Places to stay in Winchester

I recently stayed at this cabin for the weekend, and it was a wonderful experience from start to finish. The cabin was exceptionally clean and well-maintained, making it feel immediately welcoming and comfortable. The surrounding area was incredibly peaceful — perfect for relaxing and disconnecting from the hustle and bustle of daily life. The setting was beautiful, with nature right outside the door, and it was clear that a lot of care was put into making the space cozy and inviting. The amenities were exactly as described (and even better than expected), and everything we needed was readily available. Overall, this cabin offered the perfect blend of comfort, tranquility, and charm. I would absolutely recommend it to anyone looking for a quiet getaway, and I’m already looking forward to coming back!

3rd time we have stayed here. It is a very beautiful and peaceful place. The mornings and evenings on the deck with coffee or a drink are amazing. Alona makes this place what it is. She is very attentive and helpful, always ready to help you make your stay a memorable one.

Our stay at Climb on Inn was great. The home is cozy, well equipped (the kitchen was great for cooking for our large group and is well stocked with generic non perishables, board games were fantastic, plenty of bedding, extra toiletries, etc) and private. The location was nicely central to the crags we climbed at. Deena was very welcoming, quick to respond, (even getting a coffee maker to us same-day when we found something was plugging the intake on the last one) and clearly cares about people having a good experience at her place. We will definitely be back to climb on in next time we visit RRG!

My family had a great stay in Eric's place. We would rent here again!

Highly recommend! Amanda’s house is BEAUTIFUL and very CLEAN! Our family of four stayed for a week and we loved our stay. House was spotless and comfortable. The location is great. You can walk to downtown Georgetown, which is great a downtown! We did day trips everyday and her house was a great location for this. Amanda also checked in on us to make sure everything was ok and gave us great recommendations. Great stay!!!

Loved my quick getaway to Lexington at the bourbon house. Super cute, clean and I took advantage of the bikes! Would stay again!

We only stayed for one night in Lexington, but the place was ready and clean at check-in time. Danny is a very responsive host. We were able to walk to nearby West 6th Brewing and Smithtown Seafood. Later had dinner in Lexington.

This was the most beautiful and ornate airbnb I've ever experienced! Everything's so charming and full of stories as this place is a true extension of Mr. Lee who is so full of love and life and you can tell he's eager to extend that to his guests. The only possible downside is theres no elevator so for quests who are handicapped and have a hard time with stairs this may not be for you considering there's a few flights to the room BUT Mr. Lee insisted to carry our bags and made sure we were comfortable. The decor is so unique and vibrant yet calm and the town of Paris is very quaint. We enjoyed our $25 gift card to Lee's restaurant and had the place to ourselves to dine. The room also had free organic bananas, muffins and drinks in the fridge. The whirlpool jacuzzi tub was also a plus! 10/10 would stay again.

Was in town for a college visit. This was the perfect home base to explore the college as well as the city of Berea. Hope it will be available for future visits as my daughter gets settled into campus life at Berea College.