Winchester Hotels

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Winchester hotels

Randolph Inn and Suites

2.5 star property
9.0 out of 10, Wonderful, (230)
"It was very clean and the staff was very accommodating. It was close to the Walmart for anything that you would need and restaurants."
Randolph Inn and Suites

Surestay By Best Western Greenville

2.5 star property
7.8 out of 10, Good, (364)
"Owner/manager was very helpful and a genuinely person. The bathtub/shower was really scarred up. I would not take a shower in that tub!"
The price is P5,255
P5,951 total
includes taxes & fees
Sep 7 - Sep 8
Surestay By Best Western Greenville

Holiday Inn Express Hotel & Suites Greenville by IHG

2.5 star property
8.6 out of 10, Excellent, (290)
"Loved everything about this hotel!"
The price is P7,991
P9,050 total
includes taxes & fees
Aug 23 - Aug 24
Holiday Inn Express Hotel & Suites Greenville by IHG

Quality Inn Greenville North

2.5 star property
8.2 out of 10, Very Good, (320)
"Nice place"
The price is P6,858
P8,039 total
includes taxes & fees
Sep 12 - Sep 13
Quality Inn Greenville North

The Golden Inn

2.5 star property
9.2 out of 10, Wonderful, (415)
"It is decent, clean, quiet and staff is friendly "
The price is P4,509
P5,107 total
includes taxes & fees
Sep 15 - Sep 16
The Golden Inn

Fairfield Inn by Marriott Richmond

2.5 star property
9.0 out of 10, Wonderful, (503)
"Clean nice property with friendly staff and great fee breakfast."
The price is P6,278
P7,110 total
includes taxes & fees
Aug 24 - Aug 25
Fairfield Inn by Marriott Richmond

Motel 6 Richmond, IN

2.0 star property
7.8 out of 10, Good, (949)
"Friendly staff, nice rooms; great place to stay!"
The price is P3,305
P3,701 total
includes taxes & fees
Sep 1 - Sep 2
Motel 6 Richmond, IN

Holiday Inn Express Richmond by IHG

3.0 star property
8.4 out of 10, Very Good, (747)
"nice place to stay. would stay again if thru the area."
The price is P6,278
P7,032 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn Express Richmond by IHG

Best Western Plus Richmond Indiana I-70

2.5 star property
8.4 out of 10, Very Good, (1002)
"Great stay"
The price is P5,625
P6,300 total
includes taxes & fees
Aug 24 - Aug 25
Best Western Plus Richmond Indiana I-70

Home2 Suites by Hilton Richmond

3.0 star property
9.2 out of 10, Wonderful, (380)
"Awesome stay"
The price is P7,229
P8,096 total
includes taxes & fees
Sep 7 - Sep 8
Home2 Suites by Hilton Richmond

Travelodge by Wyndham Richmond IN

2.0 star property
7.2 out of 10, Good, (431)
"Very comfortable, very good for a quick stay when traveling. The breakfast isn’t much but it’s very comfortable otherwise. "
The price is P3,339
P3,740 total
includes taxes & fees
Aug 18 - Aug 19
Travelodge by Wyndham Richmond IN

Cozy Garden Inn By OYO Hwy 40 Richmond

2.5 star property
6.6 out of 10, (50)
"This hotel submitted a no show charge on my CC even thou we checked in at 7pm on the day we were supposed to and paided in full when checked out. And they still submitted a no show charge from expedia and we have had nothing but issues trying to get it refunded. "
The price is P3,670
P4,595 total
includes taxes & fees
Aug 23 - Aug 24
Cozy Garden Inn By OYO Hwy 40 Richmond

Comfort Suites

2.5 star property
9.4 out of 10, Exceptional, (560)
"Very nice hotel and great price!"
The price is P5,337
P6,091 total
includes taxes & fees
Aug 24 - Aug 25
Comfort Suites

Hampton Inn & Suites Richmond, IN

2.5 star property
9.2 out of 10, Wonderful, (910)
"Well kept and a quiet place to stay. "
The price is P6,258
P7,010 total
includes taxes & fees
Sep 14 - Sep 15
Hampton Inn & Suites Richmond, IN

Quality Inn and Conference Center

2.5 star property
6.8 out of 10, (1004)
"It was a great stay "
The price is P3,590
P4,021 total
includes taxes & fees
Aug 31 - Sep 1
Quality Inn and Conference Center

Richmond Inn & Suites

2.0 star property
7.0 out of 10, Good, (347)
"A good value for a one night stay. Nothing fancy, but quiet and comfortable."
The price is P2,055
P3,158 total
includes taxes & fees
Aug 18 - Aug 19
Richmond Inn & Suites

Red Roof Inn Richmond, IN

2.0 star property
7.0 out of 10, Good, (870)
"Nice place "
The price is P3,046
P3,411 total
includes taxes & fees
Aug 21 - Aug 22
Red Roof Inn Richmond, IN

Baymont by Wyndham Richmond I-70

2.5 star property
8.2 out of 10, Very Good, (1005)
"Nice place to stay! Loved the pool and hot tub!"
The price is P4,315
P4,833 total
includes taxes & fees
Aug 24 - Aug 25
Baymont by Wyndham Richmond I-70

Super 8 by Wyndham Centerville-Richmond

2.0 star property
6.0 out of 10, (320)
"People very nice. Clean room"
The price is P3,625
P4,060 total
includes taxes & fees
Aug 24 - Aug 25
Super 8 by Wyndham Centerville-Richmond

Motel 6 Portland, IN

2.0 star property
6.8 out of 10, (69)
"The staff was very nice and the room was clean with a comfortable bed. The only two things bad were the drinking vending machine was empty and they didn't give us enough pillows, because we are two pillow sleepers."
The price is P4,280
P4,794 total
includes taxes & fees
Aug 25 - Aug 26
Motel 6 Portland, IN
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.
Save an average of 15% on thousands of hotels when you're signed in

Learn more about Winchester

Escape to Winchester! Enjoy its adventures, golf, and history.

Top Winchester Hotel Reviews

Frequently asked questions

What's the best place for a stay in Winchester?

Based on our traveler data, Randolph Inn and Suites is one of the top choices for your stay. This hotel offers free breakfast and an indoor pool. Two other choices for your visit to the area are Baymont by Wyndham Richmond I-70 and Baymont by Wyndham Muncie Near Ball State University. See all available top hotels, or vacation rentals in Winchester.

If I need to cancel my hotel reservation in Winchester, will I receive a refund?

Yes! You'll find that most hotel room reservations are fully refundable provided that you cancel before the hotel’s cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If you have a reservation that's non-refundable, you might still have the option to cancel and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.

Where can I learn more about changing or cancelling my trip to Winchester?

For more information about rescheduling or cancelling your trip to Winchester, go to https://www.expedia.com/service/.

What's the best hotel to stay near Winchester Speedway?

Randolph Inn and Suites is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and an indoor pool. It's located 3.2 mi (5.2 km) from Winchester Speedway. Other good options around the area include Courtyard Muncie at Horizon Convention Center and Holiday Inn Express & Suites Portland, an IHG Hotel.

What about the best place to stay near Winchester Golf Club?

One of the top choices for your stay is Randolph Inn and Suites, located 1.3 mi (2.1 km) from Winchester Golf Club, and this hotel offers free breakfast and an indoor pool. Courtyard Muncie at Horizon Convention Center and Holiday Inn Express & Suites Portland, an IHG Hotel are a couple of other good options within the area.

What are some accommodations with pools in Winchester?

Randolph Inn and Suites: Features free breakfast, an indoor pool, and free parking. Quality Inn and Conference Center and Best Western Classic Inn are a couple of other choices that offer an onsite pool.

What's the best hotel for staying near Indianapolis International Airport (IND)?

Crowne Plaza Indianapolis Airport is a popular 3.5-star hotel featuring a restaurant and an indoor pool. It's located a short 1.8 mi (3 km) from Indianapolis Intl. Airport. Other options near the airport are Clarion Hotel Airport and Catalina Airport Motel.

What's it like staying in Winchester?

Visitors can enjoy all that Winchester has to offer including its golf courses. In Winchester, there are 2 hotels and other accommodations to choose from. Find out more about Winchester.

What are the top places to visit in Winchester?

Favorite places to visit include Winchester Golf Club, Winchester Speedway, and Randolph County Courthouse. Additionally, you might want to add Historic Shopping & Dining District of Winchester, Indiana to your itinerary. Check out what more to see and do in Expedia's Winchester guide.

What's the seasonal weather like in Winchester?

The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 33°F. Average annual precipitation for Winchester is 47 inches.