𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Winchester (2026)

A historic downtown area with a prominent clock tower and a green-roofed building.

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Our top choices for Winchester hotels

A hotel lobby with a reception desk, a sofa, a chair, a desk with a telephone, and a computer.

A hotel entrance with a glass door, a reception area with a desk, chairs, and a plant.

A hotel room with a large bed, two bedside tables, a chair, a window with curtains, and a painting on the wall.

A hotel room with a sofa, a small table, a lamp, a mirror, a television, and a wardrobe.

1. Quality Inn Seaman

Seaman

Melissa

S$127

includes taxes & fees

22 Nov - 23 Nov

A hotel room with two beds, a desk, a TV, and a painting on the wall.

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

A motel with a red roof and multiple rooms, a parking lot, and a grassy area with trees.

A modern bathroom with a large mirror, a sink, a toilet, and a shower area.

2. Country Nights Inn

West Union

David

S$120

includes taxes & fees

26 Oct - 27 Oct

A brick building with a sign reading "French Quarter Inn" and a large dome structure in front.

A dining area with multiple tables and chairs, large windows, and chandeliers.

A view of a river with a bridge and a forested hillside in the background.

An outdoor seating area with tables and chairs, overlooking a river and a bridge.

3. French Quarter Inn

Maysville

Jessie

S$155

includes taxes & fees

1 Nov - 2 Nov

A bedroom with a bed, a dresser, a vanity with a mirror, and a door leading to another room.

A bathroom with a wooden vanity, a large mirror, and a red chair with a patterned cushion.

A bedroom with a wooden bed, a red chair, a small table with a lamp, and a ceiling fan.

A kitchen with a blue and white color scheme, a wooden chair, a table, a window with a view, and a microwave.

4. Moon River Bed and Breakfast

Maysville

Angela

S$170

includes taxes & fees

2 Nov - 3 Nov

A hotel room with a bed, bedside table, lamp, TV, and a desk with a chair.

A clean, well-lit cafe with wooden tables and chairs, a coffee machine, and a TV mounted on the wall.

A modern bathroom with a bathtub, a desk, a chair, and a flat-screen TV mounted on the wall.

A lobby with a light blue sofa, two matching armchairs, a wooden coffee table, and a framed map on the wall.

5. Countryside Inn & Suites

Mount Orab

Robert

S$117

includes taxes & fees

25 Nov - 26 Nov

A modern living room with a dark gray sofa, a wooden coffee table, and potted plants.

A breakfast area with a coffee machine, microwave, and various food dispensers.

A hotel room with a large bed, two wall-mounted paintings, a nightstand, a bedside lamp, and a chair.

6. Days Inn by Wyndham Hillsboro

Hillsboro

Jill

S$150

includes taxes & fees

27 Oct - 28 Oct

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

A blue Pepsi vending machine with various drink options.

A compact laundry room with a stainless steel refrigerator, a washing machine, and a dryer.

A corridor with doors numbered 209, a covered walkway, and a view of parked cars and greenery outside.

7. Paragon Inn Hillsboro

Hillsboro

Bonnie

S$105

includes taxes & fees

26 Oct - 27 Oct

A hotel room with two beds, a wooden headboard, a nightstand with a lamp, and two framed pictures on the wall.

A building with a blue roof and a large garage door.

Two front-loading washing machines in a laundry room with tiled flooring and a trash can.

8. Greystone Motel

Hillsboro

Gina

S$89

includes taxes & fees

26 Oct - 27 Oct

A hotel room with two beds, a nightstand, a painting, and a bathroom visible through an open door.

A motel entrance sign with a flower bed and a pumpkin.

A covered outdoor area with a wooden deck, benches, and a row of windows.

A covered outdoor area with a stone building in the background, a grassy lawn, and a gravel pathway.

9. Brown's Motel Aberdeen

Aberdeen

Kelly

S$78

includes taxes & fees

26 Oct - 27 Oct

A hotel room with two beds, a cityscape painting, and a mounted air conditioner.

A room with a flat-screen TV mounted on the wall, a window with a geometric patterned curtain, a desk with two chairs, and a door with a vent.

A two-story motel with a blue exterior, a front porch with potted plants, and a parking lot.

A compact kitchen with a sink, microwave, black refrigerator, stove, and wooden cabinets.

10. Hillsboro Inn & Suites

Hillsboro

Audrey

S$113

includes taxes & fees

26 Oct - 27 Oct

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

A hotel lobby with a reception desk, leather armchairs, a framed picture on the wall, and a tiled floor.

A hotel room with a sofa, a desk with a chair, a round mirror, a wooden ceiling railing, and a floor lamp.

A hotel reception area with a desk, computer, chair, and a reception counter.

11. Super 8 by Wyndham Maysville KY

Maysville

Tony

S$96

includes taxes & fees

3 Nov - 4 Nov

A wooden cabin interior with a sofa, a television, and a sliding barn door.

A wooden cabin kitchen with a sink, bar stools, a coffee machine, and a window with a view of trees.

12. Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

Rome

S$231

includes taxes & fees

30 Oct - 31 Oct

A hotel lobby with a chandelier, framed artwork, a reception desk, and a chair.

A hotel lobby with two armchairs, a coffee table, and a dining area in the background.

A hotel room with two beds, a nightstand, a lamp, and a chair.

An indoor swimming pool with clear blue water, surrounded by white lounge chairs and a sunlit room with a door leading to another area.

13. Quality Inn Maysville

Maysville

Stanley

S$108

includes taxes & fees

22 Nov - 23 Nov

A modern living room with a dark blue sofa, a patterned rug, and a green wall feature.

A spacious living area with a fireplace, a blue sofa, and a patterned rug.

A two-story building with a dark exterior and a red-tiled roof.

A bedroom with a large bed, floral curtains, a painting, two bedside lamps, and a nightstand.

14. The Benchmark Inn

Augusta

Oliver

S$399

includes taxes & fees

26 Oct - 27 Oct

A waiting area with a brown sofa, red chairs, a small table with a plant, and a bookshelf with magazines.

A kitchen area with a brick wall, framed pictures, a coffee machine, and a microwave.

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

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

15. Days Inn by Wyndham Maysville Kentucky

Maysville

Susan

S$112

includes taxes & fees

22 Nov - 23 Nov

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Learn more about Winchester

Check out Adams Lake State Park and Serpent Mound—just a couple of the sights around Winchester.

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Top Winchester Hotel Reviews

Hillsboro Inn & Suites

8/10 Good

"Clean. Very good access to nearby eateries. Bob Evan’s is 7 minutes away and fast food is closer. Liked parking at door by room assigned. Quiet place to sleep. Would have liked more sports options on tv."

Paragon Inn Hillsboro

10/10 Excellent

"The room was clean and the bed was very comfortable. It was in a good location and the price was very reasonable. I would definitely stay again if ever in the area. The only down fall was they didn't have a coffee pot."

Greystone Motel

10/10 Excellent

"Room was nice,quiet,and tidy. The workers were helpful and amazing. I just needed a night away to clear my head and that's exactly what I got."

The Benchmark Inn

10/10 Excellent

"Great stay very nice property"

Days Inn by Wyndham Maysville Kentucky

8/10 Good

"No safety lock on door. No stopper for tub. Toliet set was way loose and lid would not stay up. It’s a nice place to stay everything needs to be updated from time to time."

Moon River Bed and Breakfast

10/10 Excellent

"Quaint town. Lovely B&B. Very friendly staff."

Countryside Inn & Suites

10/10 Excellent

"Clean property and wonderful staff"

Quality Inn Maysville

8/10 Good

"The pool is permanently shut down. Also had to carry all belongings up multiple sets of stairs. Other than that, it was clean and comfortable. Front desk staff was great."