An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.

Cheap Hotels in Winchester

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Cheap Hotels in Winchester

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Winchester on Hotels.com. These Winchester Cheap Hotels consistently deliver on quality, location and traveler experience. Last updated on October 12, 2026.

An indoor swimming pool with a wooden ceiling, tiled walls, and a seating area with chairs and a table.

A lobby with a sofa, armchairs, a fireplace, a TV, and a patterned rug.

A modern hotel room with a bed, a desk, a chair, a sofa, and a large mirror.

A multi-story hotel with a prominent 'LaQuinta' sign, a covered entrance, and a parking lot.

1. La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

Lexington

CNY584

CNY677 total

includes taxes & fees

Oct 18 - Oct 19

A large indoor swimming pool with a tiled floor, surrounded by large windows and a seating area with tables and chairs.

A multi-story hotel with a curved entrance canopy, large windows, and a modern design.

A modern dining area with a central white table surrounded by blue chairs, a flat-screen TV mounted on the wall, and large windows offering a view of the outside.

A modern hotel lobby with a long communal table, blue and orange seating, a coffee station, and a large wooden door.

2. Holiday Inn Express Lexington - Horse Park Area by IHG

Lexington

CNY622

CNY722 total

includes taxes & fees

Nov 9 - Nov 10

A hotel lobby with blue walls, a seating area with blue chairs, a bar, and artwork on the walls.

An indoor swimming pool with a lifeguard station, poolside chairs, and a clear 3 FT depth marking.

A hotel room with two beds, a bathroom, and a hallway.

A guesthouse with a covered entrance, a large building with a tower, and a sign indicating an indoor pool.

3. GuestHouse Lexington

Lexington

CNY449

CNY522 total

includes taxes & fees

Oct 13 - Oct 14

A modern reception area with a wooden ceiling, a reception desk, seating arrangements, and a mural of horses.

A hotel with a covered entrance, a bell tower, and a parking lot.

A vending machine stocked with various beverages and snacks, including sodas and chips.

A hotel room with two beds, a desk, a chair, and a TV.

4. Clarion Pointe Richmond North near University

Richmond

CNY480

CNY529 total

includes taxes & fees

Nov 10 - Nov 11

A spacious lobby with a large seating area, a coffee bar, and a view of the kitchen area.

A buffet setup with clear glass serving stations and a coffee machine in the background.

A hotel room with a bed, a desk, a television, a chair, a sofa, and a window with curtains.

A banquet hall with round tables set for a formal event, featuring floral centerpieces and candles.

5. Quality Inn Lexington -Horse Park

Lexington

CNY382

CNY444 total

includes taxes & fees

Nov 8 - Nov 9

A hotel room with a bed, a desk, a chair, a television, and a bathroom.

A hotel reception area with a wooden reception desk, a red wall with a 'Free Wi-Fi All Rooms' sign, a stone wall with a 'Red Roof Inn' sign, and a black and red doormat.

A hotel room with a desk, chair, coat rack, wall-mounted TV, and a red chair.

A compact kitchenette with a microwave, refrigerator, and a small dining area with a table and chair.

6. Red Roof Inn Richmond, KY

Richmond

CNY358

CNY395 total

includes taxes & fees

Oct 18 - Oct 19

A reception area with a stone wall, a Baymont Inn & Suites sign, a refrigerator stocked with beverages, and a wooden counter.

A Baymont Inn & Suites building with a prominent sign, a covered entrance, and a parking lot.

A restaurant with wooden tables and chairs, a counter with a coffee machine, and a television mounted on the wall.

A large indoor swimming pool with clear blue water, surrounded by lounge chairs and a sunbed.

7. Baymont by Wyndham Georgetown/Lexington North

Georgetown

CNY461

CNY508 total

includes taxes & fees

Nov 2 - Nov 3

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Top landmarks in Winchester

Bluegrass Heritage Museum

7.4/10 (13 reviews)

The center of Winchester is home to cultural attractions like Bluegrass Heritage Museum, so you might want to stop by during your stay. If you want to experience more of the culture Winchester has to offer, head to College Park and Cassell Creek Golf Course.

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Cassell Creek Golf Course

7.6/10 (4 reviews)

You might want to practice your swing at Cassell Creek Golf Course, a golf course located 4.1 mi (6.6 km) from central Winchester. If Cassell Creek Golf Course doesn't quite scratch your golfing itch, Southwind Golf Course is also nearby.

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Southwind Golf Course

6.0/10 (2 reviews)

You might want to practice your swing at Southwind Golf Course, a golf course located 2.2 mi (3.5 km) from central Winchester. If Southwind Golf Course doesn't quite scratch your golfing itch, Cassell Creek Golf Course is also nearby.

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College Park

If you like spending time outside, why not spend the afternoon at College Park, a park located 17.3 mi (27.9 km) from the center of Lexington. Want to stretch your legs some more? Head to GRCHS Baseball Field, just a short walk away.

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Wiseman Park

If you like spending time outside, why not spend the afternoon at Wiseman Park, a park located 16.8 mi (27 km) from the center of Lexington. Want to stretch your legs some more? Head to GRCHS Baseball Field and College Park, both nearby.

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Winchester Opera House

If you're planning a bit of sightseeing during your trip, head to Winchester Opera House— just one of the monuments in central Winchester.

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Clark County Public Library

Clark County Public Library is worth a visit, located 0.5 mi (0.8 km) from central Winchester.

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The Holler

If you like spending time outside, why not spend the afternoon at The Holler, a park located 18.2 mi (29.2 km) from the center of Lexington. Want to stretch your legs some more? Head to Community Park and Lykins Park, both nearby.

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