees
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, (1,214 reviews)
"Clean rooms good breakfast."
United States
Susan
$71 nightly
The price is $82
Nov 22 - Nov 23
Total with taxes and fees
Best Western St. Louis Inn

18. 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, (1,164 reviews)
"Rooms are very clean, the staff is friendly and the location is great. We enjoyed are stay."
United States
Matthew
$81 nightly
The price is $95
Dec 6 - Dec 7
Total with taxes and fees
Sleep Inn & Suites O'Fallon MO - Technology Drive

19. Drury Plaza Hotel St. Louis Creve Coeur

Drury Plaza Hotel St. Louis Creve Coeur
3.0 star property
Creve Coeur
9.4 out of 10, Exceptional, (1,000 reviews)
"Room was clean Breakfast was great and the staff was very friendly"
United States
Shannon
$123 nightly
The price is $143
Dec 13 - Dec 14
Total with taxes and fees
Drury Plaza Hotel St. Louis Creve Coeur

20. Pear Tree Inn St. Louis Arnold

Pear Tree Inn St. Louis Arnold
2.5 star property
Arnold
9.4 out of 10, Exceptional, (1,003 reviews)
"Great Place to stay!"
United States
Charlotte
$90 nightly
The price is $104
Nov 19 - Nov 20
Total with taxes and fees
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.

Hotels recommended for families in Winchester

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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 $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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