Winchester Holidays from £936

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Your Winchester Holiday

When a fun city break is calling, answer it with a Winchester holiday package. The neighbourhood of Maplewood, which is great for bars and pubs, gift and craft shops and dining, makes a terrific base for your adventures. There's plenty to include on your itinerary during your trip to Winchester, starting with top attractions such as Castlewood State Park and American Kennel Club Museum of the Dog. Your Winchester holiday is just clicks away. Explore hotels, flights and more on Expedia for a getaway that's tailored just for you.

Top Winchester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was £1,209, price is now £936 per person
£936
per person
26 Aug - 30 Aug
found 1 day ago
Return direct flight included
London (LON) to St. Louis (STL)
9.2/10 Wonderful! (1,667 reviews)
I absolutely love the wildwood. Best place to stay near St Louis. I will be staying with them again.

Reviewed on 21 Jun 2026

Moonrise Hotel

Moonrise Hotel

4 out of 5
Delmar Loop
Price was £1,162, price is now £1,024 per person
£1,024
per person
26 Aug - 30 Aug
found 1 day ago
Return direct flight included
London (LON) to St. Louis (STL)
9/10 Wonderful! (1,981 reviews)
Rooftop bar was the icing on the cake after a long night put at a concert. Can also smoke put there iykyk

Reviewed on 20 Jun 2026

Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
Price was £1,247, price is now £1,105 per person
£1,105
per person
26 Aug - 30 Aug
found 1 day ago
Return direct flight included
London (LON) to St. Louis (STL)
8.6/10 Excellent! (1,000 reviews)
The facility is clean, lots of stores and restaurants, arcade & helpful front desk. We never saw housekeeping during our stay, our DND sign was not out, so not sure why they never stopped in. The pool area is closed to kids on the weekend d/t the bar at the outdoor pool and no lifeguard. However, the indoor pool was empty all weekend. It made no sense why the indoor pool area couldn’t be open for families. We had some disappointed kids. I even called ahead to make sure the pool would be open during our stay, and there was no mention of the adult only rule during the weekend. Had we known that, we would’ve booked elsewhere. We tried to make the best of it and bought arcade cards for the kids, and desserts from Copper Whisk which were nice.

Reviewed on 21 Jun 2026

DoubleTree by Hilton Hotel St. Louis - Chesterfield

DoubleTree by Hilton Hotel St. Louis - Chesterfield

4 out of 5
Price was £1,071, price is now £965 per person
£965
per person
26 Aug - 30 Aug
found 1 day ago
Return direct flight included
London (LON) to St. Louis (STL)
8.8/10 Excellent! (1,002 reviews)
Room was clean and comfortable. Breakfast was very good. All staff we came on contact with were kind and helpful.

Reviewed on 21 Jun 2026

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

4 out of 5
Grand Center
Price was £1,077, price is now £980 per person
£980
per person
26 Aug - 30 Aug
found 1 day ago
Return direct flight included
London (LON) to St. Louis (STL)
8.8/10 Excellent! (1,067 reviews)
Very nice place highly recommend! Staff is amazing.

Reviewed on 21 Jun 2026

Winchester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lambert-St. Louis Intl. Airport (STL)
Population
1,550
Max Temp Winter
4ºC
Max Temp Summer
32ºC

Top hotels in Winchester

Hyatt Regency St. Louis at The Arch

Hyatt Regency St. Louis at The Arch

4 out of 5
315 Chestnut St St. Louis MO
Fully refundableReserve now, pay when you stay
The price is £142 per night from 28 Jun to 29 Jun
£142
28 Jun - 29 Jun
includes taxes & fees
8.6/10 Excellent! (4,141 reviews)
"Very nice upscale hotel . Very clean in all areas . Staff were very helpful. Traveled with my husband and two teens. 3 restaurants and a Starbucks on site . Parking was a little spendy but expected . Blankets and sheets were noisy when someone would move sleep positions during the night . I know ..."

Reviewed on 21 Jun 2026

Hyatt Regency St. Louis at The Arch
Clayton Plaza Hotel & Extended Stay

Clayton Plaza Hotel & Extended Stay

3.5 out of 5
7750 Carondelet Avenue St. Louis MO
Fully refundableReserve now, pay when you stay
The price is £88 per night from 12 Jul to 13 Jul
£88
12 Jul - 13 Jul
includes taxes & fees
8.8/10 Excellent! (3,254 reviews)
"Called and requested towels twice - they never brought towels. We had two rooms since we traveled with family and she refused to give me more than 4 towels even though there were 7 of us between 2 rooms. Also, there is a very slick ramp down to the pool area. My mom slipped and fell a hurt her leg. ..."

Reviewed on 21 Jun 2026

Clayton Plaza Hotel & Extended Stay
Renaissance St. Louis Airport Hotel

Renaissance St. Louis Airport Hotel

4 out of 5
9801 Natural Bridge Road St. Louis MO
Fully refundableReserve now, pay when you stay
The price is £127 per night from 3 Jul to 4 Jul
£127
3 Jul - 4 Jul
includes taxes & fees
8.4/10 Very Good! (1,095 reviews)
"Shuttle driver you the airport was fantastic!"

Reviewed on 21 Jun 2026

Renaissance St. Louis Airport Hotel
See all 1,935 properties in Winchester
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.
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Popular places to visit

Gateway Arch

Gateway Arch

Enjoy 360-degree views and learn about the history of St. Louis at this world-famous landmark.

Gateway Arch
Saint Louis is a City and Urban Center is Missouri with the Iconic Arch

Dome at America’s Center

Catch an event at Dome at America’s Center during your trip to St. Louis. Experience the area's acclaimed art galleries and great live music.

Dome at America’s Center

Six Flags St. Louis

Enjoy the rides and games at Six Flags St. Louis and see why people love this theme park in St. Louis. While in this family-friendly area, you can savour the top-notch restaurants.

Six Flags St. Louis

What to do in Winchester

St. Louis: Gateway Ghouls and Hauntings Walking Tour

St. Louis Ghost Tour: Sinister Sins & Shadows

£18
per adult
100% of travellers recommend
St. Louis Ghost Tour: Sinister Sins & Shadows
Lemp Haunted Neighborhood Walking Tour

Lemp Haunted Neighborhood Walking Tour

£19
per adult
84% of travellers recommend
Lemp Haunted Neighborhood Walking Tour
Downtown St. Louis Smartphone Guided Audio Walking Tour App

Downtown St. Louis Smartphone Guided Audio Walking Tour App

£6
per adult
100% of travellers recommend
Downtown St. Louis Smartphone Guided Audio Walking Tour App
See all activities in Winchester

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.