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Our top choices for Winchester hotels

In-room safe, desk, laptop workspace, blackout curtains
Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
2.5 star property
Winchester
9.4 out of 10, Exceptional, (530)
This business-friendly hotel offers complimentary breakfast, WiFi, and parking. Enjoy a refreshing dip in the indoor pool or visit the 24-hour fitness centre. Located near Community Park with helpful staff ready to enhance your stay.
"The room was clean, bed was very comfortable and the staff couldn’t have been nicer!"
United States
Stevy
The price is NZ$185
includes taxes & fees
19 Jan - 20 Jan
Holiday Inn Express Lexington East - Winchester by IHG
Seasonal outdoor pool
Best Western Winchester Hotel

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very good, (1000)
Wake up to a complimentary full breakfast at this tranquil Winchester hotel, where the helpful staff receives consistent praise from travellers. Enjoy free parking and easy access to Wiseman Park and Community Park, plus a refreshing seasonal outdoor pool.
"Clean room, friendly and fast check in service and had a great nights sleep "
United States
Cynthia
The price is NZ$138
includes taxes & fees
15 Jan - 16 Jan
Best Western Winchester Hotel
Suite, 1 King Bed, Non Smoking
Hampton Inn Winchester

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (454)
This quiet hotel offers safe lodgings, complimentary breakfast, free WiFi, and parking. Fitness fans can enjoy the on-site gym. The clean rooms and friendly staff create a comfortable stay, with Lykins Park and The Holler nearby.
"Would stay there again"
United States
Patricia
The price is NZ$235
includes taxes & fees
25 Jan - 26 Jan
Hampton Inn Winchester
Lobby
Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (772)
Peaceful hotel in Winchester with a serene atmosphere, where guests can enjoy a refreshing dip in the indoor pool. Free breakfast, WiFi, and parking add value. The clean rooms and proximity to The Holler and Lykins Park make for a relaxing stay.
"The room was all that we expected very good. Staff was very friendly."
United States
LEROY
The price is NZ$152
includes taxes & fees
18 Jan - 19 Jan
Baymont by Wyndham Winchester
Desk, iron/ironing board, free WiFi, bed sheets
Comfort Inn Winchester

Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (353)
Travellers call this hotel quiet and restful. Jump into the indoor pool for a morning swim or hit the fitness centre. Community Park and Wiseman Park are nearby, with free WiFi and parking for convenience.
"The pool had no water. There was no pool available. There wasn't any hot water in our room. Unless you run it for 15/20 min"
United States
teresa
The price is NZ$140
includes taxes & fees
26 Jan - 27 Jan
Comfort Inn Winchester
Exterior
Value Stay

Value Stay

Value Stay
2.0 star property
Winchester
7.8 out of 10, Good, (127)
This convenient Winchester motel offers complimentary Wi-Fi and parking just minutes from Community Park and Wiseman Park. Enjoy 24-hour front desk service for any assistance needed during your stay.
"Awesome rooms and service"
United States
Brandon
The price is NZ$128
includes taxes & fees
18 Jan - 19 Jan
Value Stay
Exterior
Red Roof Inn Winchester - Lexington East

Red Roof Inn Winchester - Lexington East

Red Roof Inn Winchester - Lexington East
2.0 star property
Winchester
6.4 out of 10, (587)
Conveniently located in Winchester, this hotel offers free WiFi and parking, plus 24-hour front desk service. Explore nearby attractions like The Holler and Lykins Park, with easy access to Blue Grass Airport just 32 minutes away.
"Great stay"
United States
Walter
The price is NZ$119
includes taxes & fees
18 Jan - 19 Jan
Red Roof Inn Winchester - Lexington East
Lobby
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

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, (1207)
Escape to this quiet Lexington retreat with an indoor pool and fitness centre. Located near popular restaurants and a short drive from Rupp Arena, guests enjoy complimentary breakfast, WiFi, and parking for exceptional value.
"Love love love this hotel. "
United States
Kirsten
The price is NZ$181
includes taxes & fees
8 Jan - 9 Jan
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Exterior
avid hotel Lexington - Hamburg Area by IHG

avid hotel Lexington - Hamburg Area by IHG

avid hotel Lexington - Hamburg Area by IHG
2.5 star property
Lexington
9.2 out of 10, Wonderful, (881)
Located near Rupp Arena and University of Kentucky, this Lexington hotel offers a 24-hour fitness centre and complimentary on-the-go breakfast. Free WiFi and parking make exploring convenient, with Kroger Field just a short drive away.
"Great stay"
United States
Amy
The price is NZ$141
includes taxes & fees
30 Jan - 31 Jan
avid hotel Lexington - Hamburg Area by IHG
Free daily buffet breakfast
Hampton Inn I-75 Lexington/Hamburg Area

Hampton Inn I-75 Lexington/Hamburg Area

Hampton Inn I-75 Lexington/Hamburg Area
2.5 star property
Lexington
8.6 out of 10, Excellent, (971)
Enjoy peaceful accommodation with an indoor pool and fitness centre just minutes from Rupp Arena and University of Kentucky. Free breakfast, WiFi, and parking enhance your stay, while helpful staff ensure a clean, comfortable experience near major venues.
"Excellent motel "
Canada
David
The price is NZ$163
includes taxes & fees
16 Jan - 17 Jan
Hampton Inn I-75 Lexington/Hamburg Area
View from room
Natural Bridge State Resort Park

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1790)
Nestled in Slade, this cabin offers convenience to Natural Bridge State Park and Red River Gorge. Enjoy complimentary breakfast before exploring nearby attractions. The seasonal outdoor pool and Sandstone Arches Restaurant provide perfect relaxation after wilderness adventures.
"Front desk staff was super nice, room was perfect as we were hiking and needed a place to relax and get some sleep! "
United States
Kathy
Natural Bridge State Resort Park
Exterior
Holiday Inn Express & Suites Mt Sterling North by IHG

Holiday Inn Express & Suites Mt Sterling North by IHG

Holiday Inn Express & Suites Mt Sterling North by IHG
2.5 star property
Mount Sterling
8.8 out of 10, Excellent, (577)
This Mount Sterling hotel offers a refreshing indoor pool and 24-hour fitness centre. Enjoy free breakfast, WiFi, and parking, with Old Silo Golf Course and local library nearby. Guests praise the friendly, attentive staff.
"Room was super clean and the woman at the front desk was really nice and very helpful"
United States
mark
The price is NZ$170
includes taxes & fees
18 Jan - 19 Jan
Holiday Inn Express & Suites Mt Sterling North by IHG
Exterior
Quality Inn Richmond

Quality Inn Richmond

Quality Inn Richmond
2.5 star property
Richmond
9.0 out of 10, Wonderful, (1017)
Located near Richmond Centre Mall, this welcoming hotel offers a 24-hour fitness centre and outdoor pool. Guests appreciate the clean accommodation, helpful staff, and convenient amenities like free WiFi and parking.
"Friendly staff, clean room, easy check in and check out"
United States
Joelle
The price is NZ$170
includes taxes & fees
11 Jan - 12 Jan
Quality Inn Richmond
Exterior
Country Inn & Suites by Radisson, Georgetown, KY

Country Inn & Suites by Radisson, Georgetown, KY

Country Inn & Suites by Radisson, Georgetown, KY
3.0 star property
Georgetown
9.0 out of 10, Wonderful, (1006)
"Clean and comfortable traveler's hotel with a friendly staff."
United States
Joy
The price is NZ$149
includes taxes & fees
13 Jan - 14 Jan
Country Inn & Suites by Radisson, Georgetown, KY
Exterior
Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North
3.0 star property
Lexington
8.6 out of 10, Excellent, (1014)
"Perfect for overnight stay! Great breakfast "
Canada
Lawrence
The price is NZ$142
includes taxes & fees
18 Jan - 19 Jan
Fairfield Inn & Suites by Marriott Lexington North
Terrace/patio
Hampton Inn Nicholasville Brannon Crossing

Hampton Inn Nicholasville Brannon Crossing

Hampton Inn Nicholasville Brannon Crossing
2.5 star property
Nicholasville
9.4 out of 10, Exceptional, (245)
Nicholasville hotel with seasonal outdoor pool, just 10 minutes from University of Kentucky and Kroger Field. Red Mile Racetrack and Keeneland Racing Course are a short drive away. Enjoy free parking and buffet breakfast at this business-friendly spot with attentive staff.
"Very nice all around! Would stay again. "
United States
Dave
The price is NZ$170
includes taxes & fees
14 Jan - 15 Jan
Hampton Inn Nicholasville Brannon Crossing
Front of property
Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park
2.5 star property
Lexington
8.2 out of 10, Very good, (1643)
Experience peaceful sleep and relaxation minutes from the Kentucky Horse Park, Rupp Arena, and Kroger Field. This quiet Lexington hotel offers continental breakfast, complimentary WiFi and parking, plus a fitness centre. Guests rave about the comfortable beds and helpful staff.
"Easy check in, the staff was very friendly and helpful "
United States
Chris
The price is NZ$130
includes taxes & fees
25 Jan - 26 Jan
Quality Inn Lexington -Horse Park
Exterior
Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG
3.0 star property
Lexington
9.0 out of 10, Wonderful, (1003)
"Clean room, close to restaurants"
United States
andrea
The price is NZ$169
includes taxes & fees
30 Jan - 31 Jan
Holiday Inn Lexington - Hamburg by IHG
Indoor pool
Comfort Inn & Suites Mount Sterling

Comfort Inn & Suites Mount Sterling

Comfort Inn & Suites Mount Sterling
2.5 star property
Mount Sterling
7.8 out of 10, Good, (709)
Experience tranquil accommodation near Old Silo Golf Course. This business-friendly hotel offers a spa pool for relaxing after exploring Mount Sterling. Guests praise the helpful staff, clean rooms, and peaceful atmosphere.
"We stay here anytime we are in town "
United States
Donn
The price is NZ$149
includes taxes & fees
25 Jan - 26 Jan
Comfort Inn & Suites Mount Sterling
Lobby
Hampton Inn Richmond

Hampton Inn Richmond

Hampton Inn Richmond
2.5 star property
Richmond
9.2 out of 10, Wonderful, (1009)
Quiet sanctuary near Richmond Centre Mall with an indoor pool to revitalise after a day of exploration. Free breakfast, WiFi, and parking enhance your stay, while the fitness centre keeps your routine on track. Starbucks and petrol stations nearby.
"Room was clean, staff was great. Breakfast was good and well stocked"
United States
Roger
The price is NZ$187
includes taxes & fees
6 Feb - 7 Feb
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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Stay near popular Winchester attractions

Winchester Traveling Trail

This serene mile-long pathway winds through meadows of Kentucky bluegrass, offering a peaceful escape. Benches and shaded areas make it perfect for a leisurely morning stroll with your leashed dog.
See properties

Bluegrass Heritage Museum

This Romanesque Revival building houses three floors of exhibits chronicling the Bluegrass region's rich heritage. Explore the preserved historic operating room and discover local artefacts spanning centuries.
See properties

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.

See all hotels in Winchester
Thanks to my friend of mine who's recommended me to this spot easy hike short walk to get there
Photo by Nawa Aseen
Open Photo by Nawa Aseen

Top Winchester Hotel Reviews

Hyatt Regency Lexington

Hyatt Regency Lexington

10/10 Excellent
"Room was clean and everyone was very nice and helpful! Only issue we had were the pillows, they were terrible!"
Melissa 1-night trip
Posted 1 day ago
Hyatt Regency Lexington

More cheap accommodation in Winchester

Super 8 by Wyndham Georgetown

Super 8 by Wyndham Georgetown

250 Tiger Way Georgetown KY
The price is NZ$112 per night from 12 Jan to 13 Jan
NZ$112
12 Jan - 13 Jan
includes taxes & fees
8.2/10 Very Good! (1,000 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 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?
Morning View Ranch- Red River Gorge- Indoor Pool open March-Nov. Pet friendly.: This holiday home rental outside of Winchester is located on a river, and has an indoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. 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?
Best Western Winchester Hotel is a top hotel for people travelling with their pets, and offers a seasonal outdoor pool and a computer station for its human guests. Other good options to stay with your pet include Hampton Inn Winchester and Baymont by Wyndham Winchester. See more pet-friendly hotel accommodations in Winchester.
What are some accommodation options with pools in Winchester?
Best Western Winchester Hotel is a top hotel with a seasonal outdoor pool, free full breakfast and free self-parking. Baymont by Wyndham Winchester 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 20 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 College Park, GRCHS Baseball Field and Community Park. A couple of additional sights to add to your itinerary are Clark County Public Library and The Holler. 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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