Winchester Vacations from $280

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The Latest Winchester vacation packages

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

The Wildwood Hotel

3.5 out of 5
Price was $425, price is now $280 per person
$280
per person
Nov 15 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,562 reviews)
Very quiet, nice area. Walkable to restaurants and shops. The staff was extremely welcoming. This is a beautiful facility and is even pet friendly. I would highly recommend this hotel if you need to stay in this area.

Reviewed on Aug 29, 2025

The Principal Hotel

The Principal Hotel

3.5 out of 5
Price was $608, price is now $429 per person
$429
per person
Oct 30 - Nov 3
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to St. Louis (STL)
9.8/10 Exceptional! (120 reviews)
Overall was the best stay we have had with any one. The only downside would be no hot breakfast unless you went to the restaurant on location. Staff was great and so helpful when we needed anything for the room.

Reviewed on Aug 18, 2025

White House at Grand Central

White House at Grand Central

4 out of 5
Grand Center
Price was $642, price is now $477 per person
$477
per person
Oct 30 - Nov 3
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to St. Louis (STL)
8.6/10 Excellent! (116 reviews)
It was very clean and nicely decorated. The house is a cool old building. The AC worked great (important, as it was super muggy outside.) I was only there for a couple nights but I think it would have worked well for a longer stay.

Reviewed on Jul 9, 2025

Home2 Suites by Hilton St. Louis Downtown

Home2 Suites by Hilton St. Louis Downtown

3 out of 5
Downtown West
Price was $530, price is now $404 per person
$404
per person
Oct 30 - Nov 3
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to St. Louis (STL)
8/10 Very Good! (498 reviews)
Loved the historical property and surrounding historical activities.

Reviewed on Aug 23, 2025

Courtyard by Marriott St. Louis Downtown/Convention Center

Courtyard by Marriott St. Louis Downtown/Convention Center

3 out of 5
Downtown St. Louis
Price was $564, price is now $437 per person
$437
per person
Oct 30 - Nov 3
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to St. Louis (STL)
9/10 Wonderful! (1,005 reviews)
Clean, friendly staff. Would stay here again!

Reviewed on Aug 26, 2025

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Winchester Hotel Deals

Sleep Inn & Suites

Sleep Inn & Suites

2.5 out of 5
2401 Holliday Ln, Jacksonville, IL
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $88 total per night from Sep 7 to Sep 8
$88 total
Sep 7 - Sep 8
Total with taxes and fees
Sleep Inn & Suites
Best Western Jacksonville Inn

Best Western Jacksonville Inn

2.5 out of 5
1709 W Morton Ave, Jacksonville, IL
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $85 total per night from Aug 31 to Sep 1
$85 total
Aug 31 - Sep 1
Total with taxes and fees
Best Western Jacksonville Inn
Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

2 out of 5
1003 W Morton Ave, Jacksonville, IL
Fully refundableReserve now, pay when you stay
$55 nightly
The price is $63 total per night from Sep 7 to Sep 8
$63 total
Sep 7 - Sep 8
Total with taxes and fees
Super 8 by Wyndham Jacksonville
See all 43 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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Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices from $280 on Expedia for your Winchester getaway. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Winchester costs.
What are the cheapest months to go to Winchester?
You can usually find reduced prices and better availability in November, December and January. Take a look at our cheap Winchester vacation packages and you could land some great off-season deals.
How many days is enough for Winchester?
The ideal duration of your Winchester vacation depends on what you'd like to see and do. Typically, a handful of days to a week will give you enough time to tick off all the top attractions and explore some hidden treasures along the way.
How to find the best Winchester package deals?
Use Expedia's handy filters to find some terrific Winchester package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Winchester package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Winchester vacation as a package?
An Expedia vacation package could land you great savings when compared to booking hotels and flights individually. Better still, you can personalize your Winchester trip to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Winchester?
Secure fantastic discounts by reserving your flights in advance with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment Winchester adventure.
Does Expedia offer Book Now, Pay Later Winchester vacation packages?
Your Winchester break should be an escape from your busy life, not a source of money worries. So to allow you a bit more flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.