Winchester Vacations

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Find the Best Winchester Vacation Packages

Winchester Hotel Deals

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
Winchester
9.6/10 Exceptional! (167 reviews)
Family gathering
"Each year our family gathers together from 3 states to spend 4 days together. We plan meals, play games, and spend this time making memories that will last a lifetime. This was a perfect location to spend those 4 days"

Reviewed on 31 December 2024

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
Randolph Inn and Suites
Randolph Inn and Suites
2.5 out of 5
890 E Washington, Winchester, IN
Fully refundableReserve now, pay when you stay
The price is AED 397 per night from Apr 5 to Apr 6
AED 397
AED 444 total
includes taxes & fees
5 Apr - 6 Apr
8.8/10 Excellent! (213 reviews)
"Very nice"

Reviewed on 26 December 2024

Randolph Inn and Suites
Baymont by Wyndham Richmond I-70
Baymont by Wyndham Richmond I-70
2.5 out of 5
912 Mendleson Dr, Richmond, IN
Fully refundableReserve now, pay when you stay
The price is AED 238 per night from Apr 6 to Apr 7
AED 238
AED 267 total
includes taxes & fees
6 Apr - 7 Apr
8/10 Very Good! (999 reviews)
"Updated shower door didn’t stay closed"

Reviewed on 26 March 2025

Baymont by Wyndham Richmond I-70
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.

Frequently asked questions

How much does a Winchester vacation package cost?
You’ll find cheap prices on Expedia for your Winchester getaway. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Winchester costs.
What are the cheapest months to go to Winchester?
If you’re hoping to snag a cheap Winchester vacation package, consider visiting in January, February and May. You’ll usually find better prices on flights and hotels during these quieter months — ideal for budget-conscious travelers.
How to find the best Winchester package deals?
Start your search for a Winchester package deal by entering your preferred trip dates and destination under our “Packages” tab. Then select a few filters, like “Property type” and “Amenities,” to tailor the results to your exact needs. 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 right away, simply 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 adventure underway.
Is it cheaper to book a Winchester vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and accommodations individually. Better still, you can personalize your Winchester trip to match your exact needs. Pick 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?
If you have your Winchester travel dates locked in, book early to snap up some incredible deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Winchester?

  1. Choose your dates: The things you plan to do in Winchester and your favorite season can help you decide when to get away.
  2. Set your budget: Consider costs such as flights, transportation and food when working out how much to save for your trip to Winchester. Then, choose a hotel that suits your budget, whether that’s a low-cost stay or a lavish retreat.
  3. Work out your trip length: Think about how long you’d like to spend discovering Winchester. Plan your days so you can get to all the attractions and experiences you’re interested in without rushing.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a customized Winchester vacation package.

Discover the most popular places to visit in Winchester