Pet-friendly vacation rentals in Winchester

Really nice place off a quiet street in Bolivar/Harper’s Ferry. Very clean and exactly as advertised. Hosts provided great instructions and it was easy to access and enter. Convenient to hiking trails and sight seeing. Would stay here again and recommend.

Had a great stay at the burrow with 5 friends and a doggy on our road trip. Cozy and clean, with a picturesque view from the porch. Our favorite part was the outdoor fire - thanks to the hosts for helping us get it going. Would definitely come back!!

Our family loved our stay at Ken's place. The house was extremely clean, the listing gave us a great feeling going into the rental, and we were not disappointed upon arrival. The property and scenery were fantastic. Our kids loved going out onto trails, creek, hot tub, local lake, and feeding the animals. We all wish we booked a longer stay and we will be back in the near future.

Really beautiful place with lots of character! So peaceful and amazing views!! We loved it. :). Thanks Julie!

I had a wonderful stay at 7 Elms. I had to come to the area for a work event in Gainesville, and my team and I decided to stay at this AirBNB. It was so lovely. Such a cool restoration of an old farmhouse, and the property was serene and wonderful. We didn't have time to explore the area, as we were working so much and long hours. the only thing I can speak to is the grocery store - and it had everything. We saw a bunch of wild animals during morning coffee time, and that was really special. I don't think I've actually ever seen groundhogs in person, and there's a hysterical duo that run the show. The hosts were easy to communicate with.

Very peaceful, a place to get away and relax. Restful. Grounds are well cared for.

Clean, well-stocked, spacious, and comfy! Town was a five minute walk with some great local shops and restaurants. Enjoyed our stay!

Traveling for my brothers wedding so just stayed for the night, but I enjoyed it very much!

Peaceful and perfect little getaway! Stephen’s cabin in the woods was quiet, cozy, and surrounded by nature.. Thanks for the awesome stay!”

Beautiful property, beautiful views, and an unbelievable night sky. It's definitely a place you want to try.

Lenah's place was wonderful! We were in Bealeton for a friend's wedding, and it was so close to everything we needed (including Moo Thru) but still in a rural setting. The house was spotless and had all of the amenities we could want. Lenah was even so sweet to loan me her iron so I could iron the dress I took for the wedding. We loved our stay and would definitely recommend it!

Excellent host. Very clean place, beautiful property. Laura was amazing. It was like staying with a good friend. We bought some of her eggs and delicious honey. We would definitely stay there again. My wife and I and our fur babies will miss Laura, Jerald, and Dasher.

If you read the reviews from others who stayed here...they were SPOT ON! Lynn's carriage house is like stepping into an immaculate barndominium. You feel like you are prepping for your fox hunt or what my wife and I did, enjoy a tea or glass of wine in the evenings watching the deer come through the fields or the horses in the far fields graze. PEACEFUL. The house has everything you need from coffee, tea, sweeteners, to spices and pots and pans. Come here to relax. Last, the pool on the listing is at the main house. Never did we feel like it wasn't our own private oasis. So cool to enjoy the pool surrounded by horse properties. Lynn is an excellent host. This is an incredible property.

We really enjoyed our stay here. The house offered so many things for us to do as a family. We had such a good time playing darts, pingpong, board games, and hanging out around the fire pit. The Woods is our favorite place to go because of all the amenities. Highly recommend!

We had a wonderful stay at Majestic Meadows. Sandy & Chris were wonderful hosts and the property was a great home away from home, with a beautiful courtyard full of colorful birds, a private pool, and a ton of flowering plants. Close enough to town to not feel like you’re in the middle of nowhere, but far away enough to feel secluded. I wouldn’t hesitate to book here again. Highly recommend.

Beautiful place in a beautiful area! They had everything we needed

A Hidden Gem of Art, Nature, and Peace Staying at Creekside Retreat at the Jewel Vinsotain in Smithsburg, MD was nothing short of magical. Designed by an artist, the suite has a private gallery—carefully curated, beautifully lit. The setting couldn’t be more idyllic: tucked beside a peaceful wooded area with a gentle creek flowing nearby, the sounds of water and birdsong was just what I needed to relax. Just steps from the property begins a sculpture trail that winds through the a wooded area. It’s rare to find a place that so seamlessly blends art, nature, and hospitality. This is more than a place to stay; it’s an experience that lingers long after you leave. Highly recommended for art lovers, nature seekers, and anyone in need of creative renewal.

This was a perfect stay for me and my dog! The cottage was so cozy and immaculate, exactly as described. Caylyn and Cody were very friendly and communication was excellent. We were so comfortable here and would easily stay again.

Absolutely loved this little getaway for my husbands birthday! It was so quiet and peaceful but had everything we needed. The design was so well thought out and absolutely beautiful. Reagan was amazing with recommendations and so quick to respond - I cannot wait to come back to the Treehouse! I wish I could have stayed longer.

Beautiful farm cabin, huge property to walk around, all amenities needed for a relaxing weekend, and probably the cleanest Airbnb I’ve ever walked into … Definitely recommend.

We loved this cozy cabin!! from the moment we arrived, everything exceeded our expectations. The house was spotless and stylishly decorated. it was thoughtfully stocked with everything we could possibly need. The layout was perfect for our family of four... spacious, comfortable and welcoming. The location was ideal, tucked away in a peaceful area but still close to everything we wanted to explore. We especially loved relaxing in the hot tub in the evenings and waking up to the serene surroundings each morning. every detail, from the fresh crisp linens to the plentiful amenities made it feel like a true home away from home. The hosts were fantastic! Matt was communicative, kind and clearly takes great pride and maintaining this property. We have stayed in many rentals and this one ranks as one of our favorites. If you're looking for the perfect blend of comfort, charm and convenience, this is the place. we're already talking about coming back!

We could not have nicer things to say about the hosts, the home, and the local community. Excellent restaurants in town with some nice markets, everything you need is close by. The hosts were extremely accommodating, provided excellent instructions/recommendations in their communications. The home was very well designed and equipped with everything needed for a relaxing stay.

This is an amazing home on a mountain side. You have a spectacular view of the mountains and the sunsets were incredible. The home is well furnished and tasteful. The beds very comfortable. It is a restful location and no need to go driving around. I would stay anytme.

Had a great weekend at the cabin. The location is off the grid and the surroundings are simply amazing. The cabin is neat and modern and super comfortable. Alex was responsive and the check in and check out were simple. If you need to get a way from it all but would still like some creature comforts, then this is the ideal location. 100 percent recommended.