Deals on vacations and trips to Winchester

Save when you book Winchester, IN package deals

Choose two or more items and save on your trip:

Winchester flight + hotel vacation packages

Ironworks Hotel Indy

Ironworks Hotel Indy

4 out of 5
per person
Jun 21 - Jun 23
Roundtrip flight included
Austin (AUS) to Indianapolis (IND)
This smoke-free hotel's 4 restaurants, 3 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Free self parking, a coffee shop, and dry cleaning are also offered.
Motel 6 Fishers, IN - Indianapolis

Motel 6 Fishers, IN - Indianapolis

2 out of 5
per person
May 25 - May 27
Roundtrip non-stop flight included
Austin (AUS) to Indianapolis (IND)
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.
Studio 6 Fishers, IN - Indianapolis

Studio 6 Fishers, IN - Indianapolis

2 out of 5
per person
May 25 - May 27
Roundtrip non-stop flight included
Austin (AUS) to Indianapolis (IND)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A snack bar/deli and laundry facilities are also provided.
JW Marriott Indianapolis

JW Marriott Indianapolis

4 out of 5
Downtown Indianapolis
per person
May 31 - Jun 3
Roundtrip flight included
Austin (AUS) to Indianapolis (IND)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and express check-in are also offered.
Sonesta Select Indianapolis Carmel

Sonesta Select Indianapolis Carmel

3 out of 5
per person
Jun 21 - Jun 23
Roundtrip flight included
Austin (AUS) to Indianapolis (IND)
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a coffee shop, and a lobby fireplace are also offered.
Prices and availability subject to change. Additional terms may apply.

Top Winchester hotels deals

Randolph Inn and Suites

Randolph Inn and Suites

2.5 out of 5
890 E Washington, Winchester, IN
Free Cancellation
Reserve now, pay when you stay
The price is $150 per night
$150
per night
Apr 19 - Apr 20
This hotel features an indoor pool and a gym. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A business center, a terrace, and laundry facilities are also on offer.
Baymont by Wyndham Muncie Near Ball State University

Baymont by Wyndham Muncie Near Ball State University

2.5 out of 5
3400 North Chadam Lane, Muncie, IN
Free Cancellation
Reserve now, pay when you stay
The price is $60 per night
$60
per night
Apr 21 - Apr 22
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 2 conference rooms, 24-hour business center, and express check-in. Enjoy the gym and conveniences like a 24-hour front desk and barbecue grills.
Baymont by Wyndham Richmond I-70

Baymont by Wyndham Richmond I-70

2.5 out of 5
912 Mendleson Dr, Richmond, IN
Free Cancellation
Reserve now, pay when you stay
The price is $71 per night
$71
per night
May 12 - May 13
An indoor pool, free self parking, and laundry facilities are featured at this inn. Guests will appreciate free perks like self-serve breakfast and WiFi in public areas. A business center, dry cleaning, and free newspapers are also on offer.
Courtyard Muncie at Horizon Convention Center

Courtyard Muncie at Horizon Convention Center

3 out of 5
601 S High St, Muncie, IN
Free Cancellation
Reserve now, pay when you stay
The price is $103 per night
$103
per night
May 5 - May 6
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, a coffee shop, and a grocery/convenience store are also offered.
Comfort Suites

Comfort Suites

2.5 out of 5
421 Commerce Road, Richmond, IN
Free Cancellation
Reserve now, pay when you stay
The price is $102 per night
$102
per night
May 19 - May 20
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Quality Inn and Conference Center

Quality Inn and Conference Center

2.5 out of 5
5501 National Rd E, Richmond, IN
Free Cancellation
Reserve now, pay when you stay
The price is $58 per night
$58
per night
May 12 - May 13
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Don't see what you're looking for?
See all available properties in Winchester
View all properties
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.

Popular places to visit

Image for Winchester Speedway

Winchester Speedway

4/5(16 reviews)

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

Winchester Speedway
Image for Winchester Golf Club

Winchester Golf Club

3.5/5(4 reviews)

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

Winchester Golf Club
Image for Historic Shopping & Dining District of Winchester, Indiana

Historic Shopping & Dining District of Winchester, Indiana

4.5/5(2 reviews)

You can find out about the history of Winchester with a trip to Historic Shopping & Dining District of Winchester, Indiana.

Historic Shopping & Dining District of Winchester, Indiana

Frequently asked questions

How much are vacation packages to Winchester?
Starting at just $408, hotel and flight packages are the perfect way to make your travel budget stretch further. Winchester, here you come!
How long should my Winchester vacation be?
There aren’t any hard and fast rules for how long you should spend in Winchester, but the majority of travelers opt to stay for around 2 nights. Got some flexibility with your departure date? Consider booking a few extra nights. Then you’ll have plenty of time to discover the area’s hidden gems as well.
Where can I get the best vacation package deals for Winchester?
Find your dream escape at Travelocity. With access to 400 air carriers and at least 1,000,000 hotels all over the world, finding the perfect Winchester package deal couldn’t be easier.
Why should I book my Winchester vacation package via Travelocity?
Travel is all about making cherished memories and forgetting all your worries — which is why we have a team of experts on hand around-the-clock should you need them. On top of that, our Price Match Guarantee ensures you’ll always get the best deal available on our huge range of vacation destinations. So what are you waiting for? There’s no time like the present to secure the vacation of a lifetime.
Will I save money on my Winchester car rental if I bundle it with my hotel or flight?
Combining your car, flight and hotel into a Winchester vacation package is the best way to score an amazing deal. Plus, having your own rental car gives you absolute freedom to get to all those big-name sights you’re itching to explore. Sitting 70 mi away from Winchester, Indianapolis Motor Speedway is one attraction that should be on your can’t-miss list. Turn up the tunes and make a day trip of it.
What is the best time of year to go to Winchester?
If you prefer to wander wisely, is a terrific time to do it. That’s when hotel rates are at their lowest. In contrast, prices are at their highest in . December, January and February are the most popular times for a vacation in Winchester, so expect snaking queues for famous attractions. Hoping to avoid high season? You’ll find thinner crowds during June, July and November.
Which airport is best for Winchester?
One option is James M. Cox Dayton Intl. Airport (DAY). From here, you’ll need to travel northwest for about 45 mi to reach inner Winchester. Another great choice is Fort Wayne Intl. Airport (FWA), which is 55 mi away from central Winchester.
What is there to do in Winchester?
While getting off the beaten track is rewarding, you shouldn’t miss the big sights that make a place famous. Winchester Speedway and Winchester Golf Club are just two of them in Winchester.
Where should I stay when visiting Winchester?
Many people check in to the Randolph Inn and Suites. It’s sure to be a good base for your Winchester escape.