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 $940, price is now $710 per person
$710
per person
Aug 10 - Aug 17
just found
Roundtrip flight included
New York (NYC) 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.
Spacious Duplex for 14 in Downtown

Spacious Duplex for 14 in Downtown

3 out of 5
Save 100% on your flight
Price was $2,454, price is now $1,846 per person
$1,846
per person
Jul 31 - Aug 2
found 1 day ago
Roundtrip flight included
New York (NYC) to Indianapolis (IND)
This vacation home features a garden, laundry facilities, and free self parking. Barbecue grills are provided for your convenience.
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 $1,081, price is now $824 per person
$824
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Landing Apartments Indy

Landing Apartments Indy

4 out of 5
Price was $979, price is now $751 per person
$751
per person
Aug 10 - Aug 17
just found
Roundtrip flight included
New York (NYC) to Indianapolis (IND)
This aparthotel features a gym and a seasonal outdoor pool. Guests will appreciate free perks like free self parking and WiFi in public areas. A virtual front desk are provided for your convenience.
The Alexander, Autograph Collection

The Alexander, Autograph Collection

4 out of 5
Downtown Indianapolis
Price was $1,370, price is now $1,065 per person
$1,065
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Indianapolis (IND)
This smoke-free hotel features 3 restaurants, a bar/lounge, and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas, conference space, and valet parking. Self parking, a terrace, and a garden are also offered.

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
Jun 9 - Jun 10
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
Comfort Suites Richmond East

Comfort Suites Richmond East

2.5 out of 5
421 Commerce Road Richmond IN
Free Cancellation
$95 nightly
The price is $107 total per night
$107 total
Jul 5 - Jul 6
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
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
$67 nightly
The price is $75 total per night
$75 total
Jun 21 - Jun 22
Total with taxes and fees
This hotel 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, dry cleaning, and laundry facilities are also on offer.
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
$67 nightly
The price is $75 total per night
$75 total
Jun 9 - Jun 10
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A snack bar/deli and laundry facilities are also provided.
Pet friendly
Parking included
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
Free Cancellation
Reserve now, pay when you stay
$62 nightly
The price is $70 total per night
$70 total
Jun 21 - Jun 22
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a gym on site, and a 24-hour front desk and a fireplace in the lobby are also provided.
Breakfast included
Pet friendly
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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

Winchester Golf Club

3.5/5(4 reviews)

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

Winchester Golf Club

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

Frequently asked questions

How much are vacation packages to Winchester?
$710 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