Vacation rentals in Winchester

Melissa is the best host! She always makes me feel at home when we come to stay!

This was our second time staying here and we loved it again! Great place for a weekend getaway! Thanks!

Having lived in Pike County years ago and being familiar with Florence, staying in Ole Brick feels like coming home. It's both close enough and far enough away from everything and Nancy is a great host. I truly enjoyed my stay and hope to return.

Linda's house is Well stocked and Inviting. We enjoy staying here. The beds are comfortable and there is enough room for all my family. Thank You for another Lovely stay. See you in October! 🙂

We just spent our winter holiday at The Campground House. It was perfect for our multi-generational family. The weather was rainy so we didn't get to do much exploring but being together was more important. The house felt just like home. Thank you so much. The Wilson/Ono Family

It was decorated for the season and overlooked the town square which was also decorated for the season, and where there was a holiday celebration while we were there. Wonderful stay

We immediately felt very comfortable; everything was as described (actually, even better!) and we felt like we were staying at an old friends house. Super clean, with everything needed if you want to prepare your own meals. It was just the two of us, so we had plenty of room. I think it would also be perfect for a small family. We felt safe and the area was quiet and convenient. We spent most of our time in Springfield, which was an easy 30 min drive. We loved being able to come back to Petersburg to relax. Highly recommend this property; the owners were a joy to work with!!

Our weekend stay was absolutely incredible. The photos and descriptions online set the bar high, but the experience surpassed all our expectations. We loved kayaking on the private lake, strolling the scenic trail, and dining at charming local spots. Tammy was a fantastic host—warm, welcoming, and attentive. We’re already looking forward to coming back!

My family of 5 spent 4 days in Kyle and Emily’s residence, which was amazing. The home had all of the necessary amenities, which was greatly appreciated. I found it very hard to leave the home at times, because it was so relaxing, from the beds to the reclining couch. I would definitely recommend this house if you are visiting the area!