Winchester Vacations from $191

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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.
Catalina Airport Motel

Catalina Airport Motel

2 out of 5
Price was $231, price is now $191 per person
$191
per person
May 27 - May 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Indianapolis (IND)
4.6/10 (52 reviews)
$20 cash deposit for room key

Reviewed on Aug 26, 2025

Omni Severin Hotel

Omni Severin Hotel

4 out of 5
Downtown Indianapolis
Price was $533, price is now $420 per person
$420
per person
May 28 - May 31
found 21 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Indianapolis (IND)
9.4/10 Exceptional! (865 reviews)
I really enjoyed my stay at the Omni. The hotel is aesthetically pleasing (great for pictures) and very clean. The staff was wonderful and friendly. The food I had at 8 Notch, which is a breakfast/ lunch style restaurant downstairs, was good. I will definitely stay here in the future.

Reviewed on Apr 1, 2026

Days Inn by Wyndham Muncie -Ball State University

Days Inn by Wyndham Muncie -Ball State University

2 out of 5
Price was $478, price is now $379 per person
$379
per person
May 1 - May 3
found 1 day ago
Roundtrip flight included
New York (LGA) to Indianapolis (IND)
6.8/10 (908 reviews)
The room was nice and clean. Breakfast average.

Reviewed on Feb 15, 2026

Comfort Inn & Suites Indianapolis Northwest - College Park

Comfort Inn & Suites Indianapolis Northwest - College Park

2.5 out of 5
College Park
Price was $356, price is now $284 per person
$284
per person
May 1 - May 3
found 23 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Indianapolis (IND)
7.4/10 Good! (355 reviews)
This place was so good

Reviewed on Mar 25, 2026

Bottleworks Hotel

Bottleworks Hotel

4.5 out of 5
Downtown Indianapolis
Price was $596, price is now $479 per person
$479
per person
May 1 - May 3
found 23 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Indianapolis (IND)
9.8/10 Exceptional! (1,844 reviews)
Awesome boutique hotel. Close to shopping, amazing food,wonderful spa.

Reviewed on Mar 30, 2026

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Discover the most popular places to visit in Winchester

Winchester Speedway

4/5(16 reviews)

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

Winchester Speedway

Winchester Golf Club

3.5/5(4 reviews)

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

Winchester Golf Club

Winchester Hotel Deals

Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA

Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA

Winchester IN
9.8/10 Exceptional! (200 reviews)
We have rented large reunion places before. This one looks better online than it was in person. Functionally everything worked, but the decor and furniture were highly dated, hence four stars instead of five. The cleanliness was OK except in the basement, which was very dusty. We had great conversations ...

Reviewed on Mar 8, 2026

Get rates
Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA
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
$108 nightly
The price is $121 total per night from Apr 2 to Apr 3
$121 total
Apr 2 - Apr 3
Total with taxes and fees
9/10 Wonderful! (253 reviews)
There are 2 properties, a motel and a hotel. This is NOT clear when you are making a reservation thru Expedia. The motel is older. The beds are super low. The shower is small. You have to drive to the hotel to eat breakfast and check in/out. The breakfast was good with hot items. The pool was closed ...

Reviewed on Mar 30, 2026

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
$69 nightly
The price is $77 total per night from Apr 5 to Apr 6
$77 total
Apr 5 - Apr 6
Total with taxes and fees
8.4/10 Very Good! (1,005 reviews)
Looking from the outside, I was not impressed but my room was clean, the air conditioner kept the room cool and the breakfast was excellent, especially for the price I paid. I would definitely stay here again.

Reviewed on Mar 31, 2026

Baymont by Wyndham Richmond I-70
See all 137 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
4,800
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Winchester Speedway, Winchester Golf Club and Historic Shopping & Dining District of Winchester, Indiana

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Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices from $191 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.