Winchester Holidays

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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 S$180 per night from 22 Aug to 23 Aug
S$180
22 Aug - 23 Aug
includes taxes & fees
8.4/10 Very Good! (3,950 reviews)
"Passing through from Texas to Pennsylvania we stopped in St. Louis for a little sightseeing. Upon arrival we went to the 360 Rooftop Bar and could see the final few innings of the Cardinals’ game. The next morning we walked to the Gateway Arch and went to the top for a beautiful view of the city. ..."

Reviewed on 15 Aug, 2025

Hyatt Regency St. Louis at The Arch
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 S$177 per night from 29 Aug to 30 Aug
S$177
29 Aug - 30 Aug
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
"Perfect stay."

Reviewed on 13 Aug, 2025

Renaissance St. Louis Airport Hotel
Drury Plaza Hotel St. Louis at the Arch

Drury Plaza Hotel St. Louis at the Arch

3 out of 5
2 South 4th Street, St. Louis, MO
Fully refundableReserve now, pay when you stay
The price is S$204 per night from 2 Sept to 3 Sept
S$204
2 Sept - 3 Sept
includes taxes & fees
9.4/10 Exceptional! (2,956 reviews)
"Excellent hotel in a great location. Right near the Arch. 10 minute (at worst) walk to the stsdium. Staff was super friendly and quite helpful. We really enjoyed happy hour. Good snack food. The afternoon snacks were outstanding."

Reviewed on 17 Aug, 2025

Drury Plaza Hotel St. Louis at the Arch
See all 1,769 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.

Popular places to visit

Forest Park which includes a pond, flowers and modern architecture

Forest Park

Nature, history and cultural institutions come together in one of the United States’ largest urban parks, which buzzes with St. Louis’ dynamic community spirit.

Forest Park

What to do in Winchester

St Louis: City Museum General Admission Ticket

St Louis: City Museum General Admission Ticket

S$29
per adult
96% of travellers recommend
St Louis: City Museum General Admission Ticket
St. Louis: Gateway Ghouls and Hauntings Walking Tour

St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour

S$31
per adult
St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour
Best of St. Louis Small Group Tour w/ Arch & River Cruise

Best of St. Louis Small Group Tour w/ Arch & River Cruise

S$217
per adult
84% of travellers recommend
Best of St. Louis Small Group Tour w/ Arch & River Cruise
See all activities in Winchester

Frequently asked questions

How much does a Winchester holiday package cost?
You can snap up a holiday package to this top destination on Expedia. However, how much your holiday to Winchester costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Winchester?
Travel in the shoulder or low season and you're likely to find cheap Winchester holiday packages. Remember that school holiday periods and local events and festivals can impact prices, so do your research before booking.
How many days is enough for Winchester?
Generally, a handful of days is enough to check out the major attractions during your Winchester holiday. But if you want to have some time to kick back or go on day trips, think about extending your itinerary.
How to find the best Winchester package deals?
Begin your search for a Winchester package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Winchester package deal straight away, just tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Winchester escape off to a flying start.
Is it cheaper to book a Winchester holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component separately. And you'll still enjoy the flexibility to create a personalised Winchester holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Winchester?
If you're planning a spur-of-the-moment Winchester holiday, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Winchester?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Winchester.
  2. Set your budget: Factor in expenses such as transportation, flights and meals when working out how much to save for your trip to Winchester. Then, pick a property that suits your budget, whether that's an affordable option or a more upscale getaway.
  3. Decide how long to go away for: Now that you're more familiar with Winchester, you can figure out the ideal length of your break. Put together a rough plan and allocate enough time to get through everything on your must-do list.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to pick a Winchester holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.