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Find hotels in Winchester, KY from AED 169

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Compare 1,091 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, (434)
"Friendly staff clean rooms and great breakfast. Pool was nice "
The price is AED 382
AED 425 total
includes taxes & fees
16 Mar - 17 Mar
Holiday Inn Express Lexington East - Winchester by IHG

Baymont by Wyndham Winchester

2.5 star property
7.0 out of 10, Good, (649)
"The Baymont has the potential to get five stars. It's clean the staff was nice. The rooms are of the time period except the bathrooms. Very dated and not what you see in the picture. With that said the shower head sprayed everywhere but the water was hot! Beds were comfy as were the pillows. We always turn the air all the way down and stayed warm under the covers. Breakfast it's free, you can't complain about free. We didn't use the pool but it looked well maintained. The property just sits in a...
The price is AED 248
AED 273 total
includes taxes & fees
16 Mar - 17 Mar
Baymont by Wyndham Winchester

Best Western Winchester Hotel

2.5 star property
8.4 out of 10, Very Good, (896)
"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
14 Mar - 15 Mar
Best Western Winchester Hotel

Hampton Inn Winchester

2.5 star property
9.2 out of 10, Wonderful, (412)
"Close to town. "
The price is AED 445
AED 491 total
includes taxes & fees
16 Mar - 17 Mar
Hampton Inn 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
20 Mar - 21 Mar
Value Stays by OYO I-64

Red Roof Winchester - Lexington East

2.0 star property
6.4 out of 10, (541)
"Property could use a up grade but the room was really clean the staff was really nice and helpful I would stay here again. The price was great "
The price is AED 208
AED 229 total
includes taxes & fees
17 Mar - 18 Mar
Red Roof Winchester - Lexington East

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1503)
"2nd year here and love it!"
The price is AED 407
AED 449 total
includes taxes & fees
16 Mar - 17 Mar
Natural Bridge State Resort Park

Black Bear Lodge Motel

2.5 star property
8.2 out of 10, Very Good, (489)
"Room was great and had incredibly easy access to everything you would want to see in the area! The only unfortunate part was that the walls were very thin and not very soundproof, so we were woken up at all hours of the night from noisy neighbors. Other than that, the place was great! Rooms were clean and appeared exactly as described, would recommend to others."
The price is AED 312
AED 344 total
includes taxes & fees
16 Mar - 17 Mar
Black Bear Lodge Motel

Comfort Inn and Suites

2.5 star property
7.6 out of 10, Good, (581)
"Room was clean close to restaurants safe area "
The price is AED 288
AED 317 total
includes taxes & fees
30 Mar - 31 Mar
Comfort Inn and Suites

Ramada Limited Mount Sterling

2.0 star property
6.8 out of 10, (642)
"The hot tub not working 😞"
The price is AED 293
AED 323 total
includes taxes & fees
16 Mar - 17 Mar
Ramada Limited Mount Sterling

Holiday Inn Express & Suites Mt Sterling North by IHG

2.5 star property
9.0 out of 10, Wonderful, (498)
"Close to a lot things "
The price is AED 382
AED 421 total
includes taxes & fees
23 Mar - 24 Mar
Holiday Inn Express & Suites Mt Sterling North by IHG

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
16 Mar - 17 Mar
Best Western Paris Inn

Clarion Pointe Richmond North near University

2.5 star property
8.4 out of 10, Very Good, (706)
"Rooms were OK, although the beds were too hard. Need instructions on how to turn on/off shower head. Room was clean and staff were pleasant. Bathrooms need a make-over - too small. "
The price is AED 281
AED 310 total
includes taxes & fees
24 Mar - 25 Mar
Clarion Pointe Richmond North near University

Red Roof Inn Richmond, KY

2.5 star property
7.6 out of 10, Good, (990)
"Nice location"
The price is AED 223
AED 246 total
includes taxes & fees
19 Mar - 20 Mar
Red Roof Inn Richmond, KY

Super 8 by Wyndham Richmond

2.0 star property
7.6 out of 10, Good, (854)
"Very accessible off of Interstate and Cracker Barrel nearby. What more could you ask for. Very pleasant front desk experience at check-in."
The price is AED 206
AED 227 total
includes taxes & fees
14 Mar - 15 Mar
Super 8 by Wyndham Richmond

Best Western Richmond Hotel

2.5 star property
7.2 out of 10, Good, (1002)
"Nice room and excellent staff. The breakfast was excellent 👌 There was a wedding party downstairs that was loud and went on most of the night."
The price is AED 287
AED 317 total
includes taxes & fees
26 Mar - 27 Mar
Best Western Richmond Hotel

Quality Inn Richmond

2.5 star property
8.8 out of 10, Excellent, (1002)
"Excellent hotel. Just off the expressway with plenty of places to eat nearby."
The price is AED 323
AED 356 total
includes taxes & fees
2 Apr - 3 Apr
Quality Inn Richmond

Holiday Inn Express & Suites Richmond by IHG

2.5 star property
9.0 out of 10, Wonderful, (840)
"We were very happy with our stay! Breakfast choices were good plentiful each day! Restaurants and fast food options within walking or short drive. Still I wish hotel or expedia would adjusted my rate charges to the lower rates I heard on check-in. "
The price is AED 411
AED 453 total
includes taxes & fees
30 Mar - 31 Mar
Holiday Inn Express & Suites Richmond by IHG

Hampton Inn Richmond

2.5 star property
9.2 out of 10, Wonderful, (1001)
"Very nice experience."
The price is AED 371
AED 410 total
includes taxes & fees
2 Apr - 3 Apr
Hampton Inn Richmond

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

2.5 star property
8.6 out of 10, Excellent, (1372)
"Love the Queen suite "
The price is AED 332
AED 401 total
includes taxes & fees
16 Mar - 17 Mar
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
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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Canoeing down the Kentucky river 🚣
Photo by Hyelsinta
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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. A top sight in the area is Kentucky Horse Park. In Winchester, there are 19 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.