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Our top choices for Winchester hotels

Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
2.5 star property
Winchester
9.4 out of 10, Exceptional, (538 reviews)
  • cleanliness
    Experience the warmth of Winchester with a convenient stay near Wiseman Park.
"Clean room and friendly staff. "
United States
Tyson
The price is AED 323
AED 356 total
includes taxes & fees
15 Feb - 16 Feb
Holiday Inn Express Lexington East - Winchester by IHG

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very Good, (1,000 reviews)
  • cleanliness
    Convenient location near interstate with quiet rooms and seasonal pool.
"Clean room, friendly and fast check in service and had a great nights sleep "
United States
Cynthia
The price is AED 265
AED 293 total
includes taxes & fees
27 Jan - 28 Jan
Best Western Winchester Hotel

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (455 reviews)
  • cleanliness
    Recharge at the peaceful Winchester retreat with a seasonal outdoor pool.
"Would stay there again"
United States
Patricia
The price is AED 389
AED 428 total
includes taxes & fees
15 Feb - 16 Feb
Hampton Inn Winchester

Value Stay

Value Stay
2.0 star property
Winchester
7.8 out of 10, Good, (127 reviews)
  • cleanliness
    Comfortable motel in Winchester with free Wi-Fi and parking near local parks.
"Awesome rooms and service"
United States
Brandon
The price is AED 246
AED 271 total
includes taxes & fees
24 Jan - 25 Jan
Value Stay

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (775 reviews)
  • cleanliness
    Tranquil rooms near Lykins Park with an indoor pool for morning swims.
"Great place for a reasonable price! "
United States
Whitney
The price is AED 281
AED 310 total
includes taxes & fees
27 Jan - 28 Jan
Baymont by Wyndham Winchester

Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (354 reviews)
  • cleanliness
    Discover a peaceful stay in Winchester with a refreshing indoor pool experience.
"This was the second time we’ve stopped here this year. It’s the perfect halfway respite between our home town and our destination. Very clean and comfortable. We will tag this as a regular stop on other trips. "
United States
Noelle
The price is AED 265
AED 293 total
includes taxes & fees
13 Feb - 14 Feb
Comfort Inn Winchester

Red Roof Inn Winchester - Lexington East

Red Roof Inn Winchester - Lexington East
2.0 star property
Winchester
6.4 out of 10, (589 reviews)
  • cleanliness
    Affordable comfort with complimentary Wi-Fi near Winchester attractions.
"Great stay"
United States
Walter
The price is AED 229
AED 252 total
includes taxes & fees
26 Jan - 27 Jan
Red Roof Inn Winchester - Lexington East

Holiday Inn Express Lexington Horse Park Area by IHG

Holiday Inn Express Lexington Horse Park Area by IHG
3.0 star property
Lexington
9.4 out of 10, Exceptional, (2,229 reviews)
  • cleanliness
    Relax in this Art Deco haven near Kentucky Horse Park with a serene pool.
"Room was clean, staff was very helpful, easy parking, decent breakfast"
Canada
Christian
The price is AED 309
AED 358 total
includes taxes & fees
15 Feb - 16 Feb
Holiday Inn Express Lexington Horse Park Area by IHG

Country Inn & Suites by Radisson, Georgetown, KY

Country Inn & Suites by Radisson, Georgetown, KY
3.0 star property
Georgetown
9.0 out of 10, Wonderful, (1,008 reviews)
"Great stay! The hotel is clean, quite, and friendly. The breakfast bar was really good, too. Will definitely stay again."
United States
Sarah
The price is AED 287
AED 317 total
includes taxes & fees
8 Feb - 9 Feb
Country Inn & Suites by Radisson, Georgetown, KY

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,795 reviews)
  • cleanliness
    Find tranquility in Slade with direct Natural Bridge State Park access and seasonal pool.
"Friendly staff, convenient the have a restaurant and tavern on site. There is great hiking right out the back door. Appreciated a quiet stay."
United States
Kimberly
Natural Bridge State Resort Park

Quality Inn Richmond

Quality Inn Richmond
2.5 star property
Richmond
9.0 out of 10, Wonderful, (1,013 reviews)
  • cleanliness
    Unwind at this Richmond hotel with a seasonal pool and complimentary breakfast.
"The room was clean and the bed was super comfortable. "
United States
Elizabeth
The price is AED 327
AED 360 total
includes taxes & fees
6 Feb - 7 Feb
Quality 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, (1,205 reviews)
  • cleanliness
    Peaceful hotel near interstate offers indoor pool for year-round relaxation.
"A very nice hotel "
United States
Dale
The price is AED 320
AED 372 total
includes taxes & fees
25 Jan - 26 Jan
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

Comfort Inn & Suites Mount Sterling

Comfort Inn & Suites Mount Sterling
2.5 star property
Mount Sterling
7.8 out of 10, Good, (711 reviews)
  • cleanliness
    Quiet mountain retreat with an indoor pool for peaceful mornings and soothing evenings.
"We stay here anytime we are in town "
United States
Donn
The price is AED 269
AED 297 total
includes taxes & fees
22 Feb - 23 Feb
Comfort Inn & Suites Mount Sterling

Hampton Inn Nicholasville Brannon Crossing

Hampton Inn Nicholasville Brannon Crossing
2.5 star property
Nicholasville
9.4 out of 10, Exceptional, (248 reviews)
  • cleanliness
    Experience Kentucky hospitality near Blue Grass Airport with free breakfast daily.
"Very nice all around! Would stay again. "
United States
Dave
The price is AED 338
AED 372 total
includes taxes & fees
29 Jan - 30 Jan
Hampton Inn Nicholasville Brannon Crossing

Hampton Inn Richmond

Hampton Inn Richmond
2.5 star property
Richmond
9.2 out of 10, Wonderful, (1,003 reviews)
  • cleanliness
    Modern Richmond hotel with convenient amenities and peaceful atmosphere.
"Clean hotel with friendly staff. "
Canada
Susan
The price is AED 358
AED 395 total
includes taxes & fees
3 Feb - 4 Feb
Hampton Inn Richmond

avid hotel Lexington - Hamburg Area by IHG

avid hotel Lexington - Hamburg Area by IHG
2.5 star property
Lexington
9.2 out of 10, Wonderful, (895 reviews)
  • cleanliness
    Enjoy a workout anytime in Lexington with daily breakfast to fuel your day.
"Great stay"
United States
Amy
The price is AED 257
AED 298 total
includes taxes & fees
26 Jan - 27 Jan
avid hotel Lexington - Hamburg Area by IHG

Comfort Inn Lexington South

Comfort Inn Lexington South
2.5 star property
Nicholasville
8.2 out of 10, Very Good, (616 reviews)
  • cleanliness
    Experience comfort at this Nicholasville hotel with fitness center and friendly staff.
"Room was spotless, staff was very curtious. Great breakfast, great place to stay when passing through. "
United States
Tammy
The price is AED 257
AED 283 total
includes taxes & fees
1 Feb - 2 Feb
Comfort Inn Lexington South

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, (582 reviews)
  • cleanliness
    Relaxing retreat in Mount Sterling with indoor pool and fitness facilities.
"Room was super clean and the woman at the front desk was really nice and very helpful"
United States
mark
The price is AED 327
AED 360 total
includes taxes & fees
1 Feb - 2 Feb
Holiday Inn Express & Suites Mt Sterling North by IHG

Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG
3.0 star property
Lexington
9.0 out of 10, Wonderful, (1,002 reviews)
"Amazing staff especially the lady Nicki who went above and beyond for us during check in "
United States
Jessica
The price is AED 323
AED 375 total
includes taxes & fees
30 Jan - 31 Jan
Holiday Inn Lexington - Hamburg by IHG

Home2 Suites By Hilton Richmond, Ky

Home2 Suites By Hilton Richmond, Ky
3.0 star property
Richmond
9.6 out of 10, Exceptional, (157 reviews)
"Nice room"
United States
Robert
The price is AED 389
AED 428 total
includes taxes & fees
8 Feb - 9 Feb
Home2 Suites By Hilton Richmond, Ky
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.
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Stay near popular Winchester attractions

Learn more about Winchester

Stroll through charming downtown streets lined with local shops and eateries. Tee off at Cassell Creek or Southwind Golf Course, then explore local history at the Bluegrass Heritage Museum.

Thanks to my friend of mine who's recommended me to this spot easy hike short walk to get there
Photo by Nawa Aseen
Open Photo by Nawa Aseen

Top Winchester Hotel Reviews

More cheap stays in Winchester

Hotels in Winchester with star-rating

Find out more about Winchester

Top reasons to visit Winchester

  • Outdoor Adventures: Winchester offers scenic hiking trails and urban parks, perfect for nature lovers and adventure seekers.
  • Charming Downtown: Explore the quaint downtown area filled with friendly locals and local antique shops.
  • Family-Friendly Activities: The rolling hills of Clark County provide a great backdrop for family excursions and activities.
  • Relaxing Atmosphere: Enjoy the low crowds and vibrant atmosphere, making it ideal for a peaceful getaway.
  • Diverse Accommodations: Winchester features a variety of lodging options, catering to all traveler needs.

Find great hotels near Winchester

Discover the charm of Winchester, Kentucky, with a variety of lodging options to suit every traveler. Whether you're seeking a comfortable hotel for business travel, a pet-friendly stay, or an LGBTQIA-welcoming environment, Winchester has it all. From popular chains like Wyndham to unique agritourism properties, you'll find accommodations that offer both comfort and convenience. Explore hotel reviews to find the best fit for your vacation needs in this inviting city.

  • WoodSpring Suites Lexington: Nestled 24.1km from Winchester, WoodSpring Suites Lexington is an ideal choice for business travelers and pet enthusiasts alike. This hotel combines the comforts of home with a functional workspace, making it perfect for extended stays. With pet-friendly policies that include a welcoming environment for dogs, guests can enjoy their vacation without leaving their furry friends behind. Additional amenities such as on-site laundry facilities and fully equipped kitchens make this hotel a practical choice for those seeking comfort and convenience during their stay.
  • GuestHouse Lexington: Located 22.5km from Winchester, GuestHouse Lexington is tailored for family vacations and business trips alike. This welcoming hotel prioritizes the needs of children, offering amenities such as cribs and window guards for safety. Families can benefit from its convenient location, allowing easy access to local attractions. The inviting atmosphere is complemented by friendly service, ensuring that guests feel right at home. Whether you’re traveling for work or leisure, this hotel provides a cozy base for your adventures.
  • Hyatt Place Lexington: Situated 20.9km from Winchester, Hyatt Place Lexington is a contemporary 3-star hotel that caters to families, business travelers, and pet owners. This hotel stands out with its commitment to comfort, featuring spacious rooms and complimentary cribs for families. It also welcomes pets, allowing you to bring your four-legged companions along for the journey. Guests can indulge in a variety of amenities, including a 24/7 gym and a delicious breakfast, making it an excellent choice for those seeking both relaxation and convenience.

Where to stay in Winchester

Winchester, Kentucky, offers a delightful blend of outdoor adventures and scenic beauty. Explore the charming downtown area, where friendly locals enhance your experience. Venture into the rolling hills of Clark County, perfect for excursions and family-friendly activities. Enjoy the low crowds and vibrant atmosphere that make Winchester a favorite destination for travelers seeking both relaxation and adventure.

  • Lexington: As a vibrant metropolis, Lexington serves as a hub for travelers seeking outdoor adventures and family experiences. Located within proximity to Winchester, it boasts a wide range of recreational areas, hiking trails, and campgrounds. With visitor numbers peaking during the summer months of July and August, Lexington is renowned for its lush parks and state parks that invite exploration. Don't miss the chance to visit its sports facilities and stadiums, making it an excellent destination for both nature lovers and sports enthusiasts alike.
  • Mount Sterling: Just 22.5km from Winchester, Mount Sterling is a charming city that offers a blend of outdoor adventures and picturesque scenery. Visitors flock here primarily in March, July, and September, as the area is known for its stunning national state parks and beautiful canyon gorges. The local recreational areas and hiking trails provide ample opportunities for exploration and relaxation in nature. Mount Sterling's inviting atmosphere and scenic landscapes make it a perfect stop for those wanting to enjoy Kentucky's natural beauty.
  • Paris: Located 25.7km away from Winchester, Paris is another delightful city that attracts visitors for its outdoor activities and breathtaking scenery. With peak travel times in April, June, and July, adventurers can enjoy a variety of recreational areas and campgrounds. The nearby hiking trails lead to stunning parks and national state parks, as well as magnificent canyon gorges that showcase the region's natural charm. Paris offers a welcoming community and a serene escape for those looking to immerse themselves in the great outdoors.

Things to do in and around Winchester

Winchester, Kentucky, offers a delightful mix of outdoor adventures and charming activities for visitors. Explore the scenic hiking trails and enjoy the recreational areas perfect for picnicking. Don't miss the opportunity to browse through local antique shops, adding a unique touch to your vacation experience. With its beautiful landscapes and inviting atmosphere, Winchester is an ideal destination for nature lovers and those seeking a relaxing getaway.

Shopping

In Winchester, you can explore local shops and boutiques for unique souvenirs. If you're up for a drive, Hamburg Pavilion and Fayette Mall, both offering diverse shopping experiences, are 13 and 30.6km away respectively. Fiber Frenzy, 48.3km away, is perfect for specialty yarns and crafts.

Recreation

Experience the serene Southwind Golf Course, where you can enjoy a round of golf amidst beautiful landscapes. For adventure, head to Lexington Ice Center for thrilling ice skating. If you're looking for more sports excitement, Applebee's Park offers a vibrant atmosphere for various athletic events.

Adventure

Explore the Legacy Trail, a scenic hiking path located 29.0km from Winchester, perfect for outdoor enthusiasts seeking adventure and beautiful landscapes. Alternatively, visit Shillito Park Tennis Center, located 30.6km away, where you can enjoy thrilling tennis matches in a vibrant atmosphere.

Nightlife

Experience the vibrant nightlife in Winchester by visiting the EKU Center for the Arts for captivating performances and romantic vibes. For family-friendly entertainment, catch a movie at the Kentucky Theater or explore the stars at Hummel Planetarium, both offering a fun atmosphere for all ages.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Winchester

For budget-friendly travel to Winchester, Kentucky, plan your visit between December and February when accommodation prices are lower. Monday is the most affordable day to book, while Saturday tends to be pricier. Use Expedia to find great deals by filtering for the best prices and considering package options that combine flights and hotels. To save on transportation, explore the area on foot or use local public transport. Additionally, seek out free activities in Winchester to enhance your experience without breaking the bank.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Winchester are December to February, where the prices are slightly lower. This is in comparison to April to May and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Winchester is Monday. The most expensive day to stay in Winchester is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia's search tool to customize your preferences, such as your budget, desired location, and preferred hotel type. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in Winchester with your flights and activities through an Expedia package deal.

Find the best attractions in and around Winchester

Winchester, Kentucky, is perfect for outdoor enthusiasts and adventure seekers, offering stunning scenery and a variety of attractions. Highlights include urban parks and state parks, making it an ideal destination for families and culture lovers alike. Whether you're looking to explore nature or enjoy local culture, Winchester has something for everyone, ensuring a memorable vacation experience.

  • Fort Boonesborough State Park: Located 12.9km from Winchester, this picturesque park offers a blend of history and outdoor adventure. Explore scenic trails, enjoy picnicking by the Kentucky River, and discover the replica of the historic fort that played a key role in early American frontier life.
  • Kentucky River Museum: Also 12.9km away, this museum immerses visitors in the rich culture and history of the Kentucky River. Learn about the river's significance to local communities through engaging exhibits and artifacts, making it a great stop for history enthusiasts.
  • Bluegrass Heritage Museum: Situated within Winchester, this museum showcases the vibrant culture and heritage of the Bluegrass region. Through fascinating displays and local artifacts, visitors can gain insight into the area's music, art, and history.

Best time to go to Winchester

The best time to visit Winchester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Winchester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Winchester falls in January, visitor numbers are average and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January32.9°F (0.5°C)Light RainMostly CloudyAverageSlightly Low
February36.9°F (2.7°C)Light RainMostly CloudyAverageSlightly Low
March45.3°F (7.4°C)Light RainMostly CloudyAverageAverage
April54.7°F (12.6°C)Light RainMostly SunnySlightly HighSlightly High
May64.4°F (18.0°C)Light RainMostly SunnyAverageSlightly High
June72.1°F (22.3°C)Light RainMostly SunnyAverageAverage
July75.4°F (24.1°C)Light RainMostly SunnySlightly HighAverage
August74.1°F (23.4°C)Light RainMostly SunnyAverageAverage
September68.2°F (20.1°C)Light RainMostly SunnySlightly HighAverage
October57.0°F (13.9°C)Light RainMostly SunnySlightly LowSlightly High
November45.1°F (7.3°C)Light RainMostly SunnySlightly LowAverage
December38.8°F (3.8°C)Light RainMostly CloudySlightly LowSlightly Low

The nearest major airports for your trip to Winchester

For travelers heading to Winchester, Kentucky, the closest major airport is Lexington, KY (LEX-Blue Grass), situated 37.0km away. Recommended accommodations near the airport include the 4-star Marriott Lexington Griffin Gate Golf Resort & Spa, located 11.3km from the airport, and The Campbell House Lexington, Curio Collection by Hilton, just 6.4km away. The DoubleTree Suites by Hilton Hotel Lexington, also a 4-star hotel, is 12.9km from the airport. These hotels offer various transportation services, including limited-hour airport shuttles and on-request shuttles, ensuring convenient access to Lexington, KY (LEX-Blue Grass) for your travel needs.

Frequently asked questions

What's the best place to stay in Winchester?
Holiday Inn Express Lexington East - Winchester by IHG is ranked highly by Expedia customers. This hotel offers free breakfast and an indoor pool. Reviews from our site also recommend Hampton Inn Winchester and Best Western Winchester Hotel as top choices for your visit. See all available top hotels, or vacation rentals in Winchester.
What are some of the best vacation rentals in Winchester?
Morning View Ranch- Red River Gorge- Indoor Pool open March-Nov. Pet friendly.: This vacation home rental outside of Winchester is located on a river and has an indoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. See all vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes, the majority of hotel bookings are fully refundable if cancelled before the hotel's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you booked a non-refundable reservation, it might still be possible to cancel it and get 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 changing or cancelling your trip to Winchester, head over to our customer service page.
What's the best place to stay for families in Winchester?
Hampton Inn Winchester is a hotel with free parking and free breakfast, and it's a top choice on Expedia for families. Attractions in the area like Lexington Ice Center and Explorium are also fun for kids of all ages. Find more child-friendly accommodations in Winchester.
What is the favorite LGBTQ-friendly accommodation in Winchester?
Holiday Inn Express Lexington East - Winchester by IHG is a top LGBTQ-friendly hotel that features free breakfast and free WiFi. Hampton Inn Winchester and Red Roof Winchester - Lexington East are two other good options for your stay.
What's the best pet-friendly place to stay in Winchester?
Best Western Winchester Hotel is a top hotel for people traveling with their pets, and offers a seasonal outdoor pool and a computer station for its human guests. Other good choices for you and your pet's trip include Hampton Inn Winchester and Baymont by Wyndham Winchester. See more pet-friendly hotel accommodations in Winchester.
Where is the best hotel to stay close to Community Park?
Best Western Winchester Hotel is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and free parking. It's located just a short 0.8 mi (1.3 km) from Community Park. Other good choices within a few miles include Baymont by Wyndham Winchester and Holiday Inn Express Lexington East - Winchester, an IHG Hotel.
What about the best place to stay close to Southwind Golf Course?
One of the top choices for your stay is Best Western Winchester Hotel, located 2.7 mi (4.3 km) from Southwind Golf Course, and this hotel offers free breakfast and free parking. Holiday Inn Express Lexington East - Winchester, an IHG Hotel and Baymont by Wyndham Winchester are two other good choices within 5 miles.
What are some accommodations with pools in Winchester?
Best Western Winchester Hotel is a top hotel with a seasonal outdoor pool, free full breakfast, and free parking. Baymont by Wyndham Winchester is an additional hotel that offers an onsite pool. View all hotels with pools in Winchester.
What's the best hotel in Winchester with an on-site water park or a water park nearby?
What is the best accommodation for staying close to Blue Grass Airport (LEX)?
Chateau Annette is a popular 3.5-star B&B featuring free breakfast and free parking. It's located a short 1.8 mi (3 km) from Blue Grass Airport. Other good choices close to the airport include Comfort Suites and Americas Best Value Inn Blue Grass Airport.
How is it to stay in Winchester?
Visitors to Winchester are sure to enjoy the restaurants. Tourists can also enjoy the city's coffeehouses, shopping, and football games. In Winchester, there are 20 hotels and other accommodations to choose from. Find out more about Winchester.
What is there to see in Winchester?
Landmarks like Bluegrass Heritage Museum, Winchester Opera House, and Clark County Courthouse might be worth a visit. Natural beauty is on display at College Park, GRCHS Baseball Field, and Community Park. A couple of additional sights to add to your agenda are Southwind Golf Course and Clark County Public Library. 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 72°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Winchester is 56 inches.

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