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Find hotels in Winchester, KY from AED 185

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Compare 1,119 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Holiday Inn Express Lexington East - Winchester by IHG

2.5 star property
9.4 out of 10, Exceptional, (449)
"Good location for travelers. Easy to find, plenty of parking. Hotel seems new. Modern, clean, welcoming staff. "
The price is AED 404
AED 449 total
includes taxes & fees
8 Jun - 9 Jun
Holiday Inn Express Lexington East - Winchester by IHG

Hampton Inn Winchester

2.5 star property
9.2 out of 10, Wonderful, (423)
"Beds were better than expected "
The price is AED 453
AED 499 total
includes taxes & fees
26 May - 27 May
Hampton Inn Winchester

Best Western Winchester Hotel

2.5 star property
8.4 out of 10, Very Good, (911)
"Staff was friendly and grounds were clean "
The price is AED 312
AED 344 total
includes taxes & fees
18 May - 19 May
Best Western Winchester Hotel

Baymont by Wyndham Winchester

2.5 star property
7.0 out of 10, Good, (676)
"It was a clean and comfortable stay."
The price is AED 278
AED 306 total
includes taxes & fees
18 May - 19 May
Baymont by Wyndham Winchester

Value Stays by OYO I-64

2.0 star property
8.2 out of 10, Very Good, (65)
"Very friendly staff, clean hotel. "
The price is AED 229
AED 253 total
includes taxes & fees
25 May - 26 May
Value Stays by OYO I-64

Comfort Inn

2.5 star property
7.0 out of 10, Good, (328)
"They’re great"
The price is AED 199
AED 219 total
includes taxes & fees
7 Jun - 8 Jun
Comfort Inn

Red Roof Winchester - Lexington East

2.0 star property
6.4 out of 10, (550)
"Staff were really friendly, dog stay free, and the rooms were beautiful"
The price is AED 229
AED 252 total
includes taxes & fees
20 May - 21 May
Red Roof Winchester - Lexington East

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1559)
"Clean, friendly staff, quiet atmosphere, beautiful scenery. "
The price is AED 463
AED 510 total
includes taxes & fees
18 May - 19 May
Natural Bridge State Resort Park

Black Bear Lodge Motel

2.5 star property
8.2 out of 10, Very Good, (520)
"Great location for hiking at Natural Bridge and Red River Gorge!"
The price is AED 312
AED 344 total
includes taxes & fees
20 May - 21 May
Black Bear Lodge Motel

Comfort Inn and Suites

2.5 star property
7.6 out of 10, Good, (607)
"Easy access, clean, good breakfast "
The price is AED 346
AED 381 total
includes taxes & fees
15 Jun - 16 Jun
Comfort Inn and Suites

Ramada Limited Mount Sterling

2.0 star property
6.8 out of 10, (671)
"The staff was great the breakfast was good was happy with everything "
The price is AED 234
AED 258 total
includes taxes & fees
6 Jun - 7 Jun
Ramada Limited Mount Sterling

Best Western Paris Inn

2.5 star property
7.8 out of 10, Good, (296)
"Conveniently located in beautiful horse country."
The price is AED 375
AED 413 total
includes taxes & fees
18 May - 19 May
Best Western Paris Inn

Clarion Pointe Richmond North near University

2.5 star property
8.4 out of 10, Very Good, (752)
"Staff are very pleasant. "
The price is AED 274
AED 302 total
includes taxes & fees
15 Jun - 16 Jun
Clarion Pointe Richmond North near University

Motel 6 Richmond, KY – EKU Campus Area

2.0 star property
7.0 out of 10, Good, (70)
"Nice"
The price is AED 224
AED 247 total
includes taxes & fees
18 May - 19 May
Motel 6 Richmond, KY – EKU Campus Area

Red Roof Inn Richmond, KY

2.5 star property
7.6 out of 10, Good, (1004)
"Wonderful stay!!! Staff incredible and friendly... Bed very comfortable enjoyed my stay"
The price is AED 234
AED 258 total
includes taxes & fees
25 May - 26 May
Red Roof Inn Richmond, KY

Countryside Inn

2.0 star property
5.4 out of 10, (220)
"The bed was the best of the room"
The price is AED 198
AED 218 total
includes taxes & fees
31 May - 1 Jun
Countryside Inn

Super 8 by Wyndham Richmond

2.0 star property
7.6 out of 10, Good, (885)
"Decent hotel for the price"
The price is AED 206
AED 227 total
includes taxes & fees
18 May - 19 May
Super 8 by Wyndham Richmond

Best Western Richmond Hotel

2.5 star property
7.2 out of 10, Good, (1000)
"It was quiet, great bed(s)"
The price is AED 256
AED 282 total
includes taxes & fees
29 May - 30 May
Best Western Richmond Hotel

Days Inn by Wyndham Richmond

2.0 star property
5.6 out of 10, (283)
"Basic maintenance has not been kept up. The bathtub faucet dripped constantly. The clock was broken. The TV turned itself on twice; I had to unplug it to get it to stay off. The walls were very noisy. The heating/AC unit did not function properly. "
The price is AED 190
AED 210 total
includes taxes & fees
19 May - 20 May
Days Inn by Wyndham Richmond

Quality Inn Richmond

2.5 star property
8.8 out of 10, Excellent, (1010)
"Was very quite, rooms look like they have been updated, price was great"
The price is AED 303
AED 334 total
includes taxes & fees
8 Jun - 9 Jun
Quality Inn Richmond
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.
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Learn more about Winchester

Trip time! Discover the local cuisine, hiking, and football in Winchester.

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

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 Stays by OYO I-64 as top choices for your visit. See all available top hotels, or vacation rentals in Winchester.

What are some of the best vacation rentals in Winchester?

Authentic, Rustic, Historic Log Cabin: This vacation home rental outside of Winchester is located in a rural location and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. 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 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?

Best Western Winchester Hotel is a top LGBTQ-friendly hotel that features free breakfast and free parking. Holiday Inn Express Lexington East - Winchester by IHG and Hampton Inn Winchester are two other good options for your stay.

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

Best Western Winchester Hotel is a top hotel 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 Value Stays by OYO I-64 and Baymont by Wyndham 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?

Best Western Winchester Hotel is a top hotel with a seasonal outdoor pool, free full breakfast, and free parking. Other choices that feature an onsite pool include Baymont by Wyndham Winchester and Hampton Inn Winchester. 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?
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 20 hotels and other accommodations to choose from. Find out more about Winchester.

What is there to see in Winchester?

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 Bluegrass Heritage Museum and Southwind Golf Course. 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.