Winchester Vacations from $267

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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.
Norwood Inn & Suites Indianapolis

Norwood Inn & Suites Indianapolis

2.5 out of 5
Price was $346, price is now $267 per person
$267
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip flight included
New York (LGA) to Indianapolis (IND)
4.4/10 (457 reviews)
not good , window was open , change room, towel was not there

Reviewed on Nov 29, 2025

Bottleworks Hotel

Bottleworks Hotel

4.5 out of 5
Downtown Indianapolis
Save 100% on your flight
Price was $623, price is now $434 per person
$434
per person
Feb 18 - Feb 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Indianapolis (IND)
9.8/10 Exceptional! (1,664 reviews)
Beautiful space and wonderful staff with delicious food nearby.

Reviewed on Dec 16, 2025

Fairfield Inn & Suites by Marriott Indianapolis Carmel

Fairfield Inn & Suites by Marriott Indianapolis Carmel

2.5 out of 5
Price was $596, price is now $434 per person
$434
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip flight included
New York (LGA) to Indianapolis (IND)
9.6/10 Exceptional! (568 reviews)
The breakfast is excellent.

Reviewed on Dec 5, 2025

Ironworks Hotel Indy

Ironworks Hotel Indy

4 out of 5
Save 100% on your flight
Price was $837, price is now $650 per person
$650
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip flight included
New York (LGA) to Indianapolis (IND)
9.8/10 Exceptional! (1,698 reviews)
From the moment we arrived, this hotel exceeded every expectation. The check-in process was seamless and welcoming, and the staff made me feel genuinely valued throughout my stay. The room was immaculate, beautifully designed, and incredibly comfortable. The bed felt luxurious, the linens were crisp, and the attention to detail—from the lighting to the amenities—made it easy to relax and feel at home. The hotel’s facilities were equally impressive. Whether it was the gorgeous common areas, the well-equipped fitness center, everything was maintained to the highest standard. Breakfast was a highlight: fresh, varied, and delicious, with options to suit every preference. It’s rare to find a place where excellence feels so effortless. I would not hesitate to return and wholeheartedly recommend this hotel to anyone looking for quality, and exceptional hospitality. A truly memorable stay.

Reviewed on Dec 17, 2025

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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

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
9.6/10 Exceptional! (183 reviews)
This was a beautiful home was enjoyed by all. The amenities are great, Walmart is right around the corner, the pool was warm and Ted was very welcoming. We were disappointed to learn that the hot tub had been closed early due to cold weather, but that don’t stop us from having a great time! We would ...

Reviewed on Dec 16, 2025

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 Dec 19 to Dec 20
$121 total
Dec 19 - Dec 20
Total with taxes and fees
8.8/10 Excellent! (243 reviews)
Breakfast was good.the staff very friendly and the other hotel guest very friendly

Reviewed on Oct 28, 2025

Randolph Inn and Suites
Days Inn by Wyndham Muncie -Ball State University

Days Inn by Wyndham Muncie -Ball State University

2 out of 5
3509 N Everbrook Ln Muncie IN
Fully refundableReserve now, pay when you stay
$65 nightly
The price is $73 total per night from Dec 21 to Dec 22
$73 total
Dec 21 - Dec 22
Total with taxes and fees
6.6/10 (887 reviews)
Good price, clean. No elevator, but was on 1st floor, but still weird.

Reviewed on Nov 29, 2025

Days Inn by Wyndham Muncie -Ball State University
See all 133 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 $267 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.