Photo by Hyelsinta

Find hotels in Winchester, KY from AED 181

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Compare 1,095 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Hampton Inn Winchester

2.5 star property
9.2 out of 10, Wonderful, (412)
"Close to town. "
The price is AED 479
AED 528 total
includes taxes & fees
30 Mar - 31 Mar
Hampton Inn Winchester

Holiday Inn Express Lexington East - Winchester by IHG

2.5 star property
9.4 out of 10, Exceptional, (438)
"Our room was spacious. The breakfast spread had lots of options. The room had plenty of outlets for charging devices. "
The price is AED 382
AED 425 total
includes taxes & fees
30 Mar - 31 Mar
Holiday Inn Express Lexington East - Winchester by IHG

Best Western Winchester Hotel

2.5 star property
8.4 out of 10, Very Good, (897)
"This place was very clean, quiet, and close to many businesses. The rooms were VERY well kept for the price of the stay. They are SERIOUS about their Pet Policy though, so be aware before booking the room."
The price is AED 312
AED 344 total
includes taxes & fees
25 Mar - 26 Mar
Best Western Winchester Hotel

Baymont by Wyndham Winchester

2.5 star property
7.0 out of 10, Good, (651)
"Spacing, clean room. Great value for the price."
The price is AED 278
AED 306 total
includes taxes & fees
25 Mar - 26 Mar
Baymont by Wyndham Winchester

Value Stays by OYO I-64

2.0 star property
8.6 out of 10, Excellent, (56)
"They don't have elevators "
The price is AED 269
AED 296 total
includes taxes & fees
30 Mar - 31 Mar
Value Stays by OYO I-64

Red Roof Winchester - Lexington East

2.0 star property
6.4 out of 10, (542)
"Friendly staff. Clean comfortable room"
The price is AED 208
AED 229 total
includes taxes & fees
27 Mar - 28 Mar
Red Roof Winchester - Lexington East

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1509)
"Great property"
The price is AED 444
AED 490 total
includes taxes & fees
6 Apr - 7 Apr
Natural Bridge State Resort Park

Black Bear Lodge Motel

2.5 star property
8.2 out of 10, Very Good, (492)
"The room was very clean. We slept really well. Was cute like a log cabin room. We were able to walk across the road and get food and listen to some really good music. The location is great close to the highway and there is a very quaint coffee shop breakfast place very close. The parking is great."
The price is AED 312
AED 344 total
includes taxes & fees
27 Mar - 28 Mar
Black Bear Lodge Motel

Comfort Inn and Suites

2.5 star property
7.6 out of 10, Good, (587)
"Great price"
The price is AED 305
AED 336 total
includes taxes & fees
20 Apr - 21 Apr
Comfort Inn and Suites

Ramada Limited Mount Sterling

2.0 star property
6.8 out of 10, (645)
"Can’t wait to come back really enjoyed it."
The price is AED 293
AED 323 total
includes taxes & fees
27 Mar - 28 Mar
Ramada Limited Mount Sterling

Best Western Paris Inn

2.5 star property
7.8 out of 10, Good, (285)
"It was great. Very friendly staff "
The price is AED 375
AED 413 total
includes taxes & fees
25 Mar - 26 Mar
Best Western Paris Inn

Clarion Pointe Richmond North near University

2.5 star property
8.4 out of 10, Very Good, (714)
"Stayed the night during a road trip. Clean. Safe. Comfortable. "
The price is AED 281
AED 310 total
includes taxes & fees
30 Mar - 31 Mar
Clarion Pointe Richmond North near University

Motel 6 Richmond, KY – EKU Campus Area

2.0 star property
7.2 out of 10, Good, (62)
"The rooms have exterior entry doorways so you do hear the outside traffic. The heater was a little rattley but not to the point that it annoyed us and it worked very well. The room was clean and comfortable. No roaches or bedbugs. Plenty of hot water for the shower. Room also came with a microwave and mini fridge which was nice. It isnt fancy at all but it is affordable and the conditions were nuce for the price. There was no shampoo in room but when i went to front they did have some for...
The price is AED 231
AED 255 total
includes taxes & fees
25 Mar - 26 Mar
Motel 6 Richmond, KY – EKU Campus Area

Red Roof Inn Richmond, KY

2.5 star property
7.6 out of 10, Good, (994)
"The stay was good for a one night stop. It was a half way stop to break up a long drive so I wasn’t there to use the pool or anything. Room was very clean and comfy. Did not see what the breakfast was; I left to early. The location is right off highway and staff was very friendly. "
The price is AED 234
AED 258 total
includes taxes & fees
30 Mar - 31 Mar
Red Roof Inn Richmond, KY

Super 8 by Wyndham Richmond

2.0 star property
7.6 out of 10, Good, (859)
"Great place for an overnight stay. Convenient to highway, shopping and dining. "
The price is AED 247
AED 272 total
includes taxes & fees
25 Mar - 26 Mar
Super 8 by Wyndham Richmond

Best Western Richmond Hotel

2.5 star property
7.2 out of 10, Good, (1001)
"Room was clean and nicely remodeled, staff was very friendly and helpful."
The price is AED 290
AED 320 total
includes taxes & fees
10 Apr - 11 Apr
Best Western Richmond Hotel

Days Inn by Wyndham Richmond

2.0 star property
5.6 out of 10, (279)
"So this particular hotel is one of the cheapest rates and more reasonable stay for long term renters. They actually have pretty decent weekly rates. The breakfast wasn't anything fancy but it was the thought that counts that someone does get up at 5am and brew fresh coffee , fresh fruit and milk and juice . Nice sweet simple breakfast. I love that they have a in site laundry room. I like the privacy too. It's quiet and peaceful and the maids do not bother you when your checking out even if...
The price is AED 181
AED 200 total
includes taxes & fees
31 Mar - 1 Apr
Days Inn by Wyndham Richmond

Quality Inn Richmond

2.5 star property
8.8 out of 10, Excellent, (1005)
"Very nice and clean property. "
The price is AED 400
AED 441 total
includes taxes & fees
25 Mar - 26 Mar
Quality Inn Richmond

Holiday Inn Express & Suites Richmond by IHG

2.5 star property
9.0 out of 10, Wonderful, (843)
"The property was very clean and lots of restaurant options nearby. "
The price is AED 433
AED 478 total
includes taxes & fees
6 Apr - 7 Apr
Holiday Inn Express & Suites Richmond by IHG

Hampton Inn Richmond

2.5 star property
9.2 out of 10, Wonderful, (1002)
"Nice hotel. Updated, clean comfortable. Staff very polite and helpful."
The price is AED 372
AED 410 total
includes taxes & fees
13 Apr - 14 Apr
Hampton 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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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?

Spacious 5-bedroom House, Garage/Hot Tub/Bar, Close to RRG, Fiber WiFi: This vacation home rental outside of Winchester offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and a hot tub. 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?

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

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 Stays by OYO I-64 and Red Roof Winchester - Lexington East. 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. Other choices that feature an onsite pool include Hampton Inn Winchester and Best Western Winchester Hotel. 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 21 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.