Winchester Vacations from $259

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Your Winchester Vacation

History, cuisine, art and more … There's so much to experience with a Winchester vacation package. And with the ability to customize your city getaway, you know it'll be one that's tough to forget. Want to explore? Winchester Speedway, Winchester Golf Club and Historic Shopping & Dining District of Winchester, Indiana are among the leading places to visit during your trip to Winchester. Expedia has what you need to escape your routine. Tailor your vacation to Winchester to suit your style of travel, whatever that may look like.

The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Fourwinds Lakeside Inn & Marina

Fourwinds Lakeside Inn & Marina

3 out of 5
Save 100% on your flight
Price was $415, price is now $259 per person
$259
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
New York (NYC) to Indianapolis (IND)
8.2/10 Very Good! (703 reviews)
Could be a bit better if wifi service was available as sone of us work while away. And corporate should rethink their restaurant prices versus what they offer. Ive been here 2 times and enjoy the place very much, my kid loves it

Reviewed on Aug 12, 2025

InterContinental Indianapolis by IHG

InterContinental Indianapolis by IHG

4 out of 5
Downtown Indianapolis
Save 100% on your flight
Price was $1,270, price is now $882 per person
$882
per person
Oct 23 - Oct 27
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Indianapolis (IND)
9.4/10 Exceptional! (52 reviews)
Really nice hotel!!!

Reviewed on Aug 17, 2025

Hampton Inn Indianapolis Downtown IUPUI

Hampton Inn Indianapolis Downtown IUPUI

2.5 out of 5
Downtown Indianapolis
Price was $712, price is now $526 per person
$526
per person
Oct 23 - Oct 27
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Indianapolis (IND)
8.8/10 Excellent! (657 reviews)
I liked that the property was on the canal and was pretty. It was a busy weekend in Indy, so the room rates were pretty high. Our room was half the size as my sister's room (I think hers was a suite), but our prices for the room were the same. The surroundings were nice. The staff were all very nice, friendly and professional. We would stay there again.

Reviewed on Aug 15, 2025

Homewood Suites by Hilton Indianapolis Downtown IUPUI

Homewood Suites by Hilton Indianapolis Downtown IUPUI

3 out of 5
Downtown Indianapolis
Price was $757, price is now $567 per person
$567
per person
Oct 23 - Oct 27
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Indianapolis (IND)
9.2/10 Wonderful! (558 reviews)
Very friendly & helpful staff.

Reviewed on Aug 15, 2025

Bottleworks Hotel

Bottleworks Hotel

4.5 out of 5
Downtown Indianapolis
Price was $1,212, price is now $912 per person
$912
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Indianapolis (IND)
9.8/10 Exceptional! (1,520 reviews)
Very clean and very aesthetic! One of my favorite hotels. Bunch of food places around for foodies.

Reviewed on Aug 17, 2025

Don't see what you're looking for?
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Discover the most popular places to visit in Winchester

Winchester Speedway

Catch an event at Winchester Speedway during your trip to Winchester.

Winchester Speedway

Winchester Golf Club

Enjoy a round of golf in Winchester at Winchester Golf Club.

Winchester Golf Club

Winchester Hotel Deals

Randolph Inn and Suites

Randolph Inn and Suites

2.5 out of 5
890 E Washington, Winchester, IN
$108 nightly
The price is $121 total per night from Aug 20 to Aug 21
$121 total
Aug 20 - Aug 21
Total includes taxes and fees
8.8/10 Excellent! (230 reviews)
"It was very clean and the staff was very accommodating. It was close to the Walmart for anything that you would need and restaurants."

Reviewed on Jul 20, 2025

Randolph Inn and Suites
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! (177 reviews)
"Our ladies retreat enjoyed our time at the home. The pool was very clean. However the hot tub smelled strongly of chlorine and was a bit of a concern for us. This home is perfect for a large group but the location itself was not as ideal. There is not a lot of options for things to do in the area. ..."

Reviewed on Aug 4, 2025

Get rates
Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
Baymont by Wyndham Richmond I-70

Baymont by Wyndham Richmond I-70

2.5 out of 5
912 Mendleson Dr, Richmond, IN
$76 nightly
The price is $85 total per night from Aug 24 to Aug 25
$85 total
Aug 24 - Aug 25
Total includes taxes and fees
8.2/10 Very Good! (1,005 reviews)
"Our stay was really good,clean,and good service. Would definitely stay there again"

Reviewed on Aug 16, 2025

Baymont by Wyndham Richmond I-70
See all 110 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 $259 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 book a cheap Winchester vacation package, consider traveling in June, July and November. You'll typically find better rates on flights and accommodations during these months — perfect for a budget-friendly getaway.
How many days is enough for Winchester?
Generally, a handful of days is enough to go to the top attractions during your Winchester vacation. But if you want to have time to kick back or go on day tours, consider extending your trip.
Is it worth booking a vacation package to Winchester?
It's no wonder a Winchester vacation is on the must-do list of many travelers. Top attractions like Winchester Speedway are just the beginning of things to keep you busy here.
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.
Does Expedia offer Book Now, Pay Later Winchester vacation packages?
Secure your perfect escape to Winchester with help from our Book Now, Pay Later vacations. There's no need to save up or wait for your next paycheck — we've teamed up with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans let you spread the total cost across 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily budget for your trip and snap up bargains before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.