Top 10 Hotels in Winchester, KY from ￥8,075 - Competitive Prices

Our top choices for Winchester hotels

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

1. Value Stay

Winchester

Todd

￥11,487 total

includes taxes & fees

Jun 9 - Jun 10

2. Best Western Winchester Hotel

Winchester

Roy

￥16,786 total

includes taxes & fees

Jun 9 - Jun 10

3. Baymont by Wyndham Winchester

Winchester

Tiffany

￥15,276 total

includes taxes & fees

Jun 28 - Jun 29

4. Comfort Inn Winchester

Winchester

alene

￥13,270 total

includes taxes & fees

Jul 2 - Jul 3

5. Hampton Inn Winchester

Winchester

Andrew

￥23,764 total

includes taxes & fees

Jul 6 - Jul 7

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

6. Holiday Inn Express Lexington East - Winchester by IHG

Winchester

Blake

￥22,794 total

includes taxes & fees

Jul 3 - Jul 4

7. Black Bear Lodge Motel

Slade

Charlotte

￥15,550 total

includes taxes & fees

Jun 15 - Jun 16

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

8. Super 8 by Wyndham Richmond

Richmond

Aman

￥9,763 total

includes taxes & fees

Jun 9 - Jun 10

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

9. Natural Bridge State Resort Park

Slade

Coty jay

￥20,028 total

includes taxes & fees

Jun 14 - Jun 15

10. Days Inn Lexington SE/Hamburg

Lexington

Saelim

￥8,075 total

includes taxes & fees

Jun 30 - Jul 1

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

11. Best Western Paris Inn

Paris

Jaime

￥14,418 total

includes taxes & fees

Jun 11 - Jun 12

12. La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

Lexington

Guy

￥18,252 total

includes taxes & fees

Jun 14 - Jun 15

13. Tru By Hilton Lexington Hamburg

Liberty Area

Sharon

￥16,630 total

includes taxes & fees

Jun 15 - Jun 16

Indoor pool, open 5:00 AM to 10:00 PM, sun loungers

14. Holiday Inn Express Lexington Horse Park Area by IHG

Lexington

Terry

￥17,303 total

includes taxes & fees

Jul 3 - Jul 4

Hypo-allergenic bedding, pillowtop beds, desk, laptop workspace

15. Microtel Inn by Wyndham Georgetown

Georgetown

Leeray

￥13,075 total

includes taxes & fees

Jun 10 - Jun 11

16. Country Inn & Suites by Radisson, Georgetown, KY

Georgetown

Cindy

￥13,253 total

includes taxes & fees

Jun 28 - Jun 29

17. Baymont by Wyndham Georgetown/Lexington North

Georgetown

Sherry

￥12,615 total

includes taxes & fees

Jun 14 - Jun 15

Desk, iron/ironing board, free WiFi, bed sheets

18. Super 8 by Wyndham Georgetown

Georgetown

Alyssa

￥12,016 total

includes taxes & fees

Jun 11 - Jun 12

Blackout drapes, iron/ironing board, free WiFi, bed sheets

19. Motel 6 Lexington I-75 Hamburg

Lexington

Francis

￥8,371 total

includes taxes & fees

Jun 16 - Jun 17

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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

Elwood Hotel & Suites

10/10 Excellent

"Absolutely fantastic stay with our family. The food, staff, location and vibe was perfect."

Natural Bridge State Resort Park

6/10 Okay

"The good: friendly staff; excellent location; nice balcony The bad: rooms are dated; rooms are NOT soundproof (I could hear a neighbor their bathroom); room maintenance could be improved. My sink's hot water wasn't functioning nor could I get the body wash out of the dispenser. They didn't clean or resupply at all during my 5-day stay. Staff ignore the smoking rules, thinking nothing of sitting on the stairs while guests try to carry their luggage up."

DoubleTree Suites by Hilton Hotel Lexington

6/10 Okay

"We loved everything about the hotel until the fire alarm went off some time after midnight. The firemen came gave the all clear. Back to bed. A very comfy bed I might add. Then at around 3:00 am again with the fire alarm. Again the firemen came again gave the all clear. Then around 4 am again with the fire alarm. This time we opted to burn if it was real, and it went back off relatively quickly. Everything about this hotel was lovely other than the firemen came gave alarms. No fire we found out the next morning someone had overflowed their bathroom and water had flowed down into the fire alarm of the lower floor."

Fairfield Inn & Suites by Marriott Lexington North

10/10 Excellent

"The hotel is clean and easily-accessible, and seems to be in a safe area of the town just off the freeway. We checked in in the early hours of the morning, and were greeted promptly by the on-duty manager and checked in without any issue. Breakfast was good the next morning - there were plenty of options available, both hot and cold."

More cheap stays in Winchester

Motel 6 Lexington, KY - Airport

750 Newtown Court Lexington KY

￥8,655

￥10,045 total

Jun 9 - Jun 10

includes taxes & fees

6/10 (1,001 reviews)

Frequently asked questions

What's the best place to stay in Winchester?

Baymont by Wyndham Winchester is one of the top choices for your stay based on our traveler data. This hotel offers free breakfast and an indoor pool. Other good choices for your visit to the area are Holiday Inn Express Lexington Horse Park Area by IHG and La Quinta Inn & Suites by Wyndham Lexington South / Hamburg. See all available top hotels, or vacation rentals in Winchester.

What are some of the best vacation rentals in Winchester?

Near Kentucky State Horse Park 💛The Yalla House🚪 🏇🏼Horse & Bourbon Central🥃: This vacation home rental outside of Winchester is located in a rural location and has a patio, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 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 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 Best Western Winchester Hotel. 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's the best hotel in Winchester with an on-site water park or a water park nearby?

Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min. is a favorite water park hotel in WinchesterCheck out all hotels with or near waterparks 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 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 Community Park, The Holler, and Wiseman Park. A couple of additional sights to add to your agenda are Winchester Traveling Trail and Lykins Park. 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

1. Value Stay

2. Best Western Winchester Hotel

3. Baymont by Wyndham Winchester

4. Comfort Inn Winchester

5. Hampton Inn Winchester

6. Holiday Inn Express Lexington East - Winchester by IHG

7. Black Bear Lodge Motel

8. Super 8 by Wyndham Richmond

9. Natural Bridge State Resort Park

10. Days Inn Lexington SE/Hamburg

11. Best Western Paris Inn

12. La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

13. Tru By Hilton Lexington Hamburg

14. Holiday Inn Express Lexington Horse Park Area by IHG

15. Microtel Inn by Wyndham Georgetown

16. Country Inn & Suites by Radisson, Georgetown, KY

17. Baymont by Wyndham Georgetown/Lexington North

18. Super 8 by Wyndham Georgetown

19. Motel 6 Lexington I-75 Hamburg

Stay near popular Winchester attractions

Winchester Traveling Trail

Learn more about Winchester

Top Winchester Hotel Reviews

Elwood Hotel & Suites

More cheap stays in Winchester

Motel 6 Lexington, KY - Airport

Frequently asked questions

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