Vacation rentals with outdoor seating in Winchester

We had a wonderful stay at Ken's beautiful cabin - it was clean and well-equipped with lots of thoughtful touches. The surroundings are gorgeous and we enjoyed hiking around the property, visiting with the chickens and bunnies, and playing in the stream and nearby lake. We felt relaxed and at home, and we would highly recommend this listing if you are looking for a peaceful getaway!

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!

The place was super cozy and made for a nice peaceful weekend away in wine country. It’s also a great location to take day trips out! I would come back again with a bigger group as and try out the other houses on this property.

This is our second stay here, we love it! Very clear instructions, and the perfect place with everything we need.

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.

Really amazing place. The back deck and backyard are super nice. Also a great view in the backyard

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!

Great stay! Comfortable and clean, very convenient.

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

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!

Our stay was very convenient and comfortable for our competition weekend. I appreciate that the place is pet friendly. It was clean and organized. Thanks so much.

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 thoroughly enjoyed our stay at Occoquan and the Daisy. The location is great and within walking distance to eateries and shops. We enjoyed Grind and Crepe for most of our breakfasts as they open early. Nice shops. It was nice that parking was available. It was quiet outside. The only thing I would mention is that we did hear footsteps at night from whomever was upstairs. I would stay at the Daisy. again. We loved our stay.

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

Had a great stay! Taylor was super helpful when we needed to change check in date. Beds and couch were very comfy. Felt like home!! My husband appreciated the fresh coffee beans/grinder! My daughter loved the snacks! Very close to shopping/restaurants. Will stay again!!

We really enjoyed our weekend getaway here! Lourdes was super responsive and we felt right at home throughout our stay. Beautiful surroundings around the property. Highly recommend and would definitely stay again! :-)