Hotels in Winchester

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Where to stay in Winchester?

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very Good, (1,004 reviews)
Enjoy a quiet respite at this Winchester hotel, featuring a seasonal outdoor pool and complimentary full breakfast. With free parking and helpful staff praised by travelers, you'll find comfort minutes from Wiseman Park and Community Park.
The price is CNY613
CNY676 total
includes taxes & fees
May 18 - May 19
Best Western Winchester Hotel

Value Stay

Value Stay
2.0 star property
Winchester
7.6 out of 10, Good, (147 reviews)
Situated close to Community Park and Wiseman Park, this motel offers convenient amenities including free WiFi and complimentary parking. The 24-hour front desk ensures assistance is always available during your Winchester visit.
The price is CNY402
CNY443 total
includes taxes & fees
May 18 - May 19
Value Stay

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (800 reviews)
Retreat to this quiet Winchester hotel with its peaceful atmosphere and clean rooms. Start your day with a free breakfast, then enjoy a refreshing swim in the indoor pool. The fitness center, free WiFi, and parking enhance your stay near The Holler and Lykins Park.
The price is CNY544
CNY599 total
includes taxes & fees
May 24 - May 25
Baymont by Wyndham Winchester

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (465 reviews)
Discover a tranquil haven where safety and quiet comfort await. Located near The Holler and Lykins Park, this Winchester hotel offers a refreshing seasonal outdoor pool and convenient fitness center, plus free breakfast, WiFi and parking.
The price is CNY911
CNY1,004 total
includes taxes & fees
Jun 14 - Jun 15
Hampton Inn Winchester

Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
2.5 star property
Winchester
9.2 out of 10, Wonderful, (563 reviews)
Set near Wiseman Park, this hotel offers an indoor pool for year-round swimming and a 24-hour fitness center. Free parking makes exploring easy, while the helpful staff ensures a comfortable stay with complimentary breakfast to start your day.
The price is CNY879
CNY969 total
includes taxes & fees
Jun 14 - Jun 15
Holiday Inn Express Lexington East - Winchester by IHG

Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (363 reviews)
Discover a tranquil retreat with an indoor pool for morning swims and full fitness center. Just minutes from Community Park and Wiseman Park, this Winchester hotel offers free WiFi and complimentary parking for easy exploration.
The price is CNY515
CNY568 total
includes taxes & fees
Jun 7 - Jun 8
Comfort Inn Winchester

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,887 reviews)
The price is CNY772
CNY851 total
includes taxes & fees
May 18 - May 19
Natural Bridge State Resort Park

Black Bear Lodge Motel

Black Bear Lodge Motel
2.5 star property
Slade
8.0 out of 10, Very Good, (665 reviews)
Tucked against Natural Bridge State Park, this cozy lodge invites outdoor adventures. Clean rooms with satellite TV await after exploring nearby Red River Gorge. Enjoy the picnic area and free parking while helpful staff ensure a memorable mountain getaway.
The price is CNY600
CNY661 total
includes taxes & fees
May 28 - May 29
Black Bear Lodge Motel

Comfort Inn & Suites Mount Sterling

Comfort Inn & Suites Mount Sterling
2.5 star property
Mount Sterling
7.8 out of 10, Good, (746 reviews)
Start your day with a complimentary breakfast at this quiet Mount Sterling retreat. The indoor pool invites morning dips while the hot tub soothes evening tensions. Clean rooms and attentive staff create a peaceful atmosphere near Old Silo Golf Course.
The price is CNY731
CNY806 total
includes taxes & fees
May 31 - Jun 1
Comfort Inn & Suites Mount Sterling

Ramada Limited Mount Sterling

Ramada Limited Mount Sterling
2.0 star property
Mount Sterling
7.0 out of 10, Good, (813 reviews)
Wake up to free breakfast at this peaceful Mount Sterling retreat near the local library. The helpful staff, indoor pool, and 24-hour fitness center create a welcoming atmosphere, while clean rooms with free WiFi ensure a comfortable business trip.
The price is CNY579
CNY638 total
includes taxes & fees
May 20 - May 21
Ramada Limited Mount Sterling

Holiday Inn Express & Suites Mt Sterling North by IHG

Holiday Inn Express & Suites Mt Sterling North by IHG
2.5 star property
Mount Sterling
8.8 out of 10, Excellent, (607 reviews)
Just minutes from Old Silo Golf Course, this welcoming hotel offers an indoor pool and 24-hour fitness center. Enjoy free breakfast, WiFi, and parking while the attentive staff ensures a comfortable stay near Mount Sterling Library.
The price is CNY954
CNY1,051 total
includes taxes & fees
May 31 - Jun 1
Holiday Inn Express & Suites Mt Sterling North by IHG

Clarion Pointe Richmond North near University

Clarion Pointe Richmond North near University
2.5 star property
Richmond
8.2 out of 10, Very Good, (984 reviews)
Wake up to free continental breakfast on weekdays before exploring nearby E.C. Million Park. This hotel offers clean rooms with complimentary WiFi and parking. University-adjacent location earns praise from guests for its peaceful atmosphere and helpful staff.
The price is CNY546
CNY602 total
includes taxes & fees
Jun 4 - Jun 5
Clarion Pointe Richmond North near University

Red Roof Inn Richmond, KY

Red Roof Inn Richmond, KY
2.5 star property
Richmond
7.4 out of 10, Good, (1,003 reviews)
Discover a quiet retreat with an indoor pool in Richmond's entertainment district. Located near E.C. Million Park and Richmond Area Arts Center, this hotel offers free WiFi and parking. Guests consistently praise the helpful staff, clean rooms, and overall value.
The price is CNY365
CNY402 total
includes taxes & fees
May 24 - May 25
Red Roof Inn Richmond, KY

Super 8 by Wyndham Richmond

Super 8 by Wyndham Richmond
2.0 star property
Richmond
7.8 out of 10, Good, (1,003 reviews)
This quiet Richmond motel offers free WiFi and on-the-go breakfast, making mornings easier. You'll be near E.C. Million Park and Richmond Area Arts Center. Guests consistently praise the helpful staff and clean, restful rooms.
The price is CNY376
CNY415 total
includes taxes & fees
May 18 - May 19
Super 8 by Wyndham Richmond

TownePlace Suites by Marriott Richmond

TownePlace Suites by Marriott Richmond
3.0 star property
Richmond
9.2 out of 10, Wonderful, (285 reviews)
Wake up to free breakfast and energize in the 24-hour fitness center at this welcoming hotel. Conveniently located near Richmond Centre Mall and Cinemark, you'll enjoy free parking and WiFi while exploring local attractions.
The price is CNY981
CNY1,082 total
includes taxes & fees
May 24 - May 25
TownePlace Suites by Marriott Richmond

Comfort Suites Richmond

Comfort Suites Richmond
2.5 star property
Richmond
7.6 out of 10, Good, (748 reviews)
Discover a serene retreat with an indoor pool and fitness center just minutes from Richmond Centre Mall. Free breakfast, WiFi, and parking add exceptional value, while the helpful staff ensures your comfort throughout your stay.
The price is CNY693
CNY763 total
includes taxes & fees
May 19 - May 20
Comfort Suites Richmond

Quality Inn Richmond

Quality Inn Richmond
2.5 star property
Richmond
9.0 out of 10, Wonderful, (1,020 reviews)
Splash into the seasonal outdoor pool at this Richmond hotel, where clean rooms and attentive staff await. Near Richmond Centre Mall and Cinemark, with 24-hour fitness center access. Free breakfast, WiFi, and parking enhance your stay.
The price is CNY674
CNY744 total
includes taxes & fees
Jun 3 - Jun 4
Quality Inn Richmond

Home2 Suites By Hilton Richmond, Ky

Home2 Suites By Hilton Richmond, Ky
3.0 star property
Richmond
9.6 out of 10, Exceptional, (226 reviews)
The price is CNY888
CNY979 total
includes taxes & fees
Jun 4 - Jun 5
Home2 Suites By Hilton Richmond, Ky

Hampton Inn Richmond

Hampton Inn Richmond
2.5 star property
Richmond
9.2 out of 10, Wonderful, (1,008 reviews)
Wake up to a complimentary breakfast at this quiet Richmond hotel before exploring nearby attractions. The indoor pool offers year-round swimming, while convenient highway access and free parking make travel stress-free.
The price is CNY667
CNY735 total
includes taxes & fees
Jun 4 - Jun 5
Hampton Inn Richmond

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
3.0 star property
Lexington
8.8 out of 10, Excellent, (1,146 reviews)
Serene retreat with an indoor pool and fitness center just 15 minutes from Rupp Arena and University of Kentucky. Near interstate access and restaurants, this hotel offers free breakfast, WiFi, and parking. Guests praise the helpful staff and quiet atmosphere.
The price is CNY498
CNY578 total
includes taxes & fees
Jun 16 - Jun 17
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
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.

Get last-minute hotel deals in Winchester and save more

Sign in to unlock great savings.
Showing deals for:May 17 - May 18
Showing deals for:May 18 - May 19

You may also like hotels with pools in Winchester

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.

When is the best time to visit Winchester?

Our prices for hotels in Winchester are cheapest in February
Price trends for hotels in Winchester
Pricing is based on two traveler single night rates
View properties in May
Currently viewing crowd sizes and weather for May.
Typical weather for Winchester
May
High 23°C / low 13°C. Sunny most days.
View properties in May
23°
weather_sun
May, no crowd data, average high temperature 23 degrees Celsius, average low temperature 13 degrees Celsius. Sunny most days.
13°
28°
weather_sun
June, no crowd data, average high temperature 28 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
17°
29°
weather_sun
July, no crowd data, average high temperature 29 degrees Celsius, average low temperature 19 degrees Celsius. Sunny most days.
19°
29°
weather_sun
August, no crowd data, average high temperature 29 degrees Celsius, average low temperature 19 degrees Celsius. Sunny most days.
19°
26°
weather_sun
September, no crowd data, average high temperature 26 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
15°
19°
weather_sun
October, no crowd data, average high temperature 19 degrees Celsius, average low temperature 9 degrees Celsius. Sunny most days.
12°
weather_partly_sunny
November, no crowd data, average high temperature 12 degrees Celsius, average low temperature 3 degrees Celsius. Partly sunny.
weather_cloudy
December, no crowd data, average high temperature 8 degrees Celsius, average low temperature 0 degrees Celsius. Cloudy most days.
ac_unit
January, no crowd data, average high temperature 4 degrees Celsius, average low temperature -3 degrees Celsius. Snow likely.
-3°
weather_cloudy
February, no crowd data, average high temperature 7 degrees Celsius, average low temperature -2 degrees Celsius. Cloudy most days.
-2°
13°
weather_cloudy
March, no crowd data, average high temperature 13 degrees Celsius, average low temperature 3 degrees Celsius. Cloudy most days.
18°
weather_sun
April, no crowd data, average high temperature 18 degrees Celsius, average low temperature 8 degrees Celsius. Sunny most days.
Monthly weather averages (˚C)

Top landmarks in Winchester

Learn more about Winchester

Beneath the shadow of the Bluegrass Heritage Museum, Main Street reveals a parade of antique shops where yesterday's treasures await discovery. The Winchester Opera House stands as a cultural cornerstone in this small Kentucky town with big character. Escape to Daniel Boone National Forest, where hiking trails wind through Appalachian wilderness that would make the legendary frontiersman feel right at home. College Park offers a peaceful retreat when urban exploration tires the feet. Local eateries serve up authentic flavors that chain restaurants can't replicate. For golf enthusiasts, Southwind Golf Course presents challenging fairways with scenic vistas. The Clark County Courthouse anchors the historic downtown, its architecture telling stories of bygone eras without saying a word.

MAY 9, 2023 - WINCHESTER, KENTUCKY - aerial view of historic small town of Winchester with Town Clocktower and historic storefronts and buildings

Check out reviews of Winchester hotels guests love

Frequently asked questions

How much does a hotel room cost in Winchester?
You can find top hotels in Winchester from CNY402 with options to suit your budget and needs. If you're after an affordable hotel in Winchester that meets all of your requirements, set your filters and then sort the results by "Price: low to high".
How can I find deals and earn rewards at Winchester hotels?
Discover great deals on Winchester hotel stays with Hotels.com. Take a look at hotel prices mid-week or during the low season as to find those off-peak deals. If it's a spontaneous trip, check out our last-minute deals on Winchester hotels.
Can I book Winchester hotels with free cancellation?
To book a refundable Winchester hotel on Hotels.com, just filter hotels by "Property cancellation options" and select "Fully refundable property". Most hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.
What are some of the best Winchester hotels with free parking?
If you're exploring by car, finding a great Winchester hotel with free parking is a win. Our travelers' favorites include:
What hotels do travelers like in Winchester?
Can I book refundable hotels in Winchester?
If you want the flexibility to change your plans to Winchester, most properties offer refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Winchester if I want a vacation home instead of a traditional hotel?
Browse 5 vacation homes on our site.
What will the weather in Winchester be like during my visit?
July and August are typically the warmest months in Winchester when the average temp is 72°F. January and February are the coldest months when the average temperature is 38°F. April and July are the months with the most rain.
Why should I book my Winchester accommodation with Hotels.com?
There are lots of reasons to book your Winchester trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.