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Winchester Hotels

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Top 10 trending Winchester hotels

Value Stay

2.0 star property
8.0 out of 10, Very Good, (87)
"Nice clean place"
The price is P3,385
P3,731 total
includes taxes & fees
Aug 10 - Aug 11
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 P5,188
P5,719 total
includes taxes & fees
Aug 7 - Aug 8
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 P5,938
P6,546 total
includes taxes & fees
Aug 31 - Sep 1
Holiday Inn Express Lexington East - Winchester by IHG

Baymont by Wyndham Winchester

2.5 star property
7.2 out of 10, Good, (733)
"Easy to get to. Clean staff were good"
The price is P4,578
P5,047 total
includes taxes & fees
Aug 17 - Aug 18
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 P4,347
P4,792 total
includes taxes & fees
Aug 26 - Aug 27
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 P3,574
P3,940 total
includes taxes & fees
Aug 11 - Aug 12
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 P7,575
P8,351 total
includes taxes & fees
Aug 31 - Sep 1
Hampton Inn Winchester

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1651)
"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 P4,876
P5,375 total
includes taxes & fees
Aug 11 - Aug 12
Black Bear Lodge Motel

Comfort Inn and Suites

2.5 star property
7.6 out of 10, Good, (648)
"It was okay, but we chose it mainly because they are pet friendly."
The price is P5,297
P5,840 total
includes taxes & fees
Sep 4 - Sep 5
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 P4,557
P5,024 total
includes taxes & fees
Sep 3 - Sep 4
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 P5,851
P6,450 total
includes taxes & fees
Aug 7 - Aug 8
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 P4,116
P4,538 total
includes taxes & fees
Sep 1 - Sep 2
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 P3,613
P3,983 total
includes taxes & fees
Aug 11 - Aug 12
Motel 6 Richmond, KY – EKU Campus Area

Red Roof Inn Richmond, KY

2.5 star property
7.6 out of 10, Good, (1000)
"Had a good stay"
The price is P3,869
P4,265 total
includes taxes & fees
Aug 17 - Aug 18
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 P3,228
P3,559 total
includes taxes & fees
Aug 7 - Aug 8
Super 8 by Wyndham Richmond

Best Western Richmond Hotel

2.5 star property
7.2 out of 10, Good, (1000)
"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 P4,485
P4,945 total
includes taxes & fees
Aug 26 - Aug 27
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 P2,974
P3,279 total
includes taxes & fees
Aug 14 - Aug 15
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 P5,203
P5,736 total
includes taxes & fees
Sep 1 - Sep 2
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 P5,339
P5,886 total
includes taxes & fees
Aug 17 - Aug 18
Comfort Suites Richmond
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Near an Attraction

Rupp Arena

Rupp Arena

Catch an event at Rupp Arena, and enjoy other activities in Lexington such as horseback riding. Attend a sporting event or simply enjoy the lively bars while you're in the area.

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.

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.

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 on a budget in Winchester?

Based on reviews, Red Roof Inn Lexington - Winchester is a popular hotel for our travelers who want a more economical choice, and features free WiFi and free parking. View all budget hotels in Winchester.

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 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's the best golf hotel in Winchester?

House on Belmont is a B&B featuring free breakfast and laundry facilities, and it's a top choice for golfing nearby. Visit Southwind Golf Course or Cassell Creek Golf Course to perfect your golf swing. See more golf hotels in Winchester.

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 is the best spa hotel in Winchester?

Baymont by Wyndham Winchester is a top spa hotel featuring a pool and a fitness center. See all spa hotels 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 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.