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 Rp2.238.084 per night from 31 Jul to 1 Aug
Rp2.238.084
Rp2.639.350 total
31 Jul - 1 Aug
includes taxes & fees
8.4/10 Very Good! (3,829 reviews)
"Just loved it, great value"

Reviewed on 10 Jul 2025

Hyatt Regency St. Louis at The Arch
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 Rp2.270.358 per night from 17 Jul to 18 Jul
Rp2.270.358
Rp2.654.707 total
17 Jul - 18 Jul
includes taxes & fees
9.4/10 Exceptional! (2,848 reviews)
"This hotel is literally across the street from the Arch. The extra couple of dollars a night was worth a river/arch view. It was also blocks from Busch Stadium. Breakfast each morning & dinner at night each night was excellent too"

Reviewed on 12 Jul 2025

Drury Plaza Hotel St. Louis at the Arch
The Arch Convention Hotel
The Arch Convention Hotel
3.5 out of 5
811 N 9th Street, St. Louis, MO
Fully refundable
The price is Rp1.833.445 per night from 15 Jul to 16 Jul
Rp1.833.445
Rp2.144.020 total
15 Jul - 16 Jul
includes taxes & fees
6.8/10 (1,010 reviews)
"Сам отель и комната были довольно комфортные. Обслуживающий персоонал работал отлично. Сначала мне дали комнату на 5 этаже, но там было жарко. Тогда мне поменяли комнату на 4 этаж, где было прохладнее. Единственное, что мне не понравилось - старые слабые кодиционеры."

Reviewed on 11 Jul 2025

The Arch Convention Hotel
See all 1,800 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

5/5(3 reviews)

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

Hollywood Casino

Why not roll the dice with a visit to Hollywood Casino during your visit to Maryland Heights? Visit the casinos and top-notch restaurants in this family-friendly area.

Hollywood Casino

What to do in Winchester

St Louis: City Museum General Admission Ticket

St Louis: City Museum General Admission Ticket

Rp360.825
per adult
94% of travellers recommend
St Louis: City Museum General Admission Ticket
St. Louis Arch Walking Tour and Entrance Ticket

St. Louis Arch Walking Tour and Entrance Ticket

Rp809.588
per adult
St. Louis Arch Walking Tour and Entrance Ticket
St Louis art museum

St. Louis Narrated Trolley Tour

Rp485.850
per adult
92% of travellers recommend
St. Louis Narrated Trolley Tour
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.