Cottage holiday rentals in Winchester

From the first step inside, felt right at home. Fully stocked kitchen and the place was spotless. Definitely a 10 out of 10. Was a bonus having such an amazing view of the mountains and cows. Do yourself a favor and book this location!

Elizabeth Cottage is an absolute gem! The home is cozy, comfortable, and filled with sweet touches that made our stay lovely. The yard is large and so pretty, with nice outdoor seating spaces to enjoy the garden and birds. We loved being so close to the springs, baths, and shopping. Everything inside was top notch and completely ready for our arrival. Thank you for sharing your beautiful home with us!

The house was comfortable and I loved that you could hear the creek from the house with windows open. We’ll definitely be going back!

We had a great stay! Olivia was an excellent host. The place had the perfect vibe for a girls weekend and birthday celebration. The only issue we had was needing to catch 2 wasps that were in the house, but we were able to take care of that without issue. It was so nice to have so many towels and amenities that you don’t normally have in an Airbnb. Thanks again!

Darrel went above and beyond in making sure we had a great stay! He was kind, responsive and overall a superstar. We had an incredibly relaxing time and enjoyed the peace his listing had to offer. An EXCELLENT way to spend some time away from the city. I hope to come back soon! Couldn't be happier with Darrel's service!

So comfy and clean! Stayed for a few nights with some friends to forget about life for awhile. Easy walk to town, awesome hot tub on the deck and the grill works great. We left recharged and will def be back!

I had a wonderful stay at Chris and Sandy’s farm guesthouse. It was very easy to find and exceeded my expectations. They were the best hosts and I would definitely return. I especially loved feeding the donkey, Jasper. Sandy and Chris went out of their way to make it feel like home for us. Thanks again for the Yoder’s icecream recommendation, we loved seeing the free petting zoo.

We really enjoyed staying in this cottage. The patio and deck were great, we enjoyed the hot tub multiple times! Lots of games to play which was so nice. Nicholas was responsive when we had questions and very friendly. We really enjoyed Lost & Found Pizza & Provisions as well as Mack’s Bingo Kitchen based on his recommendations as well! Overall great experience!

It's a great location and the house is well-stocked with anything and everything you could possibly need.

Jen's place never disappoints. Peaceful and secluded but close to so many things for entertainment if thats what you want. I enjoyed just settling back and relaxing.

We had a wonderful stay! The property was a great deal and exactly what we were looking for — peaceful, private, and secluded without being too far from everything. The location was perfect for a relaxing getaway. The host was incredibly friendly, responsive, and proactive, which made the whole experience even better. The listing description was accurate, everything was spotlessly clean, the AC worked perfectly, and check-in was super easy. We would absolutely stay here again and highly recommend it to anyone looking for a quiet, comfortable place to stay!

Susan’s place was full of thoughtful touches like wireless phone chargers, a basket of various charging cables and even some Easter treats and a smores “kit” to use at the fire pit. Perfectly situated for a visit to Luray Caverns and Shenandoah National Park. Great hot showers, fluffy towels and comfy beds. Well equipped kitchen and outdoor deck area for outside dining, with gas grill were appreciated. We thoroughly enjoyed our stay!

The cottage/house was as described and wonderful. The location was perfect to explore the many nearby hiking and outdoors options. The property itself has an excellent view. The fenced in yard was convenient for our dog. Inside everything was clean and well-maintained. There were a number of nice touches to make you feel at home. There was everything one would need and more. I needed to work remotely one day and the WiFi was very reliable. Great stay!

It was a very nice place. The fire pit was great. We got to sit around the first night. A cottage was very quaint and clean. Will use it again and lots of extra things for us to use when we ran out of like the water thank you, Michael.

This was our third time staying here and it is always wonderful. The property itself is beautiful and peaceful. Our dog loves the fenced in yard and dog amenities (water bowl, poop bags). The coffee that Billy provides is so good and much appreciated. Phone coverage can be spotty (the provide wifi works great), so the recommendations and directions provided in the Welcome binder are very useful. Love it here & hoping we will be able to visit again soon.

Such a find! Sandi's place is peaceful and secluded and yet convenient to Middleburg and Oak Spring. There is so much to do locally, from the antiques stores to hiking to the vineyards and breweries. Sandi was a fabulous host - proactive and responsive - and the cottage is well set up and very comfortable.

WE had a lovely weekend stay at Bret's place. It was a cold, snowy trip but we still took long walks up the road and watched the snow fall with a roaring fire. Bret did a good job reaching out to make sure everything went smoothly. The kitchen is quite small but has everything you need to cook some good meals. Would be a cool place to visit in warmer months with the lovely creek right outside the front door! Do note the water is pretty smelly so you can do everything with it but drink, but there is plenty of drinking water provided.

Fishback cottage was a great location for us to stay while visit town for a wedding! Gorgeous front porch to sit on and have your tea/ coffee! Flexible, helpful, and responsive hosts!

Kay takes pride in this property and it shows in her attention to detail. It is a lovely place to stay and she personalizes the experience to make you feel welcomed. The home is well decorated and super clean. We loved our stay!

We had a lovely stay at this cottage. Very clean and nice amenities. 25 minutes from White tail and 15 minutes from downtown Mercersburg. Super friendly hosts.

The house and property were beautiful, the house was super clean and felt cozy even though it’s new! Check in was really easy and Zeb was quick to respond. Loved being able to sit outside at the fire pit! It was a 10 minute drive to Shepardstown and 30 minutes to Harper’s Ferry so we were able to explore and go to some of the places that Zeb recommended! Highly recommend!

We had a great stay! This is the CLEANEST Airbnb I’ve ever been to. Very beautiful area and scenery, and perfect distance from Luray Caverns and Shenandoah National Park. Valerie was very responsive and helpful when needed. The only suggestion would be to take a car that can handle a somewhat steep and rocky driveway.

My husband and I decided on a last-minute weekend getaway, and Bonnie was so accommodating with this gorgeous little cottage! The space was clean, comfortable, thoughtfully furnished, and the kitchen had everything we needed. The historical details were one-of-a-kind. Absolutely loved the quiet setting on the family farm and close proximity to the brewery, too! I would highly recommend this space - it's the perfect location for exploring wine country.

We loved every minute!! More spacious and comfortable than we had anticipated !! Kelly and Diana are wonderful hosts! We had such a relaxing and wonderful time! We highly recommend it to anyone who appreciates beauty and relaxation! And did I say the beds are super comfortable?! Best Airbnb I have ever stayed in:-)!