Deals on vacations and trips to Winchester

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Winchester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Wyndham Indianapolis Airport

Wyndham Indianapolis Airport

3.5 out of 5
Price was $539, price is now $484 per person
$484
per person
Dec 29 - Jan 1
found 23 hours ago
Roundtrip flight included
Washington (WAS) 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 free airport shuttle. Enjoy the seasonal outdoor pool and perks like free self parking.
Landing Furnished Apartments Near Northside

Landing Furnished Apartments Near Northside

4 out of 5
Near Northside
Price was $730, price is now $632 per person
$632
per person
Dec 29 - Jan 1
found 23 hours ago
Roundtrip flight included
Washington (WAS) to Indianapolis (IND)
This apartment features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, a lobby fireplace, and a picnic area are also offered.
Terre Haute Casino Resort - Adults Only

Terre Haute Casino Resort - Adults Only

4 out of 5
Price was $730, price is now $641 per person
$641
per person
Dec 16 - Dec 20
found 1 day ago
Roundtrip flight included
Washington (WAS) to Indianapolis (IND)
A casino, 5 restaurants, and a 24-hour gym are all featured at this resort. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Relax with a drink at one of the 6 bars/lounges and enjoy perks like free self parking.
Holiday Inn Express & Suites Terre Haute by IHG

Holiday Inn Express & Suites Terre Haute by IHG

2.5 out of 5
Price was $571, price is now $506 per person
$506
per person
Dec 16 - Dec 20
found 1 day ago
Roundtrip flight included
Washington (WAS) to Indianapolis (IND)
This hotel features a 24-hour gym and a hot tub. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
JW Marriott Indianapolis

JW Marriott Indianapolis

4 out of 5
Downtown Indianapolis
Price was $630, price is now $565 per person
$565
per person
Dec 29 - Jan 1
found 23 hours ago
Roundtrip flight included
Washington (WAS) 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.

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
Nov 2 - Nov 3
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
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
$58 nightly
The price is $65 total per night
$65 total
Nov 8 - Nov 9
Total with taxes and fees
A gym, free self parking, and laundry facilities are featured at this motel. WiFi in public areas is free. A snack bar/deli is provided and the front desk is staffed around-the-clock.
Pet friendly
Parking 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
$76 nightly
The price is $85 total per night
$85 total
Nov 8 - Nov 9
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Enjoy the hot tub and free perks like full breakfast and free self parking. A business center, dry cleaning, and laundry facilities 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
$104 nightly
The price is $116 total per night
$116 total
Nov 8 - Nov 9
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
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
$93 nightly
The price is $105 total per night
$105 total
Nov 7 - Nov 8
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.

Stay near popular Winchester attractions

Winchester Speedway

7.8/10 (26 reviews)
Catch an event at Winchester Speedway during your trip to Winchester.
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Frequently asked questions

How much are vacation packages to Winchester?
$484 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

A historic building with a clock tower, a statue, and well-maintained gardens.