2 Star Hotels in Winchester

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

2 Star Hotels in Winchester

A hotel room with a large bed, a desk with a chair, a window with a view of the outside, and a wall-mounted TV.

A modern kitchen area with a coffee machine, a fruit display, and a 'GOOD MORNING' sign on the wall.

A Holiday Inn Express building with a modern design, featuring a large entrance and a well-lit facade.

A coffee station with two coffee machines and a variety of coffee pods and cups.

1. Holiday Inn Express Lexington East - Winchester by IHG

Winchester

$98

$108 total

includes taxes & fees

Nov 16 - Nov 17

A restaurant with a counter, tables, chairs, and a kitchen area with appliances and food items.

A lobby with two armchairs, a reception desk, and a chandelier.

A hotel with a modern design, featuring a large building with multiple balconies and a well-maintained lawn.

A hotel room with a sofa, a desk, a chair, a lamp, and two abstract paintings on the walls.

2. Best Western Winchester Hotel

Winchester

$100

$110 total

includes taxes & fees

Oct 25 - Oct 26

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

A hotel breakfast area with a checkered floor, wooden cabinets, a microwave, and various breakfast items.

A reception desk with a 'Manager On Duty' sign, framed pictures on the wall, and a 'Welcome to Winchester' sign.

A store interior with shelves stocked with snacks and treats, a chalkboard sign reading 'Local Flavor,' and a 'Treats' sign on the wall.

3. Hampton Inn Winchester

Winchester

$110

$121 total

includes taxes & fees

Nov 8 - Nov 9

A swimming pool with wooden walls and large windows offering views of greenery.

A hotel room with two beds, a sofa, a desk, and a window with blinds.

A modern lobby with a sofa, armchair, and a coffee table. A flat-screen TV is mounted on the wall, and there is a window with a view of a tree and building.

A Baymont Inn & Suites reception area with a blue accent wall, a large window with a view of a pool, and a modern reception desk.

4. Baymont by Wyndham Winchester

Winchester

$76

$83 total

includes taxes & fees

Nov 16 - Nov 17

A hotel room with a bed, a desk, a chair, a desk lamp, a window with curtains, an air conditioner, and a view of the outside.

A ValueStay hotel entrance with a clear sign, a covered walkway, and a parking lot.

A lobby with a patterned carpet, seating area with chairs and a sofa, a small table, and a reception desk.

5. Value Stay

Winchester

$59

$65 total

includes taxes & fees

Nov 11 - Nov 12

An indoor swimming pool with tiled flooring, orange walls, and potted plants.

A waiting area with blue sofas and a brown ottoman, a reception desk, and a door leading to a hallway.

A hotel room with a large bed, a bedside table with a lamp, and a telephone.

A spacious dining area with multiple tables and chairs, a kitchenette in the background, and large windows allowing natural light.

6. Comfort Inn Winchester

Winchester

$69

$77 total

includes taxes & fees

Nov 16 - Nov 17

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 spacious lobby with a high ceiling, large windows, and a blue accent wall. There are multiple seating areas with chairs and tables, and a television mounted on the wall.

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

7. GuestHouse Lexington

Lexington

$64

$74 total

includes taxes & fees

Oct 20 - Oct 21

A hotel bathroom with a sink, mirror, towel rack, and a visible toilet.

A desktop computer setup with a monitor, keyboard, and Canon printer on a black desk against a beige wall.

A hotel with a lobby, a parking lot, and a building with a brown roof.

8. Days Inn Lexington SE/Hamburg

Lexington

$60

$70 total

includes taxes & fees

Oct 21 - Oct 22

A Holiday Inn Express & Suites building with a modern design, featuring a covered entrance and stone pillars.

A modern breakfast area with a yogurt dispenser, cereal, eggs, and milk station.

A hotel reception area with two reception desks, a wall-mounted sign for Holiday Inn Express Suites, and a Coca-Cola refrigerator stocked with beverages.

A hotel room with a bed, a microwave, a coffee maker, and a window with a view.

9. Holiday Inn Express & Suites Mt Sterling North by IHG

Mount Sterling

$111

$122 total

includes taxes & fees

Nov 18 - Nov 19

An indoor swimming pool with clear water, a pool ladder, and lounge chairs.

A hotel room with a bed, a desk with a chair, a sofa, and a TV.

A Comfort Inn & Suites building with a yellow facade, brick accents, and a clear blue sky.

A hotel lobby with a blue sofa, armchairs, a coffee table, and a reception desk.

10. Comfort Inn & Suites Mount Sterling

Mount Sterling

$82

$90 total

includes taxes & fees

Nov 16 - Nov 17

An indoor swimming pool with clear glass walls, lounge chairs, and a ceiling with recessed lighting.

A reception desk with a "Welcome to the Blue Grass State" sign, a wooden reception desk, and a "Hilton Honors" sign.

A modern hotel room with a flat-screen TV mounted on a wooden wall, a built-in microwave, and a coffee machine in a cabinet.

A hotel dining area with tables and chairs, a television, and a kitchen in the background.

11. Hampton Inn I-75 Lexington/Hamburg Area

Lexington

$88

$103 total

includes taxes & fees

Nov 16 - Nov 17

A spacious living room with a blue sofa, a grey armchair, and a fireplace.

A reception desk with a wooden finish, a glass partition, and a digital phone system.

A hotel room with two beds, a desk, a chair, and a large window with curtains.

A fitness center with treadmills, a mirrored wall, a clock, and a phone on a shelf.

12. Comfort Inn Lexington I-75

Lexington

$72

$84 total

includes taxes & fees

Nov 17 - Nov 18

A modern food court with a variety of food stalls, a coffee station, and a seating area with a view of the outside.

A modern lounge area with seating, tables, and decorative lighting.

An outdoor seating area with two sofas, a round table, and a planter with flowers.

A modern hotel building with a blue and grey facade, multiple windows, and a prominent 'tru by Hilton' sign.

13. Tru By Hilton Lexington Hamburg

Liberty Area

$81

$94 total

includes taxes & fees

Nov 8 - Nov 9

A lobby with two armchairs, a fireplace, and a large mirror.

A breakfast buffet with various food items and a pitcher of milk.

A hotel room with a bed, a bathroom, and a large mirror.

A gym with treadmills, a weight machine, and mirrors on the walls.

14. Ramada Limited Mount Sterling

Mount Sterling

$61

$67 total

includes taxes & fees

Nov 1 - Nov 2

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

A modern living room with a blue sofa, a small table, a desk, and a chair.

A hotel hallway with patterned carpet, doors, and a fire alarm on the wall.

A multi-story motel with a blue and white exterior, a paved walkway, and a well-maintained lawn.

15. Baymont By Wyndham Lexington

Lexington

$64

$74 total

includes taxes & fees

Oct 19 - Oct 20

A modern hotel lobby with a curved glass railing, a view of the outdoors, and a green carpeted floor.

A large indoor swimming pool with clear lanes, a lifeguard chair, and a view of the outdoors through large windows.

A modern hotel entrance with a covered walkway, large windows, and landscaped garden areas.

A modern cafeteria with green chairs and tables, a counter with food items, and a TV mounted on the wall.

16. Spark by Hilton Lexington Hamburg

Lexington

$76

$88 total

includes taxes & fees

Oct 25 - Oct 26

A restaurant with multiple tables and chairs, large windows, and a flat-screen TV mounted on the wall.

A breakfast bar with bread, coffee machines, and a sign for continental breakfast.

A Comfort Inn and EconoLodge with a gas station, parking lot, and a building with a green roof.

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

17. Econo Lodge Lexington Southeast

Lexington

$53

$61 total

includes taxes & fees

Nov 16 - Nov 17

A hotel room with two beds, a desk, a lamp, a painting, and a window with curtains.

A hotel lobby with beige sofas, a flat-screen TV, a reception desk, and a framed picture on the wall.

A motel with a 'Super 8' sign, a covered entrance, and a clear driveway.

A historical site with rustic wooden buildings and a person in period attire walking on a gravel path.

18. Super 8 by Wyndham Richmond

Richmond

$52

$57 total

includes taxes & fees

Nov 1 - Nov 2

A buffet with labeled containers of turkey sausage and cookies.

A parking area with electric vehicle charging stations, a building labeled 'Social Security Administration,' and a 'Shred-it' delivery truck.

19. Holiday Inn Express & Suites Lexington Midtown - I-75 by IHG

Lexington

$99

$115 total

includes taxes & fees

Nov 16 - Nov 17

A spacious living area with a modern staircase, a sofa set, and a dining area.

A hotel room with a brown leather sofa, two armchairs, a small side table, a lamp, and framed pictures on the wall.

A hotel dining area with wooden tables and chairs, a buffet counter with various food items, and a wall with framed certificates.

A hotel lobby with a wooden reception desk, a staircase, and a wall with a floral pattern.

20. Sleep Inn Lexington Hamburg

Liberty Area

$67

$77 total

includes taxes & fees

Nov 16 - Nov 17

See more properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

GRCHS Baseball Field

If you like spending time outside, why not spend the afternoon at GRCHS Baseball Field, a park located 17.3 mi (27.8 km) from the center of Lexington. Want to stretch your legs some more? Head to College Park, just a short walk away.

See properties

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.

See properties

Keep exploring

More ways to book

Book 2 Star Hotels in Winchester on Hotels.com