Photo by Nawa Aseen

Find hotels in Winchester, KY from NT$1,556

    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

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

Compare 1,147 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Value Stay

2.0 star property
8.0 out of 10, Very Good, (84)
"Nice clean place"
The price is NT$1,753
NT$1,933 total
includes taxes & fees
Aug 12 - Aug 13
Value Stay

Super 8 by Wyndham Richmond

2.0 star property
7.6 out of 10, Good, (920)
"It’s clean, and affordable and when you’re looking for a room that’s all that matters!"
The price is NT$1,664
NT$1,834 total
includes taxes & fees
Aug 7 - Aug 8
Super 8 by Wyndham Richmond

Home2 Suites Lexington Keeneland Airport, KY

3.0 star property
9.6 out of 10, Exceptional, (196)
"Incredibly clean, spacious room, terrific lobby, and nice amenities. "
The price is NT$2,958
NT$3,434 total
includes taxes & fees
Aug 29 - Aug 30
Home2 Suites Lexington Keeneland Airport, KY

Black Bear Lodge Motel

2.5 star property
8.2 out of 10, Very Good, (572)
"Great stay!"
The price is NT$2,526
NT$2,784 total
includes taxes & fees
Aug 4 - Aug 5
Black Bear Lodge Motel

Baymont by Wyndham Winchester

2.5 star property
7.2 out of 10, Good, (732)
"Easy to get to. Clean staff were good"
The price is NT$2,384
NT$2,629 total
includes taxes & fees
Aug 10 - Aug 11
Baymont by Wyndham Winchester

Holiday Inn Express Lexington East - Winchester by IHG

2.5 star property
9.4 out of 10, Exceptional, (469)
"Jennifer, at the front desk, was wonderful!"
The price is NT$3,078
NT$3,393 total
includes taxes & fees
Aug 31 - Sep 1
Holiday Inn Express Lexington East - Winchester by IHG

Best Western Winchester Hotel

2.5 star property
8.4 out of 10, Very Good, (956)
"The staff was great. "
The price is NT$2,988
NT$3,294 total
includes taxes & fees
Aug 2 - Aug 3
Best Western Winchester Hotel

Comfort Inn

2.5 star property
7.0 out of 10, Good, (339)
"Hotel was overbooked. We had booked 2 rooms for my wife and 4 kids. Because there were no adjoining rooms we ended up booking just one room. It worked out ok but kind of disappointed."
The price is NT$2,140
NT$2,359 total
includes taxes & fees
Aug 24 - Aug 25
Comfort Inn

Red Roof Winchester - Lexington East

2.0 star property
6.4 out of 10, (566)
"Staff were really friendly, dog stay free, and the rooms were beautiful"
The price is NT$1,861
NT$2,052 total
includes taxes & fees
Aug 5 - Aug 6
Red Roof Winchester - Lexington East

Hampton Inn Winchester

2.5 star property
9.2 out of 10, Wonderful, (434)
"Property was nice"
The price is NT$3,416
NT$3,766 total
includes taxes & fees
Aug 31 - Sep 1
Hampton Inn Winchester

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1644)
"Plenty to do and peaceful"
Natural Bridge State Resort Park

Ramada Limited Mount Sterling

2.0 star property
7.0 out of 10, Good, (720)
"Jaccuzzi in room, nice staff, and nice rooms."
The price is NT$2,413
NT$2,660 total
includes taxes & fees
Aug 2 - Aug 3
Ramada Limited Mount Sterling

Home2 Suites By Hilton Richmond, Ky

3.0 star property
9.6 out of 10, Exceptional, (74)
"Very nice clean hotel staff was amazing pool was saltwater and warm and clean breakfast was good "
The price is NT$3,276
NT$3,612 total
includes taxes & fees
Aug 10 - Aug 11
Home2 Suites By Hilton Richmond, Ky

Days Inn Lexington SE/Hamburg

2.0 star property
7.0 out of 10, Good, (986)
"The staff was very friendly and the rooms were clean"
The price is NT$1,556
NT$1,806 total
includes taxes & fees
Aug 17 - Aug 18
Days Inn Lexington SE/Hamburg

Hampton Inn I-75 Lexington/Hamburg Area

2.5 star property
8.6 out of 10, Excellent, (832)
"Definitely going go stay here next time"
The price is NT$2,556
NT$2,967 total
includes taxes & fees
Aug 9 - Aug 10
Hampton Inn I-75 Lexington/Hamburg Area

Comfort Inn and Suites

2.5 star property
7.6 out of 10, Good, (647)
"It was okay, but we chose it mainly because they are pet friendly."
The price is NT$2,787
NT$3,073 total
includes taxes & fees
Aug 24 - Aug 25
Comfort Inn and Suites

Red Roof Inn Richmond, KY

2.5 star property
7.6 out of 10, Good, (1000)
"Had a good stay"
The price is NT$2,015
NT$2,221 total
includes taxes & fees
Aug 10 - Aug 11
Red Roof Inn Richmond, KY

Comfort Suites Richmond

2.5 star property
7.6 out of 10, Good, (691)
"Staff was very nice and accommodating"
The price is NT$2,537
NT$2,797 total
includes taxes & fees
Sep 1 - Sep 2
Comfort Suites Richmond

Comfort Inn Lexington I-75

2.5 star property
7.4 out of 10, Good, (677)
"Clean and comfortable, nice breakfast buffet "
The price is NT$1,879
NT$2,181 total
includes taxes & fees
Aug 17 - Aug 18
Comfort Inn Lexington I-75

Hyatt Place Lexington

3.0 star property
8.8 out of 10, Excellent, (1004)
"Great place to stay"
The price is NT$2,839
NT$3,295 total
includes taxes & fees
Aug 8 - Aug 9
Hyatt Place Lexington
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

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.

Canoeing down the Kentucky river 🚣
Photo by Hyelsinta
Open Photo by Hyelsinta

Top Winchester Hotel Reviews

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 Value Stay as top choices for your visit. 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, 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 on a budget in Winchester?

Based on reviews, Red Roof Inn Lexington - Winchester is a popular hotel for our travelers who want a more economical choice, and features free WiFi and free parking. View all budget hotels in Winchester.

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 Hummel Planetarium 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. See all available hotels listed as LGBTQ-friendly in Winchester.

What's the best pet-friendly place to stay in Winchester?

Baymont by Wyndham Winchester is a top dog-friendly hotel, and offers an indoor pool and a fitness center for its human guests. Other good choices for you and your pet's trip include Value Stay and Hampton Inn 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's the best golf hotel in Winchester?

House on Belmont is a B&B featuring free breakfast and laundry facilities, and it's a top choice for golfing nearby. Visit Southwind Golf Course or Cassell Creek Golf Course to perfect your golf swing. See more golf hotels in Winchester.

What are some accommodations with pools in Winchester?

Baymont by Wyndham Winchester is a top hotel with a pool, free breakfast, and free WiFi. Best Western Winchester Hotel is an additional hotel that offers an onsite pool. View all hotels with pools in Winchester.

What is the best spa hotel in Winchester?

Baymont by Wyndham Winchester is a top spa hotel featuring a pool and a fitness center. See all spa hotels in Winchester.

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. A top sight in the area is Kentucky Horse Park. In Winchester, there are 21 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 Lykins Park, College Park, and GRCHS Baseball Field. 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.