Deals on vacations and trips to Winchester

Save when you book Winchester package deals

Choose two or more items and save on your trip:

Winchester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Comfort Inn & Suites Indianapolis Northwest - College Park

Comfort Inn & Suites Indianapolis Northwest - College Park

2.5 out of 5
College Park
Price was $320, price is now $267 per person
$267
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Indianapolis (IND)
This hotel features a seasonal outdoor pool and a poolside bar. 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.
Hotel Indy, Indianapolis, a Tribute Portfolio Hotel

Hotel Indy, Indianapolis, a Tribute Portfolio Hotel

4 out of 5
Downtown Indianapolis
Price was $531, price is now $439 per person
$439
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Indianapolis (IND)
This hotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. Valet parking is offered and the front desk is staffed around-the-clock.
Cozy 3BR Home in Bates-Hendricks

Cozy 3BR Home in Bates-Hendricks

3 out of 5
Price was $587, price is now $492 per person
$492
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Indianapolis (IND)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.
Historic Pet-Friendly Home in Downtown

Historic Pet-Friendly Home in Downtown

3 out of 5
Price was $586, price is now $492 per person
$492
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Indianapolis (IND)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, laundry facilities, and barbecue grills are also on offer.
Hampton Inn Indianapolis Downtown Across from Circle Centre

Hampton Inn Indianapolis Downtown Across from Circle Centre

2.5 out of 5
Downtown Indianapolis
Price was $594, price is now $506 per person
$506
per person
Nov 25 - Nov 28
found 12 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Indianapolis (IND)
This hotel doesn't skimp on freebies - guests receive free full breakfast and free WiFi. Traveling on business? Take advantage of the express check-out, laundry service, and valet parking. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.

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
$108 nightly
The price is $121 total per night
$121 total
Oct 18 - Oct 19
Total with taxes and fees
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.
Pool
Breakfast included
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
Get rates
This vacation home features an indoor pool and a hot tub. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. A garden and barbecue grills are also provided.
Pool
Hot Tub
Motel 6 Richmond, IN

Motel 6 Richmond, IN

2 out of 5
6030 National Road East Richmond IN
Free Cancellation
Reserve now, pay when you stay
$59 nightly
The price is $66 total per night
$66 total
Oct 28 - Oct 29
Total with taxes and fees
A gym, free self parking, and laundry facilities are featured at this motel. WiFi in public areas is free. A snack bar/deli is provided and the front desk is staffed around-the-clock.
Pet friendly
Parking included
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
$76 nightly
The price is $85 total per night
$85 total
Oct 25 - Oct 26
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Enjoy the hot tub and free perks like full breakfast and free self parking. A business center, dry cleaning, and laundry facilities are also on offer.
Pool
Hot Tub
Comfort Suites Richmond East

Comfort Suites Richmond East

2.5 out of 5
421 Commerce Road Richmond IN
Free Cancellation
$111 nightly
The price is $125 total per night
$125 total
Oct 25 - Oct 26
Total with taxes and fees
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.
Pool
Breakfast included
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
$110 nightly
The price is $123 total per night
$123 total
Oct 25 - Oct 26
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. 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.
Parking included
Free WiFi
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.

Stay near popular Winchester attractions

Winchester Speedway

7.8/10 (26 reviews)
Catch an event at Winchester Speedway during your trip to Winchester.
See properties

Frequently asked questions

How much are vacation packages to Winchester?
$267 is all you'll need for a memorable vacation in Winchester. Bundle your hotel and flights into a vacation package with Travelocity and see how much the savings start to grow. With these kinds of prices, traveling has never been so accessible.
How long should my Winchester vacation be?
If you need some guidance, most visitors spend roughly 3 nights in Winchester. But to discover the true spirit of this place, stay a bit longer. You'll be able to get to more attractions and really experience the local culture.
Where can I get the best vacation package deals for Winchester?
There are exciting Winchester package deals to be scored with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 worldwide properties? Remember this the next time you're ready to tick another place off your bucket list.
Why should I purchase my Winchester vacation bundle via Travelocity?
We've got a destination for every type of globetrotter, exceptional service and 24/7 customer support. And the icing on the cake is we'll match any better price you come across with our Price Match Guarantee.
Can I save on my Winchester car rental if I combine it with my hotel or flight?
With a Winchester vacation package, you can combine your car, hotel and flight bookings and save some serious money. If you're in the mood to discover the best of this exciting area, why not make a beeline for Indianapolis Motor Speedway? This well-known sight is 70 mi from Winchester. With your own rental car, you'll be there in a flash.
Which airport is best for Winchester?
James M. Cox Dayton Intl. Airport (DAY) is where many travelers arrive. You'll find it 45 mi southeast from downtown Winchester. Alternatively, check out the fares to Fort Wayne Intl. Airport (FWA), which is 55 mi away from central Winchester.
What is there to do in Winchester?
Winchester is overflowing with sights to discover, including Winchester Speedway and Winchester Golf Club. These well-known attractions are at the top of most people's travel schedules.
Where should I stay when visiting Winchester?
If you're searching for someplace comfortable to spend your nights, consider the Randolph Inn and Suites. It's the top choice for many visitors.

Photos of local treasures

Browse Winchester vacation photos for more inspiration

A historic building with a clock tower, a statue, and well-maintained gardens.