Family-friendly vacation rentals in Winchester

Our stay was private and cozy. Loved the hot tub. No spiders inside, unlike the last place I stayed at.

This is our second time staying at one of Laura's properties and each time has been terrific! What you see is what you get... a large fully functioning home with easy check-in, nice amenities, responsive host and easy check out! My family and I had a great time, thank you Laura!

We loved our short stay at Mason’s place!! We needed a peaceful getaway to just relax and it’s exactly what we needed. The hot tub was amazing, and we hiked all around the property and campgrounds! Had so much fun connecting with nature and relaxing. Also loved how many amenities, spices, oils, pots and pans, etc in the kitchen!!

My husband and I enjoyed our stay here very much. The check in process was easy, views were great, hot tub was nice. Only complaints would be the bed as it was not comfy/very squeaky. We would definitely consider staying here again next time we visit Shenandoah National Park.

Excellent stay! Beautiful locale! Would stay again for sure!

We love staying here. This was our third time. It’s a great area to explore and the house is super comfy. Lounging on the deck is the best part.

The only part of the stay that didn't get 5 stars was that it wasn't quite as secluded as I'd hoped for. There are a number of homes on the road to the cabin, and a thin line of trees breaks the view. Admittedly unless you're looking for the other houses you don't notice them, so I got past that quickly enough. That said, the cabin was perfect, clean, cozy and everything worked as stated. Having grown up in the country, but living in a city now, I felt the stress melt away as soon as I stepped into the massive yard where my son and I spent a lot of time playing soccer and other sports. My son and wife really enjoyed the hot tub. The location is 15 minutes away from Luray which meant that the stars were amazing for the brief break in the clouds we got, but that it was close enough to get groceries and take out as needed. Plus it's about 20 minutes away from Front Royal so there are places to go and enjoy like Skyline or Luray Caverns. Jackie was a great and responsive host!

I have now stayed at 3 of Derek's properties and all experiences have been fantastic! I think I loved this Walden cabin the most, though! The view, the gorgeous property, the well-kept and comfortable home - it's all amazing. I don't think I'll stay anywhere else when I want to visit the Blue Ridge from now on!

Couldn’t have asked for a better place for a girls weekend! The view was better than the photos, peaceful and comfortable!! I HIGHLY recommend this place!

Julia's place is an Idyllic setting - so tranquil, yet close enough to a great tavern for dinner. Amazing - we cannot wait to come back.

We have stayed at this home many times because- a.) They have a fenced-in backyard so it is nice to be able to let out our dogs without worrying about them running away and b.) we love hiking at Lost River State Park which is just a short 12 minute ride to from the house, and c. It is a beautiful quaint home- very peaceful and has all the amenities we need.

Jonathan's place is wonderful as always. Had an exciting weekend to disconnect and enjoy good company in beautiful scenery. Look forward to coming back!

Tara and Shawn were great hosts! The place was comfy, they were easy to communicate with, and great of all, we got to hang out with their awesome goats and feed them snacks!

The house was so uniquely quaint! It was truly a time to unwind from the craziness of this world! No TV other than in the upstairs bedroom and no Wi-Fi, which made it so nice to “unplug”! The sauna was absolutely amazing! The two options of fire pits to relax and have s’mores! The fireplace in the main living room was such an added bonus, to take the chill off in the morning and to just have a nice fire in the evening before bed. The fact that they had food there for us for breakfast was truly amazing! A bottle of wine to share, which was great considering we were there for our anniversary. You can get to so many places within 20 to 40 minutes! We went into Harpers Ferry for dinner at the Rabbit Hole! Harpers Ferry is a must to visit if you are in the area! Tons of trails, white water rafting and things to see and do are all just a short drive away. If you want a place to truly unwind, this is it! 🥰

This was our second time staying here. Nice and private. Great hosts.

Our trip was absolutely flawless. Maureen is a gracious host who has an amazing place in a perfect location outfitted with everything you could want or need for getting off the grid for a while. We can’t wait to go back! 100% recommend!!!

Absolutely loved our stay at Brad's! Place was clean, check-in and checkout was easy, and Brad was super nice. Would definitely stay again ❤️

This was our second stay at Janel's place and it was just as enjoyable as the first time. We loved the fireplace and views from the A frame windows. The hot tub wasn't working unfortunately, but things happen and Janel was communicative about it. Had a great weekend regardless. Also love that Janel is accommodating of dogs. Our fur babies were happy to join us on our getaway.

Cute little place on a stunningly beautiful property! Our host was always responsive. We'd love to come back!

We had a wonderful getaway at Seths place in Rockingham. Perfect location for a group of 12 girlfriends that wanted to relax. Loved the pool and the porch/patio! Felt like Tuscany. Seth and Carla were extremely responsive to the couple of small issues we had. Definitely recommend.

We had a wonderful stay at this cabin! Close enough to all the hikes we wanted to do. Pet friendly (huge for us) and beautiful views! Please make sure you read the whole listing, as you definitely need a vehicle with 4 wheel drive to get up the driveway. We brought our own towels, sheets, and so on as stated and everything else we needed was available. Would recommend bringing dish towels. We had forgotten them this trip. Cooking pots and pans are little outdated but they’re just fine! We had a wonderful taco night anniversary dinner at the cabin and throughly enjoyed a nice soak in the hot tub. There’s a very nice above ground pool also but it was too cold this time of year to swim in. I would definitely stay again!

We had a wonderful family reunion here with 3 generations. Each family had their own private space but there was tons to do on the property together as well. The hosts were very responsive to our questions and made sure we were comfortable and happy! We appreciated that the kitchen was well stocked, too.

My husband and I stayed here right after we hot married and it was the most lovely experience! It was an absolute blast, I wouldn’t have changed a thing except I wish I could’ve stayed longer. Maud was so sweet and I loved having her as a host. Cannot recommend enough!

We had such a lovely weekend at the yurt with our kids (10 and 5). Being surrounded by the woods and mountains is so peaceful. We cooked all our meals in the well stocked kitchen and the kids enjoyed the loft area. Beds were comfortable and hot tub was a treat. My kids said we should give the place 8 stars (out of 5!).