Hotels in Winchester

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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 .

Hyatt Regency St. Louis at The Arch

Hyatt Regency St. Louis at The Arch
4.0 star property
Downtown St. Louis
8.6 out of 10, Excellent, (4,220 reviews)
Immerse yourself in downtown St. Louis at this riverside hotel near Gateway Arch and Busch Stadium. Enjoy 3 restaurants, 2 bars, and a rooftop terrace with city views. The health club offers workout options after exploring nearby Mississippi River attractions.
$134 nightly
The price is $158
Aug 28 - Aug 29
Total with taxes and fees
Hyatt Regency St. Louis at The Arch

Drury Plaza Hotel St. Louis at the Arch

Drury Plaza Hotel St. Louis at the Arch
3.0 star property
Downtown St. Louis
9.6 out of 10, Exceptional, (3,650 reviews)
Just steps from Gateway Arch and Busch Stadium, this hotel combines comfort with convenience. Enjoy the indoor pool, hot tub, and free breakfast before exploring St. Louis. With subway stations nearby and in-room refrigerators, your city adventure awaits.
$153 nightly
The price is $179
Aug 15 - Aug 16
Total with taxes and fees
Drury Plaza Hotel St. Louis at the Arch

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, (1,516 reviews)
Find unexpected tranquility at this Fenton hotel with dual pools. The quiet atmosphere, convenient location, and free breakfast earn top marks, while nearby Museum of Transportation offers unique exploration. Friendly staff and free parking add value.
$93 nightly
The price is $108
Aug 23 - Aug 24
Total with taxes and fees
Heritage Inn & Suites St. Louis/Fenton, Trademark by Wyndham

Clayton Plaza Hotel & Extended Stay

Clayton Plaza Hotel & Extended Stay
3.5 star property
Clayton
9.0 out of 10, Wonderful, (3,356 reviews)
Steps from Clayton Station, this relaxing hotel offers freshly prepared complimentary breakfast and comfortable rooms. Explore nearby St. Louis Zoo and Washington University, then unwind in the indoor pool after a day of sightseeing.
$92 nightly
The price is $107
Aug 30 - Aug 31
Total with taxes and fees
Clayton Plaza Hotel & Extended Stay

The Wildwood Hotel

The Wildwood Hotel
3.5 star property
Wildwood
9.2 out of 10, Wonderful, (1,684 reviews)
Escape to Wildwood where this inviting hotel offers morning swims in the indoor pool and energizing workouts at the fitness center. Near Six Flags St. Louis and Skid Row, guests love the comfortable beds and helpful staff. Enjoy free WiFi, breakfast, and parking.
$81 nightly
The price is $95
Aug 25 - Aug 26
Total with taxes and fees
The Wildwood Hotel

Drury Plaza Hotel St. Louis Chesterfield

Drury Plaza Hotel St. Louis Chesterfield
3.0 star property
Chesterfield
9.6 out of 10, Exceptional, (1,242 reviews)
This welcoming hotel features both indoor and outdoor pools plus a relaxing hot tub. Enjoy free parking, WiFi, and breakfast before exploring nearby Chesterfield Arts. Business travelers appreciate the fitness center and in-room refrigerators with microwaves.
$130 nightly
The price is $151
Aug 16 - Aug 17
Total with taxes and fees
Drury Plaza Hotel St. Louis Chesterfield

Drury Inn & Suites Southwest St. Louis

Drury Inn & Suites Southwest St. Louis
3.0 star property
Valley Park
9.6 out of 10, Exceptional, (1,010 reviews)
Close to Six Flags St. Louis, this welcoming hotel offers both outdoor and indoor pools, plus a hot tub for evening relaxation. Enjoy complimentary perks including WiFi, parking, and breakfast that guests rave about.
$119 nightly
The price is $139
Aug 16 - Aug 17
Total with taxes and fees
Drury Inn & Suites Southwest St. Louis

River City Casino & Hotel

River City Casino & Hotel
4.0 star property
St. Louis
9.0 out of 10, Wonderful, (1,724 reviews)
Immerse yourself in gaming excitement at this hotel with an upscale steakhouse, 24-hour fitness center, and complimentary parking. Located near Jefferson Barracks Historic Park, guests consistently praise the attentive staff and immaculate accommodations.
$112 nightly
The price is $130
Aug 13 - Aug 14
Total with taxes and fees
River City Casino & Hotel

Pear Tree Inn St. Louis Airport

Pear Tree Inn St. Louis Airport
2.5 star property
St. Ann
9.2 out of 10, Wonderful, (3,147 reviews)
Wake to a complimentary breakfast at this airport-adjacent hotel offering a free shuttle service. Just 10 minutes from Lambert Main Terminal Station, enjoy the seasonal outdoor pool and fitness center after exploring nearby attractions.
$90 nightly
The price is $106
Aug 17 - Aug 18
Total with taxes and fees
Pear Tree Inn St. Louis Airport

Moonrise Hotel

Moonrise Hotel
4.0 star property
Delmar Loop
9.0 out of 10, Wonderful, (2,031 reviews)
Experience boutique comfort near Washington University and Forest Park. Unwind at the rooftop terrace or energize at the 24-hour fitness center after exploring nearby St. Louis Zoo. With 2 bars and exceptional dining, this hotel sits just minutes from Delmar Station.
$195 nightly
The price is $232
Aug 11 - Aug 12
Total with taxes and fees
Moonrise Hotel

Best Western St. Louis-Kirkwood Route 66

Best Western St. Louis-Kirkwood Route 66
3.5 star property
Kirkwood
8.2 out of 10, Very Good, (1,530 reviews)
Just off Route 66, this Kirkwood hotel offers a seasonal outdoor pool and children's splash area. Enjoy free breakfast before exploring nearby Forest Park or dining at the on-site Chili's. Comfortable beds and helpful staff make for a peaceful, convenient stay.
$96 nightly
The price is $113
Aug 30 - Aug 31
Total with taxes and fees
Best Western St. Louis-Kirkwood Route 66

Wingate by Wyndham St. Louis/Fenton Route 66

Wingate by Wyndham St. Louis/Fenton Route 66
3.0 star property
Fenton
7.6 out of 10, Good, (1,327 reviews)
Experience peaceful nights at this Fenton hotel despite its prime location near major roads. Free continental breakfast and parking enhance your stay, while the outdoor pool offers refreshment after exploring nearby Museum of Transportation and shopping areas.
$84 nightly
The price is $97
Aug 31 - Sep 1
Total with taxes and fees
Wingate by Wyndham St. Louis/Fenton Route 66

Live by Loews - St.Louis

Live by Loews - St.Louis
4.0 star property
Downtown St. Louis
9.4 out of 10, Exceptional, (1,296 reviews)
Steps from Busch Stadium and Stadium Station, this St. Louis hotel offers spectacular city views from the rooftop terrace. Dine at Clark & Bourbon restaurant or grab drinks at the acclaimed bar. Gateway Arch and America's Center Convention Complex are within a 15-minute walk.
$159 nightly
The price is $189
Aug 31 - Sep 1
Total with taxes and fees
Live by Loews - St.Louis

Magnolia Hotel St. Louis, a Tribute Portfolio Hotel

Magnolia Hotel St. Louis, a Tribute Portfolio Hotel
4.0 star property
Downtown St. Louis
8.8 out of 10, Excellent, (1,360 reviews)
Step into historic elegance at this Baroque hotel, just minutes from Gateway Arch and America's Center. Enjoy American cuisine at Robie's restaurant or unwind at the bar after a 24-hour fitness center workout. 8th and Pine Station is a convenient 3-minute stroll away.
$105 nightly
The price is $125
Aug 30 - Aug 31
Total with taxes and fees
Magnolia Hotel St. Louis, a Tribute Portfolio Hotel

Hyatt Place St. Louis/Chesterfield

Hyatt Place St. Louis/Chesterfield
3.0 star property
Chesterfield
9.6 out of 10, Exceptional, (1,008 reviews)
Situated close to Chesterfield Arts and Amphitheater, this hotel offers an indoor pool and complimentary breakfast. Enjoy American cuisine at The Placery restaurant or unwind at the bar after using the 24-hour fitness center.
$130 nightly
The price is $150
Aug 30 - Aug 31
Total with taxes and fees
Hyatt Place St. Louis/Chesterfield

Forest Park Hotel by MDR

Forest Park Hotel by MDR
3.0 star property
The Hill
7.4 out of 10, Good, (1,661 reviews)
Discover comfort just minutes from Forest Park and Barnes Jewish Hospital. This hotel offers free WiFi and parking, with hiking trails nearby. St. Louis Union Station and Gateway Arch are a short drive away, while helpful staff ensure a pleasant experience.
$86 nightly
The price is $101
Sep 9 - Sep 10
Total with taxes and fees
Forest Park Hotel by MDR

Pear Tree Inn St. Louis Near Union Station

Pear Tree Inn St. Louis Near Union Station
3.0 star property
Downtown West
8.8 out of 10, Excellent, (2,131 reviews)
Dive into city adventures from this centrally-located hotel with an indoor pool and hot tub. Just a 15-minute walk from St. Louis Union Station and near Gateway Arch, you'll enjoy free breakfast, WiFi, and parking. Rooms include refrigerators and microwaves.
$122 nightly
The price is $143
Aug 16 - Aug 17
Total with taxes and fees
Pear Tree Inn St. Louis Near Union Station

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, (1,020 reviews)
$140 nightly
The price is $163
Aug 30 - Aug 31
Total with taxes and fees
Drury Plaza Hotel St. Louis Creve Coeur

Hampton Inn St. Louis/Chesterfield

Hampton Inn St. Louis/Chesterfield
3.5 star property
Chesterfield
8.6 out of 10, Excellent, (1,003 reviews)
Enjoy a tranquil stay at this Chesterfield hotel with an indoor pool and fitness center. Located near Hollywood Casino Amphitheatre, you'll find easy access to dining and shopping. Guests love the complimentary breakfast, helpful staff, and convenient free parking.
$100 nightly
The price is $100
Aug 31 - Sep 1
Total with taxes and fees
Hampton Inn St. Louis/Chesterfield

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton
4.0 star property
Grand Center
9.0 out of 10, Wonderful, (1,119 reviews)
Experience St. Louis's vibrant culture at this hotel near Grand Station, with the Gateway Arch nearby. Enjoy artistic spaces, on-site dining at Commonwealth, and a trendy bar after shows at the adjacent Fox Theater.
$91 nightly
The price is $107
Aug 17 - Aug 18
Total with taxes and fees
Angad Arts Hotel St. Louis, Tapestry Collection by Hilton
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.

Check out reviews of Winchester hotels guests love

Frequently asked questions

How much does a hotel room cost in Winchester?
You can find top hotels in Winchester from $95 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?
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.

Find out more about Winchester

Unleash Your Thrill-Seeking Spirit in Winchester's Enchanting Playground

Nestled in the heart of Missouri, Winchester is a hidden gem for adventure seekers and families alike. Known for its thrilling theme park, the area offers exhilarating rides and attractions that delight visitors of all ages. Explore the lush landscapes surrounding the Winchester Country Club for a round of golf or relax at charming hotels and suites near the university. With its vibrant community spirit and blend of fun and relaxation, Winchester invites travelers to create unforgettable memories in this delightful destination. Experience the perfect mix of excitement and tranquility in this captivating Missouri locale.

Discover great hotels near Winchester

Winchester, Missouri offers a range of hotel accommodations from comfortable budget options to more upscale stays. Guests can find cozy rooms and spacious suites, often featuring essential amenities. Room rates vary, making it easy to find something that fits your budget. Enjoy convenient access to local attractions and scenic landscapes during your stay. Here are some of the best hotels near Winchester that our travelers love:

  1. Spark by Hilton St. Louis SouthwestOpens in a new window: This budget-friendly hotel offers a welcoming atmosphere for diverse travelers. Its convenient location and comfortable accommodations make it an ideal choice for those seeking a relaxing getaway. The property features pet-friendly policies, allowing for a more inclusive experience. Guests appreciate the clean and quiet environment, along with courteous staff who ensure a pleasant stay. The hotel provides essential amenities, including a satisfying breakfast, creating a cozy space for all types of travelers.
  2. Marriott St. Louis WestOpens in a new window: As a 3.5-star hotel located in the vibrant city center, Marriott St. Louis West provides a lively urban escape for leisure travelers. The impressive guest rating of 8.4 reflects its appealing offerings, including modern accommodations and a central location that allows easy access to local attractions. With a focus on comfort and quality, the hotel ensures that visitors enjoy a memorable experience while exploring the city’s highlights.
  3. Drury Inn & Suites Southwest St. LouisOpens in a new window: This 3.0-star hotel shines with its exceptional guest rating of 9.6, making it a top choice for travelers seeking a remarkable stay. Drury Inn & Suites Southwest St. Louis boasts a variety of amenities that enhance the guest experience, such as complimentary cribs and a relaxing hot tub. Its inviting atmosphere and attention to cleanliness create a delightful haven for leisure guests. The delightful breakfast and evening food options further elevate the overall experience, ensuring a well-rounded and enjoyable stay.

Where to stay near Winchester

Staying in Maryland Heights, Chesterfield, and Fenton offers great options for visiting Winchester, Missouri. Maryland Heights is known for its lively atmosphere and dining options. Chesterfield excels in shopping and entertainment, while Fenton is ideal for sports enthusiasts. For first-time visitors, Chesterfield is best suited, providing easy access to amenities and attractions.

  1. ChesterfieldOpens in a new window: Chesterfield is a fantastic place to stay if you're looking for a vibrant shopping scene. With a variety of retail options, from local boutiques to major brands, it’s a shopper's paradise. The area also boasts beautiful parks and recreational spaces, perfect for outdoor activities like hiking and picnicking. For a taste of local culture, check out the nearby theaters and galleries that frequently host events and exhibitions. With its family-friendly atmosphere and access to dining options, Chesterfield is an ideal base for travelers wanting to explore the St. Louis area.
  2. Maryland HeightsOpens in a new window: Maryland Heights offers a convenient and lively spot for visitors, especially those interested in enjoying cultural attractions. The area is home to several theaters and performance venues, making it easy to catch a show or concert. You’ll also find plenty of parks for leisurely strolls or outdoor games, along with recreational facilities. Plus, its proximity to the Missouri River provides opportunities for scenic views and outdoor activities. Maryland Heights balances urban convenience with green spaces, making it appealing for both relaxation and exploration.
  3. FentonOpens in a new window: Fenton is a charming community known for its sports facilities, making it a great choice for active travelers. With numerous parks and fields, it’s perfect for soccer enthusiasts and families looking to enjoy a day outdoors. Additionally, the area features a variety of shopping options, from local stores to larger retail chains. Fenton’s friendly atmosphere and small-town vibe give travelers a chance to experience local life while still having easy access to the excitement of nearby cities.

Things to do in Winchester

Winchester offers travelers a delightful mix of charming old town vibes and stunning natural landscapes. Explore lush parks, serene lakes, and scenic trails perfect for hiking. Enjoy thrilling activities like amusement parks and arcade zones, or unwind with live music and theatrical performances. It's a vibrant destination brimming with fun!

  • Gateway ArchOpens in a new window – Stand beneath this iconic monument, a symbol of American westward expansion. Climb to the top for breathtaking views of the St. Louis skyline and the Mississippi River, making it a must-see for any traveler in the area.
  • Center of Creative ArtsOpens in a new window – Dive into a world of artistic expression at this vibrant arts center. Enjoy a variety of performances, workshops, and exhibitions that showcase local talent and creativity, perfect for those looking to experience the arts scene.
  • Route 66 State ParkOpens in a new window – Take a leisurely stroll or bike ride along this historic route. The park offers scenic views and rich history, making it an excellent spot for outdoor activities while you soak in the nostalgia of America’s famed highway.
  • Kirkwood ParkOpens in a new window – Explore the expansive green space of Kirkwood Park, where you can enjoy picnicking, walking trails, and playgrounds. This urban park is ideal for families wanting to relax and play in a beautiful setting.
  • Westport PlazaOpens in a new window – Discover a lively neighborhood filled with shops, restaurants, and entertainment options. Whether you’re in the mood for a meal or some retail therapy, Westport Plaza offers a vibrant atmosphere to unwind and enjoy your day.

4 tips for savvy savings when booking a hotel in Winchester

  1. Book for the cheapest times: The most affordable time to visit Winchester is during January, February, and December, when hotel prices are lower. To fully appreciate the city's key historical landmarks and cultural attractions, it's best to plan for at least a 2 to 3-day stay. This budget-friendly timeframe allows you to explore significant sites that offer great value for money and immerse yourself in Winchester's rich history. Plus, with the possibility that prices might drop during these months, it's an excellent opportunity for travelers on a budget.
  2. Look for last-minute deals on Hotels.com: For travelers seeking options in Winchester, exploring DealsOpens in a new window and Last-Minute DealsOpens in a new window can lead to potential discounts on accommodations close to your travel date. By checking the respective sections on Hotels.com, you may discover competitive rates. Additionally, enabling notifications can keep you informed about flash sales and special promotions. The Smart ShoppingOpens in a new window feature available through the app allows you to compare hotel prices and amenities, helping you to make informed choices. With these tools, you're more likely to find our best options for a memorable getaway.
  3. Be flexible with dates: Prices can fluctuate based on factors like the hotel's location, star rating, and the time of year, so being flexible with your travel dates may help you find savings on your stay in a Winchester hotel. For travelers seeking something special, boutique hotels often provide a more personalized experience and may offer better value. When you book through Hotels.com, we’ll let you know if the price for your chosen dates is above or below the average. If the price is on the higher end, we’ll suggest alternative dates that could help you find a better deal.
  4. Consider your location: Staying near major attractions or downtown areas can be convenient, but it often comes with a higher price tag. If you're looking for more budget-friendly options, consider hotels in neighborhoods that are a bit farther out, where prices are usually more likely to be affordable while still providing decent access to the sites you want to see. You might also want to check out independent hotels located further away, as they can offer a more authentic and wallet-friendly experience.

Best time to go to Winchester

Winchester experiences its lowest average temperature in January, at 32.2°F (0.1°C), while July is the hottest month, with an average temperature of 79.0°F (26.1°C). May is usually the wettest month. June to August are the peak travel months in Winchester, attracting a higher number of tourists. During this peak period, the weather is mostly sunny, accompanied by light rainfall. On the other hand, January, February, and December tend to be quieter times to visit, marked by light rainfall and mostly sunny to mostly cloudy conditions.

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