Deals on vacations and trips to Winchester

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Holiday Inn Indianapolis Airport by IHG

Holiday Inn Indianapolis Airport by IHG

3 out of 5
Price was $489, price is now $427 per person
$427
per person
Nov 26 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Indianapolis (IND)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like free self parking.
Bottleworks Hotel

Bottleworks Hotel

4.5 out of 5
Downtown Indianapolis
Price was $734, price is now $615 per person
$615
per person
Dec 27 - Dec 30
found 5 hours ago
Roundtrip non-stop flight included
Jacksonville (JAX) 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.
Hilton Garden Inn Bloomington

Hilton Garden Inn Bloomington

3 out of 5
Downtown Bloomington
Price was $1,865, price is now $1,587 per person
$1,587
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) 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 and free WiFi in public areas. Self parking, a coffee shop, and a terrace are also offered.
Hotel Indy, Indianapolis, a Tribute Portfolio Hotel

Hotel Indy, Indianapolis, a Tribute Portfolio Hotel

4 out of 5
Downtown Indianapolis
Price was $542, price is now $468 per person
$468
per person
Nov 26 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Omni Severin Hotel

Omni Severin Hotel

4 out of 5
Downtown Indianapolis
Price was $709, price is now $620 per person
$620
per person
Dec 27 - Dec 30
found 5 hours ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Indianapolis (IND)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.

Top Winchester hotels deals

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!

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
Oct 9 - Oct 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
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
Nov 2 - Nov 3
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
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 12 - Oct 13
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
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
$71 nightly
The price is $80 total per night
$80 total
Nov 2 - Nov 3
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. 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.
Breakfast included
Parking included
Comfort Suites

Comfort Suites

2.5 out of 5
421 Commerce Road, Richmond, IN
Free Cancellation
Reserve now, pay when you stay
$95 nightly
The price is $107 total per night
$107 total
Oct 12 - Oct 13
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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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

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

Winchester Speedway

Winchester Golf Club

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

Winchester Golf Club

Randolph County Courthouse

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?
$427 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