Guesthouse holiday rentals in Jefferson County

Peyton was such a fantastic host! She was accessible, responsive, and committed to providing an excellent experience. I emphatically recommend staying here!

Lisa and Scott are warm, kind and wonderful hosts. Loved the stay and the home-made breakfast. A hiker's paradise!

This is a beautiful, private place with amazing nature. We saw deer and hummingbirds, and they were pretty close to us. This place has a wonderful cat (Mr. Moo) who will give you much love! It is a bummer that we didn’t see dogs, but we got to see the chickens and got eggs from them! Amazing place! Although we may not hear beautiful sounds like others mentioned, we felt the peace and mindless presence. We enjoyed our time, and it was a perfect place for our short retreat.

I had a great stay at the charming little house. It was located right on the street, but the noise was not a problem because it was just about a block from town. I would stay there again in a minute!

This place was our best choice even before we realized there would be a freshly-prepared, multi-course gourmet breakfast. House is as advertised, clean, and well-located. Scott and Lisa are friendly, responsive, and fantastic cooks. Enjoy!

My family had an idyllic time here. Perfect home base for hiking and swimming at the state parks in the area. Good to know for families since it’s hard to tell in photos: - This is essentially a studio apartment, meaning there aren’t full walls that separate the bedroom from the living space so bring a white noise machine - there is wonderful natural light in the apartment but some are sky lights that will be impossible to cover for naptime. That being said, we had a wonderful time with our 4mo old and 4 year old. They have hummingbirds and birds of all colors and lots of instruments, games, and art to experiment with. If your kids are between crawling age to 3 yrs old, all the things in the apartment may stress you out, but it was perfect for a curious 4 year old. We walked the art hike in the backyard at least once a day, which our dog loved, and Sarah even set us up with their firepit to make s’mores. Magical! Truly a trip to remember! We hope to visit again!

We had an amazing stay here, especially considering we got snowed in on Saturday and still had a great time! The area is beautiful, the neighborhood trail was fun to explore, and the history of Berkley Springs is fascinating. Jeff was kind and friendly, offered great recommendations, and very responsive to questions. The house was very clean and we were able to make use of the kitchen and pizza oven. Perfect little getaway spot!

City dog farm was a beautiful farm conveniently located close to everything. Karen and her husband were the absolute best hosts. The place was very clean, spacious, and comfortable. Beautiful surroundings of nature, a donkey and horses near by, along with quiet and tranquility so you can relax while you get away. Will definitely stay here again.

Everything was top notch, pictures don't do the location justice. The ambiance is peaceful quiet fresh air beautiful views, the house is as listed and more, You get what you paid for. Leena is an amazing person very responsive and very hospitable. Don't think twice just book you will not be disappointed.

My girlfriend, our dog, and I stayed for over 30 days at this peaceful spot on Paxon Road in Round Hill, and it was exactly what we were looking for. The property is quiet, secluded, and surrounded by nature Wildlife wandered nearby and was totally unbothered by us or our dog. We loved being so close to a bunch of great wineries and breweries, too. The host was very responsive and made the whole stay easy. Highly recommend for anyone looking for a calm, nature-filled getaway.

Lovely place to stay. Loved seeing the donkeys!

My husband and I had a quiet weekend in The Plains and absolutely loved staying at Elizabeth's cottage! The cottage has exquisite furniture, cozy bedding and all the right touches to feel at home. I loved sipping coffee and watching the horses grazing in the pasture. Elizabeth and her family were so friendly and welcoming. We enjoyed walking to town for dinner and shopping. I can't wait to return to explore more of the area.

Convenient location to downtown Middleburg and a very comfortable place to stay. We were in town for a wedding at The Goodstone Inn and enjoyed the close proximity to the venue and to town. Tim's went above and beyond with a special welcome amenity as well as providing us with an iron upon request. Tim was very responsive and helpful during our stay and we would not hesitate to stay again when visiting the area. Thank you Tim for a wonderful weekend.

A perfect, peaceful retreat. We so enjoyed the huge jacuzzi tub and funky cool bathroom. We read books from the library and played board games on the screened in porch. The craftsmanship in the home itself is truly remarkable. Sleeping in a full bed was nearly impossible for us but luckily there’s a futon as well. Would come back. Clean, cozy, homey and lovely.

Great place for a quick visit to the area for a friends wedding. Lots of things to do in the surrounding area. Needed to stay longer to take it all in.

Loved our stay! We were here from DC mainly to hike and relax and the space was perfect for both! Location is close to the north entrance of Shenandoah National Park which was wonderful. We cooked most meals in the unit and it was well equipped for basic meals. Beds were comfy, AC/heaters worked great, and the views were spectacular. Host was lovely and quick to respond. Would definitely stay again!

We really enjoyed our stay at Melinda's and would stay there again in a second. The property is situated in the heart of God's country and is absolutely beautiful. The guest house is very comfortable and very quiet. Finding it was a little tricky. For some reason the app link for directions takes you close but not to the actual location. We eventually found the address, which is different from the address in the link, in a note from the host. We had not paid attention to that at a glance but it was clearly communicated in the note. We ended up eating dinner at a place called Anthony's Italian and Mediterranean restaurant and it was really quite good.

This was our first time to the area. My best friend was getting married at Bluemont Winery. Everything was as expected at the guest house. We loved our stay. We got to meet Bob and chat some. We did some hiking close by and saw the beautiful overlook. We had a tour all day Saturday of the wineries with a large group from the wedding. Brunch on Sunday at The Local. We even met Zena, one of the dogs, who was very friendly. We would definetly stay again. Thank you Nancy and Bob

This was my second stay at The Nest on Nixon Road, and once again, it was absolutely perfect. Returning felt incredibly comfortable and familiar—everything was just as clean, peaceful, and thoughtfully arranged as the first time. Traveling with my dog can sometimes be a challenge, but Emily makes it so easy and welcoming. The space is not only pet-friendly, but genuinely pet loved—my pup settled in right away. Having a quiet, cozy spot where we both felt comfortable, which made the whole trip stress-free. Emily is a fantastic host—kind, responsive, and clearly dedicated to making her guests feel at home. I’m so grateful to have found such a reliable and relaxing place to return to, and I’ll definitely be back again. Highly recommend to solo travelers (especially with dogs!) looking for a peaceful getaway.

Great place to stay for a peaceful weekend. Everything was clean and the space itself was comfortable and very quiet. We loved the firepit! Would highly recommend Anwar’s place.

We absolutely loved our stay here! It was super clean and very spacious! Amanda was a very accommodating host and I would definitely recommend this place!

JoAnne's place was truly lovely. She took great care to make us feel at home and added in little touches, like welcome snacks and bathrobes, to make us feel welcome. She truly cared about our comfort. The home is adorable and extremely comfortable in a beautiful, serene wooded setting. It's access to the W&OD trail cannot be beat! My mother absolutely loved her daily visits with Meister the Cat and we enjoyed sipping coffee on the front porch while soaking in the sounds of nature. Thank you, JoAnne!

This was our third stay. It's convenient to our family. Rooms are spacious and comfortably furnished. We have always had weekend stay, but this accommodation would be comfortable for a long stay. The kitchen has everything you need for cooking with a full size range and fridge. Jen provides easy instructions for coming and going.

We loved staying at Dustin’s place! It was the perfect place for a weekend getaway. It was in a great location for beautiful views but also things to do (breweries nearby and a concert in town on Saturday). Dustin was incredibly responsive and wanted to ensure we had a great time. Would definitely recommend this place to others!!