House holiday rentals in Winchester

This BnB is in contention for my FAVORITE stay of all time. Family of 6 adults and 1 child had more than enough space, and Jeanne really made our stay effortless. We felt right at home and we didn't have to make that last minute trip to the store you sometimes have to make bc the host skimped on providing toilet paper or dish soap, because she honestly thought of EVERYTHING ❤️ My granddaughter loved the pool and dips in the hot tub after swimsmade the adults happy. The location and view are to die for, and the two pups were ecstatic playing in the large fenced area. We spent a lot of time outside, plenty of furniture, fire pit, just eating dinner on the deck. (Missing NOTHING in the kitchen either!) Our last night we spent sitting and talking on the deck trying to identify the multitude of frog voices from the pond, before we parted ways to our various home states. I am most grateful for memories made and we are definitely considering a repeat! ❤️Thank you!

Place was beautiful and clean. The hosts responded right away when we had a question. If you’re thinking about staying here, this is your sign to book it!

This was such a wonderful home! As other reviewers said, lots of room for a big group to spread out. We had 8 guests. (6 adults and two kids) We explored Harpers Ferry and enjoyed hiking the Maryland Heights Trail. We felt absolutely comfortable hanging at this serene house for our mornings and evenings. Cooked most of our meals, played billiards, sang karaoke, and enjoyed the plunge pool. We had an epic round of hide and go seek. Great interior design and lots of space to spread out for quiet time, and many perfect reading nooks. Thanks Leigh, for being so responsive and friendly!

Our experience at the Wizards Escape was amazing! Nate, our host, was the best. He checked in to make sure that we were getting the best experience out of the house. The atmosphere is unreal! We really felt we were at Hogwarts Castle. The bedrooms are so full of detail. The kitchen is stocked with everything you could imagine. The Great Hall is magical! The escape rooms.. fantastic. We only stayed 2 days but tried to get in all the activities that were available. We played quidditch golf, did escape rooms, had a scavenger hunt, made great meals in the Weasley's kitchen. We had dinner in the Great Hall under the levitating candles while listening to the Harry Potter music in the background. This house is a home to be experienced. We are definitely coming back!

I needed a place that my family, from out of state, could stay while attending a graduation. The house was perfect! I told Bob what I wanted to do and he was encouraging and helpful. He made sure we had propane for grilling and answered all my questions. He was very prompt when I reached out to him. We had an amazing time. I would stay there again.

Thank you so much for the great stay! We enjoyed the area and were able to relax at your place.

My husband, brother, and two of our friends spent the weekend at Brad’s house and we had a lovely time. It was extremely conducive to relaxing. We cooked our meals there. The kitchen was very clean and we had found everything we needed for our meals. We were able to use lies the front porch. The pool was closed, but it looked very nice. Brad is an amazing host. He will answer your questions quickly. I would highly recommend staying at Brad’s place to anyone.

Duane and Matt were absolutely wonderful hosts! They helped make our quick weekend getaway truly unforgettable. Every amenity at the property was thoughtfully provided, and our daughters enjoyed every bit of it. Even while traveling internationally, Duane remained incredibly attentive and responsive, going above and beyond to ensure our stay was perfect. One of the highlights for our girls was getting to meet a baby sheep—such a thoughtful and special touch! They were especially taken with little Pinky Pie and are still talking about her. Thank you again, Duane, for sharing your beautiful property and creating such a memorable experience for our family!

Tyler & Erica, thank you for the use of your beautiful home. We enjoyed the peaceful setting by the river. God bless. Josh & Lori

We really enjoyed our stay in this house and Suranny was very responsive and helpful. The house was clean as can be and very spacious. Lots of natural sunlight and a wonderful covered porch to sit out on. The beds were very comfortable and the bathrooms were clean. We would certainly stay here again in the future.

We thoroughly enjoyed our extended stay in this charming cottage! The location is ideal for walking—- either around the neighborhood or downtown. We loved the charm and cozy atmosphere and spent a lot of time on the sun porch too! Can’t recommend it highly enough and look forward to staying here again

This is the second time staying in this beautiful home. Marie has everything you need for a perfect stay. The area is so beautiful and the home is soooo cozy. We will definitely be back.

Great location next to old town! Lots to do if you want to go out for a walk and many places to dine in. Felt like home and enjoyed the backyard area. Highly recommend!

The home suited us very well. It was described just like it sits. The hot tub was so relaxing in the late afternoon as well.

Best Airbnb experience, the place was spotless, well stocked and had incredible views. Easy drive from DC, great hiking in the National park nearby. The hot tub was fantastic, secluded so you relax. I didn’t use the barn space but it looked amazing. I loved the fire pit. I can’t remember seeing many sunsets without houses or buildings in the view… here you can. This is the one airbnb I would want to come back to consistently. Great hosts, perfect for a getaway to West Virginia for some peace and quiet. Next time I’ll stay longer now that I know what to expect.

This is the 2nd time I’ve stayed at this airbnb and it never fails to amaze me! This was my boyfriend’s first time experiencing the breath taking views this place has to offer and it did not disappoint! We went for a little walk around the neighborhood during our stay - it was peaceful and beautiful. The home itself has everything you need for a comfortable stay and unbeatable surroundings. The host was responsive and kind. I hope we can come back in the future!

Kara is a wonderful host and it is clear she takes great pride in her property. The home itself is very nice and comfortable. As other reviews suggest, the house sits very close to 522 and gets a lot of road noise. There were more breaks in this on the weekends but very busy during the week especially during morning and early evening hours. The stream in the backyard is really cool and helps dampen the road noise as well. The house is very convenient to Cacapon State Park which is beautiful, peaceful and full of great hiking trails. As long as you don’t mind road noise where you are staying, this is a great place!

The place was perfect for our family. Stacey was fantastic and very responsive. Definitely recommend this Airbnb.

My family and I had a lovely weekend stay at Dominic's. Beautiful home tucked away from the main road. Very modern with high quality amenities and details all of which were really appreciated - from comfortable beds to kitchenware to even the soap and shampoo in the shower. It felt like no expense was spared. Note that one of the single beds is a trundle bed (not pictured), though the accommodations were just enough for the six of us. On a clear night, we could see the stars very clearly from both front and back yards. I think the pictures don't do the place justice - this was a wonderful stay. Thank you!

Jamie and family are the best. It was one of the best moments of our lives and it was a great experience. I’d recommend it 100%. They are such a great hosts and we felt right at home. We appreciate them so much and we are so thankful for all. Please come and visit this great place and family.

Hart's Overlook was everything we wanted and more! My husband and I came here and stayed a week for our honeymoon. The pictures don't do the views justice. It is beautiful, quiet and peaceful. The tiny house was immaculate. If you want to go somewhere where there are things to do, this is not the place, but if you want what we wanted - to get away for some serious relaxation and peace - then this is for you! I already want to go back. We definitely will be staying there again.

My girlfriends and I stayed here for a weekend girls trip and unanimously agreed—this was the best Airbnb we’ve ever stayed in. The space was spotless, beautifully decorated, and incredibly well-stocked. From the cozy blankets to the ample seating and thoughtful touches throughout, everything felt intentional and welcoming. The amenities were top tier and made our stay feel elevated yet comfortable. Tracy was a fantastic host—super responsive and helpful. She reached out with helpful info before we even had questions, which made everything smooth and stress-free. Highly recommend this stay to anyone looking for a relaxing, well-appointed getaway!

What a wonderful mountainside retreat! The home is beautifully decorated and spotless. All the unique touches gave the place a loving feel. It is a peaceful setting and the view is spectacular. April was thoughtful in her suggestions of places to eat and things to do in the area. She responded quickly to any messages sent. She is a great host. My husband and I hope to return soon!

Jeanne was an outstanding host! Easy to communicate with quick responses to any questions. The house was amazing and truly exceeded our expectations. It was spotless! The cleanest rental I have ever stayed in. The grounds were so serene I didn’t want to leave. Thank you for making our weekend getaway such a success!