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Find Hotels in Winchester, KY

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Winchester hotels and places to stay

Lexington Griffin Gate Marriott Golf Resort & Spa
4 out of 5
1800 Newtown Pike, Lexington, KY
Free CancellationReserve now, pay when you stay
The price is $99 per night
20.43 mi from city center
4/5Very Good! (363 reviews)

"Good check in. Very basic Property but clean and has comfortable beds"…"

Reviewed on Jun 2, 2020

Lexington Griffin Gate Marriott Golf Resort & Spa
SpringHill Suites Lexington Near the University of Kentucky
3 out of 5
863 South Broadway, Lexington, KY
Free CancellationReserve now, pay when you stay
The price is $70 per night
20.66 mi from city center
4.4/5Excellent! (866 reviews)

"The propery was clean and had a pleasant odor. The breakfast was basic but good. The only 1 thing i didnt like was the tub had a rust stain. Overall I had a wonderful experience at this hotel and would stay again."…"

Reviewed on Mar 9, 2020

SpringHill Suites Lexington Near the University of Kentucky
Motel 6 Lexington, KY- Airport
2 out of 5
750 Newtown Court, Lexington, KY
Free Cancellation
The price is $49 per night
20.38 mi from city center
2.9/5 (651 reviews)

"Have been staying here for a few months and the staff are always friendly and very helpful. The rooms are very clean and housekeeping comes in each day and sanitizes our room due to the virus pandemic. The rates are great I can only complain about one thing here and that is the guest that throw trash ..."…"

Reviewed on May 30, 2020

Motel 6 Lexington, KY- Airport
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Hyatt Place Lexington
3 out of 5
2001 Bryant Rd, Lexington, KY
Free CancellationReserve now, pay when you stay
The price is $93 per night
14.9 mi from city center
4.4/5Excellent! (1,111 reviews)

"Nice place. Nice location with easy access to I-75. Quiet place with clean rooms and friendly staff."…"

Reviewed on Jun 1, 2020

Hyatt Place Lexington
Best Western Winchester Hotel
2.5 out of 5
1307 W Lexington Ave, Winchester, KY
Free CancellationReserve now, pay when you stay
The price is $68 per night
3.85 mi from city center
4.1/5Very Good! (450 reviews)

"Clean room and good breakfast. Pleasant staff. Easy access to dining and shopping"…"

Reviewed on Mar 14, 2020

Best Western Winchester Hotel
GLō Best Western Lexington
3 out of 5
1935 Stanton Way, Lexington, KY
Free CancellationReserve now, pay when you stay
The price is $85 per night
20.58 mi from city center
4.6/5Exceptional! (673 reviews)

"Clean hotel very easy to check in and move to room."…"

Reviewed on Jun 2, 2020

GLō Best Western Lexington
Baymont by Wyndham Winchester
2.5 out of 5
960 Interstate Dr, Winchester, KY
Free CancellationReserve now, pay when you stay
The price is $48 per night
3.25 mi from city center
3.1/5 (293 reviews)
stay

"very nice staff overall good stay"…"

Reviewed on Feb 23, 2020

Baymont by Wyndham Winchester
Red Roof Inn Lexington
2 out of 5
1980 Haggard Ct, Lexington, KY
Free CancellationReserve now, pay when you stay
The price is $54 per night
18.69 mi from city center
3.6/5Good! (980 reviews)

"Everyone was great and the service is great and the property is great really nice thank you."…"

Reviewed on May 15, 2020

Red Roof Inn Lexington
Holiday Inn Express Lexington East - Winchester
2.5 out of 5
100 Winchester Plaza, Winchester, KY
Free Cancellation
The price is $108 per night
4.56 mi from city center
4.6/5Exceptional! (62 reviews)

"I loved the room darkening shades. The beds were comfortable. Breakfast was wonderful! I loved the hot options (bacon, omelets, pancakes, sausage, biscuits, gravy...). Staff were very friendly and helpful. The hotel is new so it was very clean. The pool was very nice but still a bit on the chilly ..."…"

Reviewed on Mar 9, 2020

Holiday Inn Express Lexington East - Winchester
Red Roof Inn Lexington - Winchester
2 out of 5
1100 Interstate Drive, Winchester, KY
Free CancellationReserve now, pay when you stay
The price is $51 per night
3.26 mi from city center
3.1/5 (385 reviews)

"We booked this room because of the price and the offering of breakfast. We were traveling to Louisville for the farm show and only planned to stay one night. We were so pleased with the room, staff, and wonderful breakfast that we decided to stay again the following night on our way home. We highly ..."…"

Reviewed on Feb 15, 2020

Red Roof Inn Lexington - Winchester
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Visiting Winchester

Visitors to Winchester are sure to enjoy the restaurants. Tourists can also enjoy the city's coffeehouses, shopping, and football games. Top sights in the area include Rupp Arena, Mary Todd Lincoln House, and Kroger Field.

  • You'll find 217 Expedia hotels and other accommodations in the larger area of Lexington
  • The closest major airport is in Lexington, KY (LEX-Blue Grass), 25.1 mi (40.5 km) from the city center

Sightseeing and Staying in Winchester

The picturesque setting of Lykins Park and Community Park exemplify the city's natural beauty. A couple of additional sights to add to your agenda are Bluegrass Heritage Museum and Southwind Golf Course.

As you plan your vacation, you'll find 6 hotels and other lodging options available to pick from in Winchester. These are highly ranked ones based on our user reviews:

  • Hampton Inn Winchester - This 2.5-star hotel features free breakfast, free WiFi, and free parking. It's a favorite with Expedia travelers for its breakfast and clean, comfortable rooms.
  • Best Western Winchester Hotel - Our customers like the overall value and clean, comfortable rooms at this motel. This 2.5-star motel features free breakfast, an outdoor pool, and free WiFi.
  • Comfort Inn - This 2.5-star hotel features free breakfast, an indoor pool, and free WiFi. Expedia customers like its breakfast and helpful staff.

Outside the city, top places to visit include Kroger Field, located 20 mi (32.3 km) from the heart of the city, and Mary Todd Lincoln House, which is 20.3 mi/32.6 km away.

Dressing for Winchester

  • Between January and March, you can expect the daytime average to be around 61°F and the nighttime average to be 21°F
  • From April to June, temperatures average about 85°F during the day and 35°F at night
  • July through September averages 86°F during the day and 47°F at night
  • In October-December, the average temperature is 73°F during the day and 21°F at night
  • About 45.59 inches of rain falls on Winchester each year
  • Hottest months are usually July and August with an average temperature of 85°F, while the coldest months are January and December with an average of 22°F

Frequently asked questions

What's the best place to stay in Winchester?
Holiday Inn Express Lexington East - Winchester is ranked highly by Expedia customers. This hotel offers free breakfast and an indoor pool. Reviews from our site also recommend Best Western Winchester Hotel and Comfort Inn as top choices for your visit.
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. Enter dates in and click on “Search”, then filter by “free cancellation” to view the best options available 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 on a budget in Winchester?
Based on reviews, Red Roof Inn Lexington - Winchester is a popular 2-star property for our travelers looking for an economical choice, and features free WiFi and air conditioning. Other good options for your budget-friendly stay include Best Western Winchester Hotel and Baymont by Wyndham Winchester.
What's the best place to stay for families in Winchester?
Best Western Winchester Hotel is a property with free parking and free breakfast, and it’s a top choice on Expedia for families. Other choices for your family trip include Comfort Inn and Red Roof Inn Lexington - Winchester. Attractions in the area like Paradise Cove Aquatic Center are also fun for the whole family.
What's the best pet-friendly place to stay in Winchester?
Best Western Winchester Hotel is a top property 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 Baymont by Wyndham Winchester and Red Roof Inn Lexington - 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 property offers free breakfast and an outdoor pool. It’s located just a short 0.8 mi (1.3 km) from Community Park. Other good choices within 5 miles include Red Roof Inn Lexington - Winchester and Hampton Inn Winchester.
What about the best place to stay close to Southwind Golf Course?
One of the top choices for your stay is Red Roof Inn Lexington - Winchester, located 3.6 mi (5.9 km) from Southwind Golf Course, and this property offers free breakfast and free WiFi. Best Western Winchester Hotel and Holiday Inn Express Lexington East - Winchester are a couple of other good options within 5 miles.
What's the best golf hotel in Winchester?
Best Western Winchester Hotel is a property featuring free breakfast and free WiFi, and it’s a top choice for playing a round of golf. Visit Southwind Golf Course or Cassell Creek Golf Course to perfect your golf swing.
What are some accommodations with pools in Winchester?
Comfort Inn is a top hotel with an indoor pool, free buffet breakfast, and free WiFi. A couple of other options that offer an onsite pool include Baymont by Wyndham Winchester and Best Western Winchester Hotel.
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. Top sights in the area include Rupp Arena, Kentucky Horse Park, and The Mall At Lexington Green. In Winchester, there are 8 hotels and other accommodations to choose from.

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