Winchester Vacations from $495

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The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Country Haven Inn

Country Haven Inn

2.5 out of 5
Price was $511, price is now $495 per person
$495
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip flight included
Chicago (MDW) to Topeka (FOE)
8.6/10 Excellent! (37 reviews)
Room was clean/ no extra amenities/ hallways had a distinct smell that seeped into the room/ friendly staff/

Reviewed on May 19, 2026

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Winchester Hotel Deals

DoubleTree by Hilton Hotel Lawrence

DoubleTree by Hilton Hotel Lawrence

4 out of 5
200 Mcdonald Dr Lawrence KS
$89 nightly
The price is $105 total per night from May 31 to Jun 1
$105 total
May 31 - Jun 1
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
"Very clean facility. Friendly, polite staff."

Reviewed on May 23, 2026

DoubleTree by Hilton Hotel Lawrence
Comfort Inn & Suites Lawrence - University Area

Comfort Inn & Suites Lawrence - University Area

2.5 out of 5
151 Mcdonald Dr Lawrence KS
Fully refundable
$94 nightly
The price is $110 total per night from May 31 to Jun 1
$110 total
May 31 - Jun 1
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
"Room was nice. Clean. Breakfast had good selection. Sausage would have been better if it were browned more. Biscuits and gravy were good."

Reviewed on May 22, 2026

Comfort Inn & Suites Lawrence - University Area
Saint George Hotel

Saint George Hotel

2 out of 5
500 Main St Weston MO
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $104 total per night from May 26 to May 27
$104 total
May 26 - May 27
Total with taxes and fees
9.2/10 Wonderful! (23 reviews)
"We were in town for one night just to enjoy the wineries and bar scene and this place was a perfect fit for my husband and I. The location was great and the room was clean. The off-site parking created a bit of a challenge but nothing that would keep me from booking here again!"

Reviewed on May 23, 2026

Saint George Hotel
See all 108 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.

Find the Best Winchester Vacation Packages

Winchester Essential Information

Language
English
Currency
U.S dollars
Population
540

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Frequently asked questions

How much does a Winchester vacation package cost?
You can pick up a vacation package to this top destination from $495 on Expedia. But how much your vacation to Winchester costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Winchester?
You can typically find lower prices and greater availability in November, December and January. Check out our cheap Winchester vacation packages and you could score some excellent off-season deals.
How many days is enough for Winchester?
Generally, a handful of days is enough to go to the main attractions during your Winchester vacation. However, if you'd like to have time to rest or go on day tours, think about extending your trip.
How to find the best Winchester package deals?
Bagging a cheap Winchester package deal is a breeze with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget, add some filters and see what's available. You can tweak your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to discover the most economical Winchester package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Winchester vacation as a package?
You can enjoy significant savings on your next Winchester retreat by booking a personalized vacation package. Check the "Package" heading, then enter your travel dates and destination to see some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Winchester?
If you've got your Winchester vacation dates finalized, book as early as you can to snap up some terrific deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for quick escapes.
Does Expedia offer Book Now, Pay Later Winchester vacation packages?
If you're like us, you love traveling but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Winchester vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.