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Our top choices for Winchester hotels

Value Stay

Value Stay
2.0 star property
Winchester
7.8 out of 10, Good, (134 reviews)
"Don't let the outside fool you. My room was super clean with brand new appliances..Fast and easy check in, staff was polite. If your looking for a cheap room just to lay your head down you can't go wrong here."
United States
Gary
The price is NZ$110
includes taxes & fees
7 Apr - 8 Apr
Value Stay

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (783 reviews)
"Great place for a reasonable price! "
United States
Whitney
The price is NZ$146
includes taxes & fees
7 Apr - 8 Apr
Baymont by Wyndham Winchester

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very good, (1,001 reviews)
"Room was fine. Fairly clean. King size bed was old."
United States
Heather
The price is NZ$174
includes taxes & fees
7 Apr - 8 Apr
Best Western Winchester Hotel

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (460 reviews)
"Clean area all around. Second time staying there. I would stay again for sure. "
United States
Cody
The price is NZ$234
includes taxes & fees
19 Apr - 20 Apr
Hampton Inn Winchester

Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
2.5 star property
Winchester
9.2 out of 10, Wonderful, (557 reviews)
"Clean room, great hot fresh breakfast "
United States
Bob
The price is NZ$242
includes taxes & fees
6 May - 7 May
Holiday Inn Express Lexington East - Winchester by IHG

Red Roof Inn Winchester - Lexington East

Red Roof Inn Winchester - Lexington East
2.0 star property
Winchester
6.4 out of 10, (593 reviews)
"Great workers showed us plenty respect clean as a whistle would recommend to anybody"
United States
Kimberly
The price is NZ$130
includes taxes & fees
10 Apr - 11 Apr
Red Roof Inn Winchester - Lexington East

Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (358 reviews)
"Very nice "
United States
Ronald
The price is NZ$145
includes taxes & fees
3 May - 4 May
Comfort Inn Winchester

Super 8 by Wyndham Richmond

Super 8 by Wyndham Richmond
2.0 star property
Richmond
7.8 out of 10, Good, (1,002 reviews)
"Staff was extremely friendly at check in and check out, and we had a fine stay for a quick overnight "
United States
Laura
The price is NZ$107
includes taxes & fees
15 Apr - 16 Apr
Super 8 by Wyndham Richmond

Holiday Inn Express Lexington Horse Park Area by IHG

Holiday Inn Express Lexington Horse Park Area by IHG
3.0 star property
Lexington
9.4 out of 10, Exceptional, (2,187 reviews)
"Great location and staff. "
United States
Melissa
The price is NZ$218
includes taxes & fees
14 Apr - 15 Apr
Holiday Inn Express Lexington Horse Park Area by IHG

Home2 Suites By Hilton Richmond, Ky

Home2 Suites By Hilton Richmond, Ky
3.0 star property
Richmond
9.6 out of 10, Exceptional, (203 reviews)
"Great place to stay close to everything "
United States
Jeannette
The price is NZ$189
includes taxes & fees
13 Apr - 14 Apr
Home2 Suites By Hilton Richmond, Ky

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,841 reviews)
"What a great staff Very clean, friendly hotel Def will stay again"
United States
Loreli
The price is NZ$202
includes taxes & fees
12 Apr - 13 Apr
Natural Bridge State Resort Park

Black Bear Lodge Motel

Black Bear Lodge Motel
2.5 star property
Slade
8.0 out of 10, Very good, (645 reviews)
"We have stayed here before. It is affordable, the staff is great (I accidently reserved the wrong dates and they were able to fix it and accommodate me on the dates I needed) The area was quiet on this trip as it was out of season. "
United States
Connie
The price is NZ$170
includes taxes & fees
8 Apr - 9 Apr
Black Bear Lodge Motel

Quality Inn Richmond

Quality Inn Richmond
2.5 star property
Richmond
9.0 out of 10, Wonderful, (1,007 reviews)
"Great stay."
United States
Matthew
The price is NZ$192
includes taxes & fees
7 Apr - 8 Apr
Quality Inn Richmond

Hampton Inn Richmond

Hampton Inn Richmond
2.5 star property
Richmond
9.2 out of 10, Wonderful, (1,006 reviews)
"Wonderful staff, breakfast was great and the room was awesome. "
United States
Cara
The price is NZ$221
includes taxes & fees
13 Apr - 14 Apr
Hampton Inn Richmond

Baymont by Wyndham Richmond KY

Baymont by Wyndham Richmond KY
2.5 star property
Richmond
7.0 out of 10, Good, (1,006 reviews)
"Overall a good stay. Staff was very friendly and helpful "
United States
Wayne
The price is NZ$137
includes taxes & fees
13 Apr - 14 Apr
Baymont by Wyndham Richmond KY

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
3.0 star property
Lexington
8.8 out of 10, Excellent, (1,151 reviews)
"A very well run hotel."
United States
Janice
The price is NZ$195
includes taxes & fees
12 Apr - 13 Apr
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

Days Inn Lexington SE/Hamburg

Days Inn Lexington SE/Hamburg
2.0 star property
Lexington
7.2 out of 10, Good, (1,004 reviews)
"Great price and a nice place to stay"
United States
Saelim
The price is NZ$117
includes taxes & fees
19 Apr - 20 Apr
Days Inn Lexington SE/Hamburg

Comfort Inn & Suites Mount Sterling

Comfort Inn & Suites Mount Sterling
2.5 star property
Mount Sterling
7.8 out of 10, Good, (730 reviews)
"Room was very clean, check in was a breeze. "
United States
Emily
The price is NZ$161
includes taxes & fees
27 Apr - 28 Apr
Comfort Inn & Suites Mount Sterling

Country Inn & Suites by Radisson, Georgetown, KY

Country Inn & Suites by Radisson, Georgetown, KY
3.0 star property
Georgetown
8.8 out of 10, Excellent, (1,006 reviews)
"Nice clean room, the staff were wonderful. "
United States
Jay
The price is NZ$174
includes taxes & fees
3 May - 4 May
Country Inn & Suites by Radisson, Georgetown, KY

Asbury Inn & Suites

Asbury Inn & Suites
3.0 star property
Wilmore
9.6 out of 10, Exceptional, (496 reviews)
"We love the Asbury Inn! The rooms are lovely and clean and the breakfast is delicious! "
United States
Hannah
The price is NZ$250
includes taxes & fees
7 Apr - 8 Apr
Asbury Inn & Suites
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 city centre 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.

MAY 9, 2023 - WINCHESTER, KENTUCKY - aerial view of historic small town of Winchester with Town Clocktower and historic storefronts and buildings

Top Winchester Hotel Reviews

More cheap accommodation in Winchester

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 Best Western Winchester Hotel as top options for your visit. See all available top hotels, or vacation rentals in Winchester.
What are some of the best holiday rentals that Winchester has to offer?
Hot Tub! Fire pit! Picnic area & Grill! View Hardwicks Creek Haven@RRG: This holiday home rental outside of Winchester is located in a rural location, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub. See all vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes! You'll find that most hotel room reservations are fully refundable if cancelled before the accommodation's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a reservation that's non-refundable, you may still be able to cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
What's the best family accommodation in Winchester?
Hampton Inn Winchester is a hotel with free parking and free breakfast, and it's a top choice on Expedia for families. Also, attractions in the area such as Lexington Ice Center and Paradise Cove Aquatic Center are fun for children of all ages. Find more child-friendly accommodations in Winchester.
What is the top 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 Wi-Fi. Hampton Inn Winchester and Red Roof Winchester - Lexington East are two other good options for your holiday. See all available hotels listed as LGBTQ-friendly in Winchester.
What's the best dog-friendly accommodation option in Winchester?
Baymont by Wyndham Winchester is a top dog-friendly hotel, and offers an indoor pool and a fitness centre for its human guests. Other good options to stay with your pet include Fantastic 4-bedroom farmhouse with AC in charming Winchester and Best Western Winchester Hotel. See more pet-friendly hotel accommodations in Winchester.
What are some accommodation options 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 another choice with an on-site pool. View all hotels with pools in Winchester.
What's the most popular hotel in Winchester with an on-site water park or a water park nearby?
Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min. is a favourite water park hotel in Winchester
How is it to stay in Winchester?
Visitors to Winchester will definitely enjoy the restaurants. Tourists can also enjoy the city's coffee shops, shopping and football games. In Winchester, there are 21 hotels and other accommodation options to choose from. Find out more about Winchester.
What should I do while I'm visiting Winchester?
Landmarks like Bluegrass Heritage Museum, Winchester Opera House and Clark County Courthouse might be worth a visit. Natural beauty is on display at Winchester Traveling Trail, Lykins Park and College Park. A couple of additional sights to add to your itinerary are Cassell Creek Golf Course and Clark County Public Library. Take a look at what more there is to see and do in Expedia's Winchester guide.
What's the weather like in Winchester?
The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Winchester is 1426 mm.

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