Deals on vacations and trips to Winchester

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Bottleworks Hotel

Bottleworks Hotel

4.5 out of 5
Downtown Indianapolis
Price was $1,020, price is now $799 per person
$799
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Indianapolis (IND)
A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Enjoy the steam room and perks like free WiFi. A bar/lounge, a 24-hour front desk, and a coffee shop are also provided.
Holiday Inn Indianapolis Downtown by IHG

Holiday Inn Indianapolis Downtown by IHG

3 out of 5
Downtown Indianapolis
Price was $1,276, price is now $961 per person
$961
per person
Mar 8 - Mar 13
found 3 hours ago
Roundtrip flight included
Phoenix (PHX) to Indianapolis (IND)
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.
Grant Street Inn

Grant Street Inn

3.5 out of 5
Old Northeast Downtown
Price was $1,036, price is now $828 per person
$828
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Indianapolis (IND)
A 24-hour gym, free self parking, and free newspapers are featured at this bed & breakfast. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. A library and luggage storage are also provided.
Hotel Indy, Indianapolis, a Tribute Portfolio Hotel

Hotel Indy, Indianapolis, a Tribute Portfolio Hotel

4 out of 5
Downtown Indianapolis
Price was $1,360, price is now $1,094 per person
$1,094
per person
Mar 8 - Mar 13
found 3 hours ago
Roundtrip flight included
Phoenix (PHX) 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.
Homewood Suites by Hilton Indianapolis-Downtown

Homewood Suites by Hilton Indianapolis-Downtown

3 out of 5
Downtown Indianapolis
Price was $1,702, price is now $1,374 per person
$1,374
per person
Mar 8 - Mar 13
found 3 hours ago
Roundtrip flight included
Phoenix (PHX) to Indianapolis (IND)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Relax with a drink at the bar/lounge and enjoy the free full breakfast each morning.

Top Winchester hotels 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
Get rates
A water park and an indoor pool are featured at this smoke-free vacation home. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the hot tub and conveniences like a garden and laundry facilities.
Pool
Hot Tub
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
Jan 16 - Jan 17
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
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
Jan 16 - Jan 17
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
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
$51 nightly
The price is $57 total per night
$57 total
Jan 18 - Jan 19
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
Indoor Gymnasium, Seasonal Pool, 7 Bedroom, Sleeps 25

Indoor Gymnasium, Seasonal Pool, 7 Bedroom, Sleeps 25

Fort recovery OH
Get rates
This vacation home features a gym and a hot tub. Families will appreciate the playground and onsite laundry facilities. A garden and barbecue grills are also provided.
Pool
Hot Tub
Comfort Suites

Comfort Suites

2.5 out of 5
421 Commerce Road Richmond IN
Free Cancellation
Reserve now, pay when you stay
$91 nightly
The price is $102 total per night
$102 total
Jan 25 - Jan 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
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See all available properties in Winchester
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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?
$799 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