Kid-friendly holiday rentals in Orange County

We stayed there for a family wedding so we could all be together instead of in hotel rooms. It was wonderful. Lots of bedrooms and places for family time and a fully equipped kitchen.

We absolutely loved our stay. The whole house is an adventure of discovery when you first arrive, much like visiting grandma's as a child. It's beautifully decorated – appropriate to the historic and bucolic surroundings it resides in. It feels as if the love of the family who lived there has included you and cares for you. We enjoyed viewing all the small treasures of history and felt relaxed and comfortable. Suzanne was kind, attentive and informative in perfect amounts. She is a perfect host. Book extra days so you have time to experience all the places to lounge and visit without the rush. We are already talking about when we can come back to tour more of the area now that we know just how centrally located the house is to so many historic sites.

We had a great time at Greg’s and Nicole’s place! I highly recommend it. We especially appreciated how well stocked the kitchen was, as it is somewhat rare to find when staying at a rental.

Excellent place and excellent host.

It was a beautiful property and we enjoyed the outdoor sauna! The house was extremely clean and felt super comfortable. We wished we were there longer to explore the property and trails more but hope to come back on our next trip!

This is a really lovely space, secluded and beautiful! I really liked all the art and design inside the house as well. Beds were super comfy and of course the suspended net was a big hit with kids. We would love to stay here again!

Two of my girl friends and I were in town for a wedding and needed a place to stay for the night. This was perfect! It’s on Main Street, which is adorable. We highly recommend going to Cake Krums for breakfast which is only a 2 min walk. The hosts were very flexible with check-in & check-out times which we very much appreciated. Highly recommend staying here when visiting Madison!

We enjoyed our stay. It was conveniently located for niece's wedding at the nearby Renback barn and for visiting our in-laws in Orange Virginia. The three bedrooms worked well for our family of four. The kitchen with the salad master cookware pots was definitely a plus. We enjoyed the bowl of various tea bags.

Irene is amazing and so is her home on Lake Anna! Great space with privacy and access to lake and amenities. Irene went above and beyond - even coming to pick us up from dinner when our Uber cancelled on us. Such a great experience and highly recommended staying here!

I stayed with Barbara for 3 months and it was great. The place was sparkling, close to town, and Barabara knew of tons of things to do. I would highly recommend.

Jennifer’s place was amazing! A fully private guest house with tons of space and well stocked. Beautiful location and we were excited to use the hot tub. Would definitely stay again when visiting Shenandoah.

The host has always been so communicative and welcoming. Great experience

Carlene and Allan were very kind and generous with the basket of goodies they provided, fruit, cereal, and a stocked fridge. It was so thoughtful and I was truly touched, especially since we had 4 kids with us. They gave us a quick run down when we arrived. We felt very comfortable in their space even with it being on their property. The address takes gps to a driveway that is a little down the property but it’s easy to navigate your way to the actual Airbnb space. I have already recommended this location to friends and family who visit Virginia often. We would stay again.

Renate’s Barn apartment home was a lovely get away from the city life. The whole place is very charming and has tons of space. The host was also very responsive and helpful with our questions. I would definitely recommend and would love to visit back again!

If I could give Jennifer’s place more than 5 stars I would! The property was at the end of a seasonal road so it was very quiet. Jennifer was nice enough to leave us some eggs from her chickens that were delicious. Great place to stay if you’re trying to get away from the city for some peace and quiet

Virginia is a very nice woman and she did her best to be accomodating. What I will say is this... READ THE HOUSE RULES at least 6 times and truly decide if you want to deal with it or not. She really does mean completely "chemical" and scent free everything...it affects her health negatively and she even has a digital monitor of the air quality that she looks at. I did my best to follow the rules and still ended up making a mistake. Don't use a scented laundry detergent like I did by accident. Future guests, you're welcome in advance for the advice..and Virginia you're welcome for me doing my part discouraging any other guest using scented laundry detergent either.🤷🏻‍♂️ If you stick to these guidelines 100% then you'll definitely enjoy your stay. The place is very very clean and quiet.