Family-friendly vacation rentals in Winchester

We enjoyed our time and the hot tub was great. Truly peace and quiet

It was very peaceful and was a great getaway for me and my boyfriend. We enjoyed the area and the cabin. Everything was perfect! We’ll definitely be back

Quiet, peaceful, private. Very helpful with a special request that was made. Recommended.

This was my second stay at one of Derek’s cabins, and just like the first time, it was absolutely perfect. The cabin was peaceful, secluded, and surrounded by the natural beauty of the Shenandoah area—exactly what I was looking for. The views from the hot tub were absolutely extraordinary, making it the perfect place to unwind. Another great perk is that while the cabin isn’t directly on the river, it comes with access to the community’s river access, which is an awesome bonus. I’ve had such great experiences with Derek’s cabins that while I was here, I went ahead and booked another one for May! That’s how much I trust his hospitality and the quality of his rentals. If you’re looking for a quiet retreat in the Luray area, this is the place.

This was the cutest little place for my little birthday getaway with the hubby and puppy. Thoroughly enjoyed the hot tub, the fire pit, and the grill. Relaxed a lot and made great memories. Worth every penny!

Jackie’s cabin was exactly as advertised; peaceful, secluded, with beautiful views of the starry sky. Very well appointed kitchen, and lots of room for lounging in the living room. Would recommend for anyone looking for quiet time away with high speed internet.

The Rock Cottage is a perfect romantic getaway! We enjoyed walking all of the hiking trails and exploring the vast property with our 2 dogs (such a treat when they can vacation with us). The wood burning stove and hot tub were wonderful amenities on the cold weekend. It was an easy drive into Culpepper for a fabulous dinner at Piedmont Steakhouse (pricey but worth it). And, our favorite part was the Pool House/Spa, the pictures do not do it justice. The Steam Room/Sauna/Cold Plunge/Sauna regime was rejuvenating and being able to swim in the deep. vast pool with attached hot tub completed a perfect afternoon. On our way home we drove 15 minutes out of our way to visit the Copper Fox Distillery and adjacent shops in Sperryville - a must if you like craft whiskey. We are looking forward to returning during a warmer season to enjoy even more of what the grounds have to offer. Thank you Connie, Paul, and team for being so responsive and helpful!

We had a great time at the cabin! It's a beautiful spot right near the river, and Angela has clear instructions on how to access it. The winding road to the cabin made for a beautiful sunset run, and the hot tub was so peaceful! We also enjoyed being close to the Luray Caverns, which was an awesome day time activity. We also appreciated the TV/speaker set up and full kitchen with pots, pans, and cutlery all ready to go. Angela was also very friendly and ready to answer questions whenever they came up. Highly recommend!

This is our second time staying here and third time staying in Kimberly’s rentals. We have been completely satisfied and will continue to visit staying here! Very quick on responding to messages with a positive response. Such a great place for a getaway. We will see y’all soon!!!

The Nest is nothing short of magical. Perched high above Chester Gap Valley, it feels like a slice of paradise—a serene haven wrapping you in a warm embrace. The calm, comfort, and peace are amplified by the rolling hills and tranquil surroundings. If you're escaping the hustle of DC or seeking a refreshing retreat, this is it. Julie is the epitome of a gracious host. Her warm hospitality shines through every detail of this impeccable home. Beyond its pristine cleanliness, it exudes charm and character, showcasing the care and love poured into crafting this beautiful space. From the unique decor to the thoughtful touches, it's not just a stay—it's an experience. As we departed, our spirits felt lifted, refreshed, and inspired. Without a doubt, this was one of our best Airbnb stays. We will certainly return. If you're scrolling through listings unsure, don't worry—you'll just *know*. Trust your instincts; The Nest is the one.

Melinda’s apartment was so homey and inviting. We loved spending time here. It was the perfect place to relax and a great jumping off point for all the sites we wanted to see. The neighborhood was quiet and the space had everything we needed. We would definitely stay here again!

We spent a long weekend at David's home with our two pups and couldn't have enjoyed it more! The property is very private, you feel like you are on your own mountain, and is so peaceful and quiet. It was a rejuvenating trip and we would definitely love to come back in the future.

Beautiful location and very cozy. This is our third time staying here. We love it

We had a very nice 3 day weekend at Elizabeth's place. The house was really cozy and we felt relaxed and at home there. It was a great location to reconnect with family as my brother and his wife only had to drive an hour from DC area to spend time with us. We enjoyed being able to walk from the house to downtown for lunch at the Box Office Brewery and antiquing at Strasburg Emporium. On a sunnier day, we had a great hike at nearby Elizabeth Furnace Recreation Area. Something for everyone in the area!

Oxana and Jeff were responsive and friendly. The place was easy to find with ample parking. The interior was spotless with plenty of space to lounge. Oxana provided lots of local recommendations. I would stay here again without hesitation!

This place was our best choice even before we realized there would be a freshly-prepared, multi-course gourmet breakfast. House is as advertised, clean, and well-located. Scott and Lisa are friendly, responsive, and fantastic cooks. Enjoy!

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.

We stayed at this charming home during our recent family ski break. The home is extremely clean and exactly as pictured. Jo was very friendly, helpful and responsive. We loved the location. It is a few minute drive to base camp and walkable to the playground (huge plus with our kids). Each evening we could see deer just a few yards away. We would definitely stay here again and highly recommend to anyone considering this house.

This was our third time staying at Gigi's Mountain Cabin. It was fantastic, as always, and we look forward to coming back next year - if not sooner

Our family of four spent two nights at Callie's Cottage. We had a great time enjoying the trails, fishing the pond, and watching the horses. Our kids had a lot of fun playing in the treehouse. The house was cozy, clean and well appointed.

A beautiful and peaceful location just as described in the listing. The sunrise in the morning was beyond words beautiful. We enjoyed the hot tub access after spending the days hiking - entering only after showering of course. I wish we had one more day to explore the property further. We hope to return in the fall. The kitchen was well stocked with spices and dishes. We didn't do much cooking but would not have needed much more than the basic groceries for meals. We appreciated the green practices that are in place with composting and no plastic bags. We essentially treated it as a 'leave no trace' as we often do but it's nice to see the commitment this farm has to these practices. The bed is a bit on the soft side in case you are a firm bed sort of person, you might find yourself on the daybed which is more firm. Overall, we were very happy with our stay.

As many have reported this is a true gem!! The view is to die for! We spent one day biking to Luray from Rileyville. A stunning country road ride with farms all around, mountains on either side, no cars on the road! Would not recommend biking on overlook drive due to gravel.

This was our 3rd year renting their Potomac Overlook home for our family Thanksgiving and once again, our entire family loved staying here! The home is spacious with plenty of bed- and bathrooms plus super-comfortable beds. And the property is absolutely beautiful with its Potomac River-front location and plenty of very usable outdoor space. We highly recommend it!

Incredibly grateful for this home and for the KOA next to it! We knew we were booking a home with lots of bedrooms a hot tub (the most important things!) but we had no idea it offered so much more. A working fireplace when we got snowed in, a KOA with plenty of activities literally next door, a stunning walking path that we took through the snow when we got snowed in, and an incredibly kind crew who helped us get our cars un-stuck. If I had to be anywhere during a snowstorm, it would be here. And if I had any questions, the KOA was there next door to answer them. Super easy. We were walking distance to tubing, a six minute drive from historic downtown. We just have to come back when the weather is nicer to take advantage of the mini golf!