Deals on vacations and trips to Winchester

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Holiday Inn Express Hotel & Suites Greenwood by IHG

Holiday Inn Express Hotel & Suites Greenwood by IHG

2.5 out of 5
Price was $541, price is now $432 per person
$432
per person
Jun 23 - Jun 26
found 1 day ago
Roundtrip flight included
Austin (AUS) to Indianapolis (IND)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Ironworks Hotel Indy

Ironworks Hotel Indy

4 out of 5
Price was $1,033, price is now $789 per person
$789
per person
Jun 23 - Jun 26
found 1 day ago
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.
Royal Inn Rockville IN by Hotel O

Royal Inn Rockville IN by Hotel O

3 out of 5
Price was $562, price is now $435 per person
$435
per person
May 14 - May 18
found 4 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Indianapolis (IND)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.
Spacious 5-Bedroom Blue Bungalow

Spacious 5-Bedroom Blue Bungalow

3 out of 5
Price was $1,032, price is now $804 per person
$804
per person
May 16 - May 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Indianapolis (IND)
This vacation home features laundry facilities. Take advantage of the free self parking.
The village

The village

4 out of 5
Near Westside
Price was $678, price is now $542 per person
$542
per person
May 16 - May 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Indianapolis (IND)
This apartment features a terrace, laundry facilities, and free self parking. Business travelers can take advantage of the laundry service. A picnic area, barbecue grills, and a virtual front desk are also on offer.

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
Apr 15 - Apr 16
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
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
$70 nightly
The price is $79 total per night
$79 total
Apr 26 - Apr 27
Total with taxes and fees
This inn features an indoor pool and a 24-hour gym. Enjoy the hot tub and free perks like self-serve breakfast and free self parking. A business center, free WiFi in public areas, and dry cleaning 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
$114 nightly
The price is $127 total per night
$127 total
Apr 27 - Apr 28
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
Comfort Inn & Suites Muncie Near University

Comfort Inn & Suites Muncie Near University

2.5 out of 5
3400 N Marleon Dr Muncie IN
Free Cancellation
$89 nightly
The price is $100 total per night
$100 total
Apr 21 - Apr 22
Total with taxes and fees
This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like self-serve breakfast and free self parking.
Pool
Breakfast included
Best Western Plus Richmond Indiana I-70

Best Western Plus Richmond Indiana I-70

2.5 out of 5
533 W Eaton Pike Richmond IN
Free Cancellation
Reserve now, pay when you stay
$101 nightly
The price is $113 total per night
$113 total
Apr 20 - Apr 21
Total with taxes and fees
This hotel features an indoor pool and a gym. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A business center, dry cleaning, and luggage storage are also on offer.
Pool
Breakfast included
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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

Winchester Speedway

4/5(16 reviews)

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

Winchester Speedway

Randolph County Courthouse

4/5(1 review)

After visiting Randolph County Courthouse, make a plan to see the other sights and activities in Winchester.

Randolph County Courthouse

Winchester Golf Club

3.5/5(4 reviews)

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

Winchester Golf Club

Frequently asked questions

How much are vacation packages to Winchester?
$432 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