Top 10 Hotels in Winchester, KY from ₩95,113 - Competitive Prices

Our top choices for Winchester hotels

Best Western Winchester Hotel

Winchester

Kathryn

₩158,911 total

includes taxes & fees

May 26 - May 27

Suite, 1 King Bed, Hot Tub | Free WiFi, bed sheets

Value Stay

Winchester

Todd

₩98,698 total

includes taxes & fees

May 26 - May 27

Baymont by Wyndham Winchester

Winchester

Geri

₩136,658 total

includes taxes & fees

Jun 14 - Jun 15

Suite, 1 King Bed, Non Smoking | Select Comfort beds, in-room safe, desk, laptop workspace

Hampton Inn Winchester

Winchester

Sangramsingh

₩234,571 total

includes taxes & fees

Jun 14 - Jun 15

In-room safe, desk, laptop workspace, blackout drapes

Holiday Inn Express Lexington East - Winchester by IHG

Winchester

Blake

₩215,802 total

includes taxes & fees

Jun 14 - Jun 15

Comfort Inn Winchester

Winchester

Michael

₩122,638 total

includes taxes & fees

Jun 14 - Jun 15

Cabin, 2 Bedrooms, Kitchen | Living area | 32-inch flat-screen TV with cable channels, TV

Natural Bridge State Resort Park

Slade

Coty jay

₩182,099 total

includes taxes & fees

Jun 14 - Jun 15

Black Bear Lodge Motel

Slade

Charlotte

₩147,212 total

includes taxes & fees

Jun 8 - Jun 9

Comfort Inn & Suites Mount Sterling

Mount Sterling

Steve

₩181,725 total

includes taxes & fees

Jun 14 - Jun 15

Ramada Limited Mount Sterling

Mount Sterling

Patrick

₩142,193 total

includes taxes & fees

Jun 10 - Jun 11

Holiday Inn Express & Suites Mt Sterling North by IHG

Mount Sterling

Gretchen

₩225,833 total

includes taxes & fees

Jun 14 - Jun 15

Hypo-allergenic bedding, desk, iron/ironing board, free WiFi

Best Western Paris Inn

Paris

Jaime

₩170,612 total

includes taxes & fees

May 26 - May 27

Clarion Pointe Richmond North near University

Richmond

Jayson

₩137,511 total

includes taxes & fees

Jun 22 - Jun 23

Standard Room, 2 Queen Beds | Desk, blackout drapes, iron/ironing board, free WiFi

Super 8 by Wyndham Richmond

Richmond

Mark

₩92,430 total

includes taxes & fees

May 26 - May 27

TownePlace Suites by Marriott Richmond

Richmond

Cynthia

₩240,902 total

includes taxes & fees

May 31 - Jun 1

Suite, 1 King Bed with Sofa bed, Non Smoking, Hot Tub | Desk, laptop workspace, iron/ironing board, free cribs/infant beds

Comfort Suites Richmond

Richmond

Chris

₩172,189 total

includes taxes & fees

Jun 4 - Jun 5

Quality Inn Richmond

Richmond

Christopher

₩182,341 total

includes taxes & fees

May 31 - Jun 1

Home2 Suites By Hilton Richmond, Ky

Richmond

Jennifer

₩241,615 total

includes taxes & fees

May 31 - Jun 1

Hampton Inn Richmond

Richmond

SATBIR

₩183,599 total

includes taxes & fees

Jun 4 - Jun 5

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

Lexington

Guy

₩127,479 total

includes taxes & fees

Jun 15 - Jun 16

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Stay near popular Winchester attractions

Winchester Traveling Trail

This serene mile-long pathway winds through meadows of Kentucky bluegrass, offering a peaceful escape. Benches and shaded areas make it perfect for a leisurely morning stroll with your leashed dog.

See properties

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.

See all hotels in Winchester

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

Top Winchester Hotel Reviews

Spark by Hilton Lexington Hamburg

10/10 Excellent

"Amazing stay with such friendly staff!"

DoubleTree Suites by Hilton Hotel Lexington

10/10 Excellent

"Had a great time here. Cheryl at the front desk was AWESOME! And idk how many cookies you’re allowed but I got two! Haha anyway, that was fun perk I had forgotten about with Doubletree. The hotel location is a bit interesting that said, lots to do around it! Room was really nice and I loved the color palette of the hotel. I booked it because I liked how different it was. Didn’t disappoint- would stay here again!"

Hyatt Regency Lexington

4/10 Poor

"Below average rooms. Perhaps the heavy use by the various groups attending sporting events and conventions makes it difficult to keep the rooms in top working order. To be a Hyatt property the quality of the experience is way off. The common areas were nice enough, but the room itself was long past its prime. Banged up, roughed up, worn down/out. The only thing you get is location; unless you’re attending something at Rupp or the convention center there is no bang for your buck. Staff at registration truly struggled with their computer system which caused delay in getting checked in. Parking is very inconvenient especially if the weather isn’t perfect…crossing a busy roadway to your vehicle and a ticketing system that requires a validation every time you want to leave the property. A very poor overall experience for the price paid. Stay elsewhere if you’re seeking a quality experience. There’s certainly no luxury at this location."

Fairfield Inn & Suites by Marriott Lexington North

4/10 Poor

"Though we booked a king and it still showed that there were 2 king rooms still two available, we were put into another room. The bed was very uncomfortable we would sink in the middle. There were two different hairs on sheets. There were markings in the bathroom. It goes on. We were very disappointed by our experience."

More cheap stays in Winchester

Motel 6 Lexington, KY - Airport

750 Newtown Court Lexington KY

₩81,944

₩95,113 total

May 26 - May 27

includes taxes & fees

6/10 (1,003 reviews)

Frequently asked questions

What's the best place to stay in Winchester?

The Manchester, located 18.5 mi (29.8 km) from the heart of Winchester, is a top choice for your stay based on our traveler data. Other good choices for your visit to the area are Hotel LEX, Trademark Collection by Wyndham and Holiday Inn Express Lexington Horse Park Area by IHG. 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 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 Paradise Cove Aquatic Center 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 Best Western Winchester Hotel 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 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 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 18 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 Winchester Traveling Trail, Lykins Park, and College Park. A couple of additional sights to add to your agenda are Clark County Public Library and GRCHS Baseball Field. 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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Our top choices for Winchester hotels

Best Western Winchester Hotel

Value Stay

Baymont by Wyndham Winchester

Hampton Inn Winchester

Holiday Inn Express Lexington East - Winchester by IHG

Comfort Inn Winchester

Natural Bridge State Resort Park

Black Bear Lodge Motel

Comfort Inn & Suites Mount Sterling

Ramada Limited Mount Sterling

Holiday Inn Express & Suites Mt Sterling North by IHG

Best Western Paris Inn

Clarion Pointe Richmond North near University

Super 8 by Wyndham Richmond

TownePlace Suites by Marriott Richmond

Comfort Suites Richmond

Quality Inn Richmond

Home2 Suites By Hilton Richmond, Ky

Hampton Inn Richmond

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

Stay near popular Winchester attractions

Winchester Traveling Trail

Learn more about Winchester

Top Winchester Hotel Reviews

Spark by Hilton Lexington Hamburg

More cheap stays in Winchester

Motel 6 Lexington, KY - Airport

Frequently asked questions

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