Beginning of main content

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save up to 50% on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Tonight
This weekend
Oct 18 - Oct 20
Next weekend
Oct 25 - Oct 27

Top Rated Winchester Hotels

Red Roof Inn Lexington - Winchester
Red Roof Inn Lexington - Winchester
2.0 out of 5.0 1100 Interstate Drive, Winchester, KY
Free Cancellation
$45
2.8/5 (16 reviews)

The location wasn't the best. The lobby smelled of some kind of industrial cleaner. Ceiling tiles were missing and there was a cluster of buckets and waste baskets catching a leak in the breakfast area.

Reviewed on Jul 16, 2019
Red Roof Inn Lexington - Winchester features free WiFi in public areas, a meeting room, and a business center. You can put free parking to good use if you drive. ...
Best Western Winchester Hotel
Best Western Winchester Hotel
2.5 out of 5.0 1307 W Lexington Ave, Winchester, KY
Free Cancellation
$72
3.6/5 (19 reviews)

It was a convenient, clean , and quiet place to stay.

Reviewed on Jul 31, 2019
Guests of Best Western Winchester Hotel enjoy an outdoor pool, free WiFi in public areas, and a business center. Free parking is included with your stay. Front-desk ...
Hampton Inn Winchester
Hampton Inn Winchester
2.5 out of 5.0 1025 Early Dr, Winchester, KY
$125
4.7/5 (3 reviews)

The staff were super friendly and helpful. The breakfast was great and we arrived during the early evening hours when they had light snacks available for dinner. We were impressed.

Reviewed on Aug 10, 2019
Guests of Hampton Inn Winchester have access to an outdoor pool, a fitness center, and free WiFi in public areas. If you plan to drive, free parking is available. ...
Holiday Inn Express Lexington East - Winchester
Holiday Inn Express Lexington East - Winchester
2.5 out of 5.0 100 Winchester Plaza, Winchester, KY
Free Cancellation
$94
4.7/5 (3 reviews)

Hotel was clean and convenient location. The bed were comfortable and slept well exactly what you ask for in a hotel.

Reviewed on Apr 7, 2019
At Holiday Inn Express Lexington East - Winchester, guests enjoy an indoor pool, a 24-hour fitness center, and free WiFi in public areas. A stay here includes ...
Comfort Inn
Comfort Inn
2.5 out of 5.0 5250 Revilo Rd, Winchester, KY
Free Cancellation
$76
3.5/5 (12 reviews)

Property was right off the interstate and I was traveling west. Have stayed here before. Never disappointed.

Reviewed on Jun 27, 2019
At Comfort Inn, guests have access to a fitness center, free WiFi in public areas, and a 24-hour business center. If you plan to drive, free parking is available. ...
Baymont by Wyndham Winchester
Baymont by Wyndham Winchester
2.5 out of 5.0 960 Interstate Dr, Winchester, KY
Get Rates
2.3/5 (19 reviews)

When we got there they informed us they cannot receive online reservations. And they wouldn’t give us a room. My debit card was charged $89.13 and we still had to find another hotel

Reviewed on Apr 29, 2019
At Baymont by Wyndham Winchester, guests enjoy features like an indoor pool, a fitness center, and a spa tub. Free parking is available if you drive. Front-desk ...
Hyatt Regency Lexington
Hyatt Regency Lexington
3.5 out of 5.0 401 W High St, Lexington, KY
Free Cancellation
$140
4.2/5 (63 reviews)

Great location! Right next to UK campus and steps to downtown action. Breakfast buffet was decent, the bar is good, fitness center needs to step it up but it served the purpose;)

Reviewed on Oct 7, 2019
Guests of Hyatt Regency Lexington have access to an indoor pool, a 24-hour fitness center, and free WiFi in public areas. Onsite parking is available, both free ...
GuestHouse Lexington
GuestHouse Lexington
2.5 out of 5.0 2261 Elkhorn Road, Lexington, KY
Free Cancellation
$55
4.2/5 (58 reviews)

What a great hotel. Clean with plenty of room. Loved all the horse details everywhere!

Reviewed on Jul 25, 2019
Guests staying at GuestHouse Lexington enjoy an indoor pool, a fitness center, and free WiFi in public areas. If you drive, take advantage of free parking. The ...
Red Roof Inn Lexington South
Red Roof Inn Lexington South
2.0 out of 5.0 2651 Wilhite Dr, Lexington, KY
Free Cancellation
$48
3.1/5 (52 reviews)

The rooms are redone and are very spacious and redone. But the rooms still smell like cigarette smoke. The hotel is in a very walkable location.

Reviewed on Oct 13, 2019
Red Roof Inn Lexington South features free WiFi in public areas, conference space, and coffee in a common area. Free parking is available if you drive. The 24-hour ...

Luxury Hotels in Winchester

See all 268 Properties in Winchester

Pet Friendly Winchester Hotels

See all 268 Properties in Winchester

Finding a Hotel in Winchester


So you're thinking about a getaway to Winchester? If you want a place to call home that's located close to Winchester attractions, use Orbitz to pick your travel dates, and then presto! Review the list of hotels and other accommodations to find those that are close to what you want to see.


Whether you want to find a B&B or a budget-friendly motel, Winchester has 7 lodging choices including:

  • 4 hotels
  • 2 motels

We make it easy to find a convenient flight into Lexington, KY (LEX-Blue Grass), which is 25.1 mi (40.5 km) from the heart of the city. Find the ideal flight quickly by using the filters on our site to narrow down your search.


Accommodations in Winchester


Orbitz can help you find lodging that has all the amenities you want in a hotel, whether that's free parking, a kitchen, or a swimming pool.

If you want to grab a bite before hitting the road to discover your surroundings, consider one of these Winchester properties, known for their free breakfast:

  • Comfort Inn
  • Baymont by Wyndham Winchester
  • Red Roof Inn Lexington - Winchester

Take a dip when you stay at one of these Winchester properties, noted for their pools.

  • Baymont by Wyndham Winchester
  • Hampton Inn Winchester
  • Comfort Inn

What's the Weather Like in Winchester?


Debating whether you're going to need socks with your sandals while you're here? Winchester is typically warmest in July and August, while it’s usually the chilliest in January and December. The rainiest months are May and July, while the driest months are normally October and September. Here's a summary of rain and seasonal temperatures so you'll be fully prepared for all that Mother Nature can deliver:


  • January to March: average temp during the day is 61°F and 21°F at night
  • April to June: average temp during the day is 85°F and 35°F at night
  • July to September: average temp during the day is 86°F and 47°F at night
  • October to December: average temp during the day is 73°F and 21°F at night
  • Annual rainfall average: 45.59 inches

Things to See and Do in Winchester


While you're here, you may want to grab some grub or libations at the restaurants Winchester is known for. Explore these well-known attractions during your visit:

  • Bluegrass Heritage Museum
  • Southwind Golf Course
  • Lykins Park
  • Community Park
  • Cassell Creek Golf Course
  • Rupp Arena

Recent Reviews

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.