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28 Saf. - 2 Rab. I

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21 Rab. I - 23 Rab. I

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Compare 522 Vacation Homes in Winchester with updated reviews, rates, and availability.

"The location was exactly what we needed and wanted. If you want to totally relax, get semi off the grid, this is your place. Take a hike and take it all in. Thank you to our hosts for making such a great property available."

"We had a full family 4 day retreat and Jill’s place was perfect. Lots of room, beds were so comfy and contained all the kitchen and bathroom supplies we needed. Everything was clean - they even had some toys for the kids. Great location…convenient to all activities, restaurants and hiking trails. We would definitely book again. 5 stars!"

"The house was nice. There was everything that we needed for our stay. The view from the deck was beautiful. The bed was comfortable. The fireplace and hot tub were great"

"Stayed here with my partner during a long weekend. Unfortunately, shortly after we arrived, the weather took a turn and we could not complete our stay. We were beyond sad but will be back asap! Carla has been the most accommodating host ever!!!! She was very understanding and was willing to work with us during the snow storm. The cabin is absolutely gorgeous!!! The cabin was clean, has everything and anything you could possibly need and then some. Will definitely be returning customers. Couldn’t...

"We very much enjoyed our stay at this property. Walking distance to Harper's ferry attractions and plenty of room for 5 adults to spread out. We anticipate renting this property in the future for more ladies weekends!"

SAR 1,501 total

includes taxes & fees

23 Feb - 24 Feb

"We had a wonderful stay at the Riverside cabin. With a beautiful view, perfect deck for reading, and a quiet house to get away in. So close to town and activities provided for a wonderful getaway. "

"The house was a perfect size for my group of 10. We stayed for my birthday weekend and the house was very stocked with cleaning supplies, sheets, pillows, towels, etc. Michael was very responsive and even sent a huge list of recommendations in the area. If I'm ever in the area again, I will definitely be staying here!!!"

Charles Town Vacation Rental | 5BR | 3.5BA | Stairs Required | 5,600 Sq Ft

"Our families decided to rent the property for a getaway close to the DMV. It was easy to check in, get around Charles Town and enjoy the property. Even with an unexpected 6" of snow, we still found time to appreciate everything the property had to offer."

View of High Street in Downtown Harpers Ferry from front porch

"Great communication with host. Cosy house, well equipped kitchen in a great location."

"If you are looking for a mountain house with great views and privacy, this is a perfect fit. All around great experience and I’d like to visit again. "

"Great house! Lots of room and cozy. Even saw some deer! Highly recommend!"

"We got a chance to celebrate our family 40 years of marriage with our family and it was an absolute blast. The host was very detailed in his instructions about the property ensuring we had everything we needed throughout our stay.and available to ensure He did so in a timely manner throughout our stay. The kind women cleaning and preparing the home put in extra time and was so sweat and pleasant as we began our stay. In terms of the property, it was well was well equipped and clean and the beds...

"Is there traffic/road noise? Yes. Can you walk to everything on King St? Also yes. Tradeoffs."

SAR 1,294 total

includes taxes & fees

25 Feb - 26 Feb

"Beautiful cabin in a secluded area perfect for an escape from the hustle. Loved relaxing in the hot tub and sitting by the fire place. I would definitely recommend for a relaxing and recharging cabin experience. "

SAR 15,007 total

includes taxes & fees

8 Mar - 9 Mar

"Our group of seven was very, very comfortable there. It was nice to have two separate living areas one on the upper floor and one on the lower floor where one area could be the quieter area and the other area could be the louder area. Bedrooms were separate from the main living spaces on both the first floor and the basement which was very nice. Price per value was excellent, and whenever I return to the area, I will happily stay there again if it’s available!"

"We made a great choice in choosing the Riverfront Retreat for our Thanksgiving celebration. The large dining table fit our group and its close proximity to the kitchen made serving and cleanup a breeze. One bedroom is set apart from the others which worked perfectly for one couple who ducked out at 5am to catch a flight out of Dulles (about an hours drive) without disturbing others in the group. We enjoyed hiking in Seven Bends State Park and even toured the Shenandoah Caverns (a short drive)....

Chester Gap Vacation Rental | 3BR | 2.5BA | 2 Stories | 1,400 Sq Ft

"The owner communicated well and was very responsive. The fireplace stove was great and we used the hot tub every day. Kitchen was well stocked. We cooked almost every meal and had everything we needed. The office space is a nice, private, comfortable space, as well. "

"It's was great. We visited family in the area. And had our family Christmas together at this place. We played ping pong and pool when we where there. Great location for dogs. Plenty of space to run and play. The house was great as well. Plenty of space for everyone."

"Lovely house. A couple of rooms were cold but not unbearably cold. The large table in the sun room was awesome for Thanksgiving dinner. We would definitely stay again if we wanted a house in the area."

"Family and friends surprised my sister for her 40th birthday with a weekend getaway. Host was very responsive and gave great recommendations. House is in a great location, everything was within 15-20 minutes away. Easy check-in process and very clean. Thanks again. "

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Other property types in Winchester

"My friend and I spent the weekend in John's Cozy Cabin to enjoy some time away from our urban settings and focus on writing in a quiet, secluded place. This cabin was just what we were seeking because it was tranquil, isolated, in serene settings in the forest along the Shenandoah River, and it had everything we needed. John was proactive in his approach, taking the time to discuss our needs and preferences before our stay. His thorough communication and attention to detail ensured that my...