Downtown Winchester, Kentucky

Discover shopping, dining, and accommodation in downtown Winchester.

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Hotels

Best Western Country Squire

1307 W Lexington Ave

Winchester, Kentucky

Holiday Inn Express Winchester

5250 Revilo Rd

Winchester, Kentucky

Quality Inn & Suites Winchester

960 Interstate Dr

Winchester, Kentucky

Hampton Inn Winchester

1025 Early Dr

Winchester, Kentucky

Red Roof Inn Winchester, KY

1100 Interstate Drive

Winchester, Kentucky

Hotel Tips

Always announce during booking if the trip is for a special event, anniversary or reunion. Group rates can be pre-negotiated and you may qualify for a lower cost and better upgrades for your stay. If you are the one setting up the event, always work directly with the front desk manager to make sure the best service is offered to your party.

Policies vary on the availability of pet friendly rooms to it is wise to be open, honest and upfront during the booking process. You may find yourself kicked out or even paying a large deposit if you are not in a pet-friendly hotel and bring one anyway. New ADA laws are fuzzy though as service animals are not required to be documented and proprietors are legally not allowed to ask if the animal is a pet vs. a service animal.

Always tip staff when you feel the service was great and don't forget the housekeeping staff which you may never see. You should tip every day if you are staying multiple days as the staff may rotate out and miss the bounty at the end.

Things To Do

Winchester is the place to plan your wedding. You'll be spending a lot of time downtown as there are so many wonderful shops to find invitations, photographers, bakers, caterers and jewelers. Planning your wedding will be a breeze with so much support from local merchants to make a perfect and memorable day.

Winchester has that special dining venue and you are sure to find something to please with numerous meals served to satisfy each palette. A wide variety of restaurants and delis are available to choose from with a nice selection of entrees and especially desserts.

Winchester gives several options to find the right piece of art as it takes time and a diligent effort to get just the right piece. Shopping for art downtown is the best way to locate your next purchase.

Why Do You Love Downtown?

Kathy Burchett

I've never been and I would like to visit the downtown area, during my visit. During our last visit, we were not aware of a downtown area. Thank You!!!

Rebekah Nelson

I'm visiting for the first time next week and I'm considering relocating to Ashland. I've heard so many great things about it!

Dianna Branden

I love the quaint little boutiques.

kristin Cutler

It's so cute and quaint.

Mary Loar

There are so many cute stores in Silverton. We are going on Thursday to shop and dine.

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