Photo by Nawa Aseen

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Top hotels and accommodation in Winchester

In-room safe, desk, laptop workspace, blackout curtains
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, (522)
"Hotel was clean and comfortable"
United States
Lara
Travelling with family
The price is AU$146
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express Lexington East - Winchester by IHG
Suite, 1 King Bed, Non Smoking
Hampton Inn Winchester

Hampton Inn Winchester

2.5 star property
Winchester
9.2 out of 10, Wonderful, (450)
"Room and bed were nice and bathtub extra wide with grab bar."
United States
Marie
Travelling for business
The price is AU$185
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn Winchester
Seasonal outdoor pool
Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 star property
Winchester
8.4 out of 10, Very good, (1001)
"Firm bed, clean room, friendly staff and adequate breakfast."
United States
Barbara
Travelling with partner
The price is AU$148
includes taxes & fees
11 Dec - 12 Dec
Best Western Winchester Hotel
Lobby
Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

2.5 star property
Winchester
7.2 out of 10, Good, (770)
"the beds were clean and acceptable"
United States
Kelly
The price is AU$132
includes taxes & fees
17 Dec - 18 Dec
Baymont by Wyndham Winchester
Desk, iron/ironing board, free WiFi, bed sheets
Comfort Inn Winchester

Comfort Inn Winchester

2.5 star property
Winchester
7.0 out of 10, Good, (352)
"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 AU$103
includes taxes & fees
28 Dec - 29 Dec
Comfort Inn Winchester
Exterior
Value Stay

Value Stay

2.0 star property
Winchester
7.8 out of 10, Good, (124)
"Good clean room for the money"
United States
Darrel L
Travelling for leisure
The price is AU$105
includes taxes & fees
7 Dec - 8 Dec
Value Stay
Exterior
Red Roof Inn Winchester - Lexington East

Red Roof Inn Winchester - Lexington East

2.0 star property
Winchester
6.4 out of 10, (585)
"Great stay"
United States
Walter
The price is AU$103
includes taxes & fees
10 Dec - 11 Dec
Red Roof Inn Winchester - Lexington East
Exterior
Staybridge Suites Lexington S Medical Ctr Area by IHG

Staybridge Suites Lexington S Medical Ctr Area by IHG

3.0 star property
Lexington
9.6 out of 10, Exceptional, (485)
"The room itself was beautiful."
United States
Angeline
Travelling with family
The price is AU$170
includes taxes & fees
1 Jan - 2 Jan 2026
Staybridge Suites Lexington S Medical Ctr Area by IHG
Property amenity
Candlewood Suites Lexington Medical District by IHG

Candlewood Suites Lexington Medical District by IHG

2.5 star property
South Broadway Park
9.2 out of 10, Wonderful, (793)
"Hotel was super clean, fancy"
United States
Autumn
Travelling for leisure
The price is AU$136
includes taxes & fees
14 Dec - 15 Dec
Candlewood Suites Lexington Medical District by IHG
Exterior
Holiday Inn Express Hotel & Suites Lexington-Downtown by IHG

Holiday Inn Express Hotel & Suites Lexington-Downtown by IHG

2.5 star property
South Broadway Park
8.8 out of 10, Excellent, (1003)
"The beds and pillows were very comfortable."
United States
Kelly
Travelling with partner
The price is AU$150
includes taxes & fees
23 Dec - 24 Dec
Holiday Inn Express Hotel & Suites Lexington-Downtown by IHG
Lobby
Hyatt Place Lexington

Hyatt Place Lexington

3.0 star property
Lexington
8.8 out of 10, Excellent, (1005)
"Great pool, clean rooms, quick and easy check in."
United States
Joshua
Travelling with small children
The price is AU$177
includes taxes & fees
9 Dec - 10 Dec
Hyatt Place Lexington
Exterior
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, (1003)
"Hotel is very quiet and clean and great for an overnight stay."
United States
Lisa Valerie
Travelling solo
The price is AU$138
includes taxes & fees
5 Jan - 6 Jan 2026
Country Inn & Suites by Radisson, Georgetown, KY
Lobby
Hilton Lexington/Downtown

Hilton Lexington/Downtown

3.5 star property
Downtown Lexington
8.4 out of 10, Very good, (1006)
"Room and access to Rupp Arena were excellent."
United States
Heather
Travelling with family
The price is AU$214
includes taxes & fees
23 Dec - 24 Dec
Hilton Lexington/Downtown
Exterior
Quality Inn Richmond

Quality Inn Richmond

2.5 star property
Richmond
9.0 out of 10, Wonderful, (1001)
"The room as well as the lobby and breakfast area were all very clean and well kept."
United States
Susan
The price is AU$156
includes taxes & fees
7 Dec - 8 Dec
Quality Inn Richmond
Terrace/patio
Home2 Suites by Hilton Lexington Hamburg

Home2 Suites by Hilton Lexington Hamburg

3.0 star property
Lexington
9.2 out of 10, Wonderful, (1002)
"Very nice clean room and super friendly staff."
United States
Mekesha
Travelling with friends
The price is AU$166
includes taxes & fees
13 Dec - 14 Dec
Home2 Suites by Hilton Lexington Hamburg
Exterior
Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG

3.0 star property
Lexington
9.0 out of 10, Wonderful, (1002)
"Hotel Sushi restaurant was excellent"
United States
Shayne
The price is AU$147
includes taxes & fees
19 Dec - 20 Dec
Holiday Inn Lexington - Hamburg by IHG
Exterior
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, (871)
"Bed was very comfortable with the promise of a good sleep."
United States
Claudette
The price is AU$133
includes taxes & fees
28 Dec - 29 Dec
avid hotel Lexington - Hamburg Area by IHG
Free daily continental breakfast
Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg

2.5 star property
Lexington
8.6 out of 10, Excellent, (268)
"Nice location, though being renovated, lots of dining options close by."
United States
Melody
Travelling with family
The price is AU$103
includes taxes & fees
14 Dec - 15 Dec
Spark by Hilton Lexington Hamburg
Lobby
Hyatt Regency Lexington

Hyatt Regency Lexington

3.5 star property
Downtown Lexington
8.6 out of 10, Excellent, (1002)
"Beds so comfy the down pillows and comforter were great."
United States
Jimmye
Travelling for leisure
The price is AU$187
includes taxes & fees
26 Dec - 27 Dec
Hyatt Regency Lexington
Exterior
Holiday Inn Express & Suites Richmond by IHG

Holiday Inn Express & Suites Richmond by IHG

2.5 star property
Richmond
9.0 out of 10, Wonderful, (908)
"Hotel was very clean and quiet"
Canada
G
Travelling for leisure
The price is AU$143
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express & Suites Richmond by IHG
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

Explore the great outdoors at Winchester Traveling Trail, a lovely green space in Winchester. You can enjoy the restaurants while in the area.
See properties

Cassell Creek Golf Course

Play a round of golf in Winchester at Cassell Creek Golf Course, and enjoy other activities such as horse riding. Savour the top-notch restaurants and cosy cafes while in town.
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

Recent Reviews in Winchester

The Manchester

The Manchester

10/10 Excellent
"Room was more beautiful in person."
syliesha 4-night trip
Posted 4 days ago
The Manchester

More cheap accommodation in Winchester

Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park

1938 Stanton Way Lexington KY
The price is AU$112 per night from 22 Dec to 23 Dec
AU$112
22 Dec - 23 Dec
includes taxes & fees
8.2/10 Very Good! (1,637 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 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?
Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location: This holiday home rental outside of Winchester is located in the city centre, and has a fireplace, a patio and air conditioning 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. 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 Baymont by Wyndham Winchester and Value Stay. 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 19 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 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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