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Find hotels in Winchester, KY from AED 190

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Compare 1,146 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Value Stay

2.0 star property
8.0 out of 10, Very Good, (87)
"Nice clean place"
The price is AED 217
AED 239 total
includes taxes & fees
6 Aug - 7 Aug
Value Stay

Best Western Winchester Hotel

2.5 star property
8.4 out of 10, Very Good, (957)
"Great one night stay. Pool area exceeded expectations!"
The price is AED 331
AED 364 total
includes taxes & fees
7 Aug - 8 Aug
Best Western Winchester Hotel

Holiday Inn Express Lexington East - Winchester by IHG

2.5 star property
9.4 out of 10, Exceptional, (473)
"Great staff - very friendly!"
The price is AED 378
AED 417 total
includes taxes & fees
31 Aug - 1 Sep
Holiday Inn Express Lexington East - Winchester by IHG

Baymont by Wyndham Winchester

2.5 star property
7.2 out of 10, Good, (733)
"Very nice hotel. Staff was wonderful. "
The price is AED 293
AED 323 total
includes taxes & fees
17 Aug - 18 Aug
Baymont by Wyndham Winchester

Comfort Inn

2.5 star property
7.0 out of 10, Good, (339)
"Hotel was overbooked. We had booked 2 rooms for my wife and 4 kids. Because there were no adjoining rooms we ended up booking just one room. It worked out ok but kind of disappointed."
The price is AED 256
AED 282 total
includes taxes & fees
31 Aug - 1 Sep
Comfort Inn

Red Roof Winchester - Lexington East

2.0 star property
6.4 out of 10, (566)
"Staff were really friendly, dog stay free, and the rooms were beautiful"
The price is AED 229
AED 252 total
includes taxes & fees
10 Aug - 11 Aug
Red Roof Winchester - Lexington East

Hampton Inn Winchester

2.5 star property
9.2 out of 10, Wonderful, (434)
"Property was nice"
The price is AED 425
AED 468 total
includes taxes & fees
31 Aug - 1 Sep
Hampton Inn Winchester

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1650)
"Very convenient and beautiful views! "
Natural Bridge State Resort Park

Black Bear Lodge Motel

2.5 star property
8.2 out of 10, Very Good, (575)
"Great stay!"
The price is AED 312
AED 344 total
includes taxes & fees
7 Aug - 8 Aug
Black Bear Lodge Motel

Comfort Inn and Suites

2.5 star property
7.6 out of 10, Good, (647)
"It was okay, but we chose it mainly because they are pet friendly."
The price is AED 338
AED 372 total
includes taxes & fees
4 Sep - 5 Sep
Comfort Inn and Suites

Ramada Limited Mount Sterling

2.0 star property
7.0 out of 10, Good, (721)
"Jaccuzzi in room, nice staff, and nice rooms."
The price is AED 290
AED 320 total
includes taxes & fees
3 Sep - 4 Sep
Ramada Limited Mount Sterling

Best Western Paris Inn

2.5 star property
7.8 out of 10, Good, (311)
"Handy to purchasing what you needed"
The price is AED 375
AED 413 total
includes taxes & fees
6 Aug - 7 Aug
Best Western Paris Inn

Clarion Pointe Richmond North near University

2.5 star property
8.4 out of 10, Very Good, (821)
"Amazing experience. One of my favourite places on the road so far"
The price is AED 262
AED 289 total
includes taxes & fees
1 Sep - 2 Sep
Clarion Pointe Richmond North near University

Motel 6 Richmond, KY – EKU Campus Area

2.0 star property
7.2 out of 10, Good, (76)
"Very basic hotel, but very clean and the bed was very comfortable."
The price is AED 231
AED 255 total
includes taxes & fees
11 Aug - 12 Aug
Motel 6 Richmond, KY – EKU Campus Area

Red Roof Inn Richmond, KY

2.5 star property
7.6 out of 10, Good, (1003)
"Had a good stay"
The price is AED 248
AED 273 total
includes taxes & fees
17 Aug - 18 Aug
Red Roof Inn Richmond, KY

Super 8 by Wyndham Richmond

2.0 star property
7.6 out of 10, Good, (924)
"It’s clean, and affordable and when you’re looking for a room that’s all that matters!"
The price is AED 206
AED 227 total
includes taxes & fees
6 Aug - 7 Aug
Super 8 by Wyndham Richmond

Best Western Richmond Hotel

2.5 star property
7.2 out of 10, Good, (1002)
"They are undergoing renovations which is clearly stated when you check in. The floors are beautiful and can tell it will be amazing when completed "
The price is AED 287
AED 317 total
includes taxes & fees
17 Aug - 18 Aug
Best Western Richmond Hotel

Days Inn by Wyndham Richmond

2.0 star property
5.6 out of 10, (306)
"Nice good place to rest comfortably bed’s friendly staff"
The price is AED 190
AED 210 total
includes taxes & fees
6 Aug - 7 Aug
Days Inn by Wyndham Richmond

Quality Inn Richmond

2.5 star property
8.8 out of 10, Excellent, (1006)
"good beds , great breakfast "
The price is AED 331
AED 365 total
includes taxes & fees
1 Sep - 2 Sep
Quality Inn Richmond

Comfort Suites Richmond

2.5 star property
7.6 out of 10, Good, (692)
"Staff was very nice and accommodating"
The price is AED 308
AED 340 total
includes taxes & fees
1 Sep - 2 Sep
Comfort Suites 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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Stay near popular Winchester attractions

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.

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

Top Winchester Hotel Reviews

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 Stay 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?

WiFi, Hot Tub, Pets, Prime Location in Red River Gorge!: This vacation home rental outside of Winchester is located in the mountains and has a selection of games, a hot tub, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. 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.

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 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'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 21 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 Lykins Park, College Park, and GRCHS Baseball Field. A couple of additional sights to add to your agenda are Southwind Golf Course and Clark County Public Library. 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.