Deals on vacations and trips to Winchester

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Fairfield Inn & Suites by Marriott Indianapolis Downtown

Fairfield Inn & Suites by Marriott Indianapolis Downtown

3 out of 5
Downtown Indianapolis
Save 100% on your flight
Price was $560, price is now $407 per person
$407
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Denver (DEN) to Indianapolis (IND)
This smoke-free hotel features 3 restaurants, a bar/lounge, and a 24-hour gym. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. Valet parking, a 24-hour business center, and a snack bar/deli are also offered.
Marriott Indianapolis Downtown

Marriott Indianapolis Downtown

4 out of 5
Downtown Indianapolis
Save 100% on your flight
Price was $594, price is now $429 per person
$429
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Denver (DEN) to Indianapolis (IND)
This hotel features 2 bars/lounges and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A restaurant, a 24-hour front desk, and a coffee shop are also provided.
Courtyard by Marriott Indianapolis Downtown

Courtyard by Marriott Indianapolis Downtown

3 out of 5
Downtown Indianapolis
Save 100% on your flight
Price was $560, price is now $407 per person
$407
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Denver (DEN) 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, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and a snack bar/deli are also offered.
Conrad Indianapolis

Conrad Indianapolis

5 out of 5
Downtown Indianapolis
Price was $1,346, price is now $998 per person
$998
per person
Mar 9 - Mar 12
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Indianapolis (IND)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Make the most of the indoor pool and hot tub, and relax with drinks at one of the 2 bars/lounges.
SpringHill Suites by Marriott Indianapolis Downtown

SpringHill Suites by Marriott Indianapolis Downtown

3 out of 5
Downtown Indianapolis
Price was $561, price is now $417 per person
$417
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Denver (DEN) to Indianapolis (IND)
This smoke-free hotel features 4 restaurants, a bar/lounge, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Enjoy the free buffet 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
Dec 21 - Dec 22
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
Dec 21 - Dec 22
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

Comfort Suites

2.5 out of 5
421 Commerce Road Richmond IN
Free Cancellation
Reserve now, pay when you stay
$90 nightly
The price is $101 total per night
$101 total
Dec 28 - Dec 29
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
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
$57 nightly
The price is $64 total per night
$64 total
Dec 21 - Dec 22
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
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
Dec 28 - Dec 29
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
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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?
$407 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

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