Hotels in Winchester
The stock is mixed, with 3-star the largest single band at 58 of 117, and 3 of them are within a mile of the centre. Below are the closest properties to the middle of Winchester, nearest first, plus what is near each venue in the city — because if you are here for one event, distance from that building matters more than distance from downtown.
What the hotels in Winchester are like
Before the list, the shape of it. These figures cover every property the search found within about five miles of the middle of Winchester — not just the 36 shown below, which are simply the closest.
| Measure | Winchester | What it tells you |
|---|---|---|
| Properties found | 117 | Everything listed within about five miles of the centre. The 36 nearest are shown below. |
| Star mix | 30 × 4★, 58 × 3★, 15 × 2★, 1 × 1★ | 3-star is the largest band here. |
| Average guest score | 8.4/10 | Across the 99 rated properties. Supplied by our accommodation partner, not a StubOrder rating. |
| Within a mile of the centre | 3 of 117 | The rest are a drive or a transit ride. |
| Closest property | 0.7 mi | From the city’s centre point, in a straight line. |
Hotels in Winchester, closest to the centre first
Pick your dates to price these for the nights you actually want. Nothing is quoted until you do, because a nightly rate for the wrong dates is worse than no rate at all.
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Lexington Getaway w/ Backyard Deck < 2 Mi to UK!
206 Bassett Avenue, Lexington
Garden Views and Complimentary Wi-Fi Enjoy the serene garden views and stay connected with complimentary wireless internet access. Convenient Amenities Make yourself at home in th…
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Kathy's Place
146 North Ashland Avenue, Lexington
Convenient Amenities: Enjoy complimentary wireless internet access and barbecue grills during your stay. Benefit from free self parking on-site. Comfortable Accommodation: Relax i…
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LUX - Downtown Oasis - Pool Table! Free Parking!
433 Elm Tree Lane, Lexington
Luxurious Downtown Oasis Entertainment Features: Enjoy a game of billiards on the pool table during your stay at our property. Convenient Amenities: Benefit from free parking, fre…
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Quiet, gated oasis near downtown Lexington
620 North Limestone, Lexington
Quiet, gated oasis near downtown Lexington, a property where comfort meets convenience. Garden and Shared Lounge - Enjoy the tranquil surroundings and relax in the shared lounge a…
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Lexington Condo w/ Balcony: 1 Mi to UK Campus!
1411 Fontaine Rd, Lexington
Convenient Location This smoke-free apartment offers complimentary parking nearby. With a prime location just a 5-minute drive from Rupp Arena and Kroger Field, you'll have easy a…
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Lexington Vacation Rental 1 Mi to UK!
1411 Fontaine Rd, Lexington
Convenient Location This smoke-free apartment is conveniently situated near popular attractions such as Shriners Hospitals for Children and Ashland Henry Clay Estate. Enjoy easy a…
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175 LEX - Walkable Downtown Lexington & Rupp Arena - Full Condos
175 East Main Street, Lexington
Luxurious Renovated Property in the Heart of Downtown Lexington City Views and Modern Conveniences: Enjoy stunning city views and modern amenities including a fully equipped kitch…
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Hidden Gem
225 North Limestone, Lexington
Prime Location and Modern Comforts Located near Rupp Arena and Lexington Convention Center, Hidden Gem offers a cozy stay with a sun terrace and free WiFi. Enjoy city views from t…
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The Sire Hotel Lexington, Tapestry Collection by Hilton
120 West Second st, Lexington
Luxury Boutique Hotel in Lexington's Historic District Chic Rooms with Premium Amenities Indulge in luxury at The Sire Hotel Lexington with rooms featuring cable TV, en suite bath…
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Lyndon House B&B
507 N Broadway, Lexington
Victorian Charm and Modern Comforts Embrace the timeless elegance of our Victorian bed & breakfast in Lexington. Enjoy a complimentary cooked-to-order breakfast each morning befor…
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Chez Lyndon Manor
507 North Broadway, Lexington
Charming Victorian Bed and Breakfast in Lexington Individually Styled Rooms: Experience the elegance of 11-foot ceilings, vintage furniture, and floral bedding in each uniquely de…
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Residence Inn by Marriott Lexington City Center
150 W MAIN ST, Lexington
Luxurious Amenities Await at Residence Inn by Marriott Lexington City Center Modern Comforts: Indulge in a stay at our 3-star hotel featuring free WiFi, room service, and a fitnes…
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21c Museum Hotel Lexington
167 West Main Street, Lexington
Luxury and Culture Meet in Lexington Located just steps away from Hunt-Morgan House, 21c Museum Hotel Lexington offers a unique blend of luxury accommodation and cultural experien…
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Lexington Marriott City Center
121 WEST VINE STREET, Lexington
Luxurious Amenities and Services Lexington Marriott City Center offers a range of upscale amenities including free bikes, a seasonal outdoor swimming pool, and a fitness centre. G…
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Hilton Lexington Downtown
369 West Vine Street, Lexington
Luxurious Stay in the Heart of Lexington At the Hilton Lexington/Downtown, experience unparalleled convenience and comfort just steps away from the University of Kentucky and the …
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Hyatt Regency Lexington
401 W High St, Lexington
Prime Location in Downtown Lexington Connected to the Lexington Convention Center and Rupp Arena, Hyatt Regency Lexington offers convenience and comfort for both business and leis…
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WoodSpring Suites Lexington Southeast
2370 Lake Park Rd, Lexington
Convenient Location Located in Lexington, WoodSpring Suites Lexington Southeast offers easy access to popular attractions such as The Arboretum, Ashland The Henry Clay Estate, and…
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Luxurious 3 BR Distillery District Townhouse
955 Tarr Trace unit 2110, Lexington
Modern Amenities Experience luxury with a fully equipped kitchen, flat-screen TV, and free WiFi in this 3-bedroom townhouse. Convenient Location Located just steps away from Rupp …
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DoubleTree Suites by Hilton Lexington
2601 Richmond Rd, Lexington
Luxurious 2-Room Suites Indulge in spacious 2-room suites furnished with state-of-the-art amenities at the heart of Kentucky's horse country. Convenient Location Explore popular a…
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The Manchester Hotel
941 Manchester St, Lexington
Modern Accommodation with Premium Amenities Located in Lexington, The Manchester Hotel is a top choice for travelers seeking comfort and convenience. With free bikes, private park…
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Country Inn & Suites by Radisson, Lexington, KY
2297 Executive Dr, Lexington
Convenient Location and Amenities Located just 5 miles from downtown Lexington and the University of Kentucky, Country Inn and Suites Lexington offers a daily buffet breakfast. Th…
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Holiday Inn Express Hotel & Suites Lexington-Downtown University by IHG
1000 Export St, Lexington
Free High-Speed Internet Access and Indoor Pool Guests at the Holiday Inn Express Hotel & Suites Lexington-Downtown University can enjoy complimentary high-speed internet access i…
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Red Roof Inn & Suites Lexington - Hamburg
2241 Elkhorn Road, Lexington
Convenient Location Located just 8 km from the University of Kentucky and a short drive from the Kentucky Horse Park, Red Roof Inn & Suites Lexington - Hamburg offers a prime loca…
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Microtel Inn by Wyndham Lexington
2240 Buena Vista Rd, Lexington
Convenient Location and Amenities Located just 15 minutes east of downtown Lexington and the University of Kentucky, Microtel Inn by Wyndham offers free Wi-Fi, parking, and a cont…
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Holiday Inn Express & Suites Lexington Midtown - I-75 by IHG
2255 Buena Vista Rd, Lexington
Luxurious Amenities Holiday Inn Express & Suites Lexington boasts an indoor pool and a modern fitness centre, ensuring guests can relax and stay active during their stay. Each roo…
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Bluegrass Extended Stay
2753 Richmond Rd, Lexington
Convenient Location Located just a 10-minute drive from downtown Lexington and the University of Kentucky, Bluegrass Extended Stay offers easy access to the city's main attraction…
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SpringHill Suites by Marriott Lexington Near the University of Kentucky
863 South Broadway, Lexington
Luxurious Accommodations The SpringHill Suites Lexington offers spacious units with separate living areas and modern amenities such as flat-screen TVs and free Wi-Fi. Guests can e…
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Days Inn & Suites by Wyndham Lexington
1987 N Broadway, Lexington
Convenient Location and Modern Amenities Fitness Centre and Free Parking: Stay fit and park stress-free at our hotel with a fitness centre and complimentary private parking. 24-Ho…
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Red Roof Inn Lexington
1980 Haggard Ct, Lexington
Modern Accommodations with Convenient Amenities Located just 3 miles from central Lexington, the Red Roof Inn offers comfortable rooms equipped with a flat-screen TV, work desk, a…
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Guesthouse Inn & Suites Lexington
2261 Elkhorn Road, Lexington
Convenient Location and Modern Amenities Located just off Interstate 75, the Guesthouse Inn & Suites in Lexington offers a comfortable stay with free WiFi. Each room features a fl…
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Hampton Inn I-75 Lexington/Hamburg Area
2251 Elkhorn Rd, Lexington
Amenities and Features: Enjoy a relaxing stay at our hotel with an indoor pool and fitness center. Stay connected with complimentary wireless internet access and indulge in a dail…
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Fairfield Inn & Suites by Marriott Lexington East/I-75
2211 Elkhorn Road, Lexington
Convenient Location Located just a short distance from popular attractions like Rupp Arena and the Lexington Convention Center, Fairfield Inn & Suites by Marriott Lexington East/I…
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Best Western Lexington Inn
2221 Elkhorn Rd, Lexington
Indoor Pool and Complimentary Breakfast Stay refreshed with a dip in the indoor pool and start your day right with a complimentary on-the-go breakfast. Convenient Amenities Enjoy …
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Courtyard by Marriott Lexington North
775 Newtown Ct, Lexington
Indulge in Comfort and Convenience Modern Amenities Enjoy a relaxing stay with our indoor pool, free WiFi, and well-equipped guest rooms featuring flat-screen TVs, desks, and mini…
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Candlewood Suites Lexington by IHG
603 Adcolor Dr, Lexington
Spacious Suites with Full Kitchen Located just 3 miles from the University of Kentucky, Candlewood Suites Lexington offers spacious suites with free Wi-Fi and a full kitchen. Each…
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Comfort Inn & Suites Lexington - Hamburg I-75
2400 Buena Vista Rd, Lexington
Indulge in Relaxation Experience the ultimate comfort at Comfort Inn & Suites Lexington with an indoor pool and free WiFi. Each room is equipped with a microwave, refrigerator, wo…
Staying near a specific Winchester venue
This is usually the better question. The hotels above are measured from the middle of Winchester, which is only the right anchor if the city itself is the trip. If you are coming for one event, what matters is how far you are from that building at 11pm — and in most cities the centre and the venue are not the same place.
Each page below runs its own search from that venue’s own coordinates and sorts by real straight-line distance from the doors, with a plain note on every card saying whether that is a walk, a long walk or a drive.
Venues in Winchester
The buildings people book these rooms for. Each links to its schedule and tickets.
What is on in Winchester
The reason most people book a room here. Every date links to live tickets and a seat map.
How to read these listings
Every card carries the same facts in the same order, so two properties can be compared at a glance rather than read as marketing copy.
- Distance is straight-line, not walking. We know where the property is and where the centre is; we do not know the streets in between. That is why each card also says walkable, long walk or drive, and why those labels are deliberately conservative.
- Guest scores are our accommodation partner’s, not ours. StubOrder does not review hotels. Where a score appears it is theirs, with the review count beside it so you can judge how much weight it carries.
- The rate is the lowest available for the stay you asked for, for two adults, and it moves constantly. Treat it as a comparison between properties rather than a quote.
- Nothing here is paid placement. The order is distance from the centre, full stop. No property pays to appear or to rank.
Plan the rest of the trip
Frequently asked questions
How close are these hotels to the Winchester venues?
The hotels on this page are measured from the middle of Winchester. For distance from a specific building, use that venue's own page - each one is linked above and sorts every nearby property by real distance from the doors.
Does StubOrder sell hotels and tickets together?
No. Tickets come from our resale marketplace and rooms from our accommodation partner, as two separate bookings with separate confirmations.
Is it cheaper to stay near the venue or in the centre?
It depends on the city and the night. Near a stadium on an event night is usually the expensive option; the centre is usually better value but adds a journey. Both pages exist so you can compare them rather than guess.
What kind of hotels are there in Winchester?
The stock is mixed, with 3-star the largest single band at 58 of 117, and 3 of them are within a mile of the centre. They average 8.4/10 in guest scores from our accommodation partner.
Why are no prices shown until I pick dates?
Because a nightly rate only means anything for a specific stay, and asking for one costs a live request. Pick your dates and every property above is priced for exactly those nights, for two adults.
