Holiday rentals with outdoor seating in Winchester

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.

I’ve had the wonderful opportunity to stay at Elizabeth’s place a few times and it’s one of my favorites! It is so homey, spacious, and the location is fantastic! Elizabeth is a fabulous host…great communication and very personable. This last stay in late May was very special because my son graduated from Shenandoah Conservatory. Highly recommend to stay here!

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.

Thank you as always for your hospitality and responsiveness! This is our third stay! Highly recommend.

This peaceful cottage is in an extremely beautiful and private setting that is convenient to all that the VA piedmont area has to offer. Perfect for exploring the history and culture around Upperville, the Plains, Marshall, and Middleburg, great as a base for outdoor activities in the scenic local parks and trails, or ideal as a restful weekend retreat to get away from it all. Large, comfortable, and well equipped for a couple or small family.

This is such a special place to stay! The views of the Shenandoah Valley are spectacular, and the house is set up to let you see those views pretty much all the time. The house itself is beautifully decorated, clean, and comfortable, with a lovely working wood fireplace and comfortable seating, as well as lovely bedding and good mattresses. We visited in winter (during a wonderful snowstorm!), but I'm sure this would be a glorious place in all seasons. Thank you, Erin, for being a great host!

Super grateful for Zeb! This cozy little studio was perfect for a weekend getaway for me and the missus. Parking was easy and made unloading luggage a breeze. The place had everything we needed for a comfortable stay, and the location couldn’t have been better … right in the heart of historic Shepherdstown. Highly recommend!

Besides the above, the place had an excellent internet connection with multiple outlets in both the bedroom and living area. Lots of small details throughout that showed a lot of thought went into providing comfort to whoever stayed there. Its appreciated.

We had a really lovely weekend stay at Michele’s apartment. The location was great for visiting Shenandoah national park and restaurants and shops in Front Royal. Super peaceful woodsy surroundings too. We appreciated our host’s many recommendations in the digital guide and in the apartment. Would gladly stay again.

Very peaceful and nice place

Driving back from the funeral of a favorite Uncle and dealing with family drama my soul was craving peace, comfort and a respite from everything for a bit. I found that respite in this Air BnB. The river view was blissful and everything was as described, no hassle and no surprises. Here are some things that I hope the reader finds helpful. 1) You can get the keys from the back porch entrance but bring your luggage up thru the carport door or the front don't try to bring your luggage up that spiral staircase. 2) Bring any silverware you may need and a coffee stirrer 3) The device to the side of the bed IS NOT THE AC CONTROL, lol it is the sleep number bed remote. Check that both sides are set to the same setting before getting into bed. Fun fact: Another guest must have thought it would be funny to switch one side on high and the other side on low. The bed sags on one side if you do that. It was so peaceful, I loved it. She couldn't have been more sweet and delightful.

Such a beautiful place, the yard is peaceful and pristine. VERY spacious apartment/ studio! Comfortable bed!. We had a great stay!

Their place is the cutest! You can tell they take pride in hosting. Will be booking with them again if we are in the area.

Super nice, cozy and well thought out decor. Close to Front Royal downtown and conveniently located close to restaurants and Shenandoah National Park’s North Entrance. Space was just right for me and hubby. The place had private access/stairs up (1 flight or so) to the Apt offering a quiet stay and extra privacy. Would stay here again and def recommend this place!

I wish there was an extra star for the Host! Lorena was super helpful, always responded less than 30 minutes, and made us feel welcome into her home. Personal touches say a lot, and she had written us a nice thank you card that was on the table when we arrived. It was also nice that we did not have to run out and get toiletries immediately as they were readily available upon our arrival. Lorena was also upfront with an issue involving the oven, however there was a toaster oven readily available if we so choose. I highly recommend her condo to anyone with a small group of people/small family that plans on staying in the Deep Creek area!

We came for a graduation and Bill’s space was perfect for what we needed: private, clean, and comfortable. He was welcoming but not intrusive, and we felt safe. We’d definitely stay again!

Large place, great jumping off point and close to town for my partner, my dog and myself. Very clean, and set up great to watch TV at night or work from home. And a fully operational kitchen so you don't have to eat out every night. Thank you again!

Andy was very responsive and gave clear instructions. We had been at this resort a few times in the past and the unit we received was very nicely appointed and updated. We had all amenities and were super close to the indoor pool and gym. Comfortable.

Molly was a great host. The Airbnb looks exactly like the photos. The place was clean and had everything we needed. It was quiet and we couldn’t hear any neighbors. Molly gave very detailed instructions which made checking in super simple. The beds were a little bit hard but other than that, this was a perfect place to stay.

We had a peaceful stay. It was quiet, clean and all house instructions were detailed and easy to follow. Communication was good and efficient! So much nicer than any local hotel 😊

This was a great spot! Definitely will stay again the next time we are in town. The location is amazing!!!

Immaculate!! This is the cleanest AirBnB I've stayed in. Fully stocked with extra linens and pillows, snacks (what?!), every utensil and kitchen item you'll need, too many pluses to list. The back yard looks like a private forest, the house is so quiet and cozy, and close to gas stations, grocery stores, restaurants, etc. You'll love staying here :)