Deals on vacations and trips to Winchester

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Fourwinds Lakeside Inn & Marina

Fourwinds Lakeside Inn & Marina

3 out of 5
Price was $671, price is now $565 per person
$565
per person
Jul 14 - Jul 17
just found
Roundtrip non-stop flight included
Boston (BOS) to Indianapolis (IND)
This smoke-free hotel features a private beach, a marina, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Enjoy the outdoor pool and perks like free self parking.
The village

The village

4 out of 5
Near Westside
Price was $1,132, price is now $884 per person
$884
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Indianapolis (IND)
This apartment features a terrace, laundry facilities, and free self parking. Business travelers can take advantage of the laundry service. A picnic area, barbecue grills, and a virtual front desk are also on offer.
Homewood Suites by Hilton Indianapolis Northwest

Homewood Suites by Hilton Indianapolis Northwest

3 out of 5
College Park
Price was $1,018, price is now $851 per person
$851
per person
Jun 24 - Jun 28
found 13 hours ago
Roundtrip flight included
Boston (BOS) to Indianapolis (IND)
This hotel features an indoor pool and a 24-hour 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.
Courtyard by Marriott Indianapolis Plainfield

Courtyard by Marriott Indianapolis Plainfield

3 out of 5
Price was $1,001, price is now $841 per person
$841
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Indianapolis (IND)
A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Free self parking, a grocery/convenience store, and a computer station are also offered.
Omni Severin Hotel

Omni Severin Hotel

4 out of 5
Downtown Indianapolis
Price was $898, price is now $755 per person
$755
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip 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 valet parking. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.

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
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.
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
May 1 - May 2
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
Comfort Suites Richmond East

Comfort Suites Richmond East

2.5 out of 5
421 Commerce Road Richmond IN
Free Cancellation
$105 nightly
The price is $118 total per night
$118 total
May 10 - May 11
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.
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
May 3 - May 4
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, dry cleaning, and laundry facilities are also on offer.
Super 8 by Wyndham Muncie/Ball St. College Area

Super 8 by Wyndham Muncie/Ball St. College Area

2 out of 5
3601 W Fox Ridge Ln Muncie IN
Free Cancellation
Reserve now, pay when you stay
$61 nightly
The price is $69 total per night
$69 total
May 31 - Jun 1
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 24-hour business center. Staff at the 24-hour front desk can provide around-the-clock assistance.
Comfort Inn & Suites Muncie Near University

Comfort Inn & Suites Muncie Near University

2.5 out of 5
3400 N Marleon Dr Muncie IN
Free Cancellation
$89 nightly
The price is $100 total per night
$100 total
May 7 - May 8
Total with taxes and fees
This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like self-serve breakfast and free self parking.
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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

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

Winchester Golf Club

3.5/5(4 reviews)

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

Winchester Golf Club

Frequently asked questions

How much are vacation packages to Winchester?
$565 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