Family-friendly holiday rentals in Orange County

This is a lovely farm with several cottages and homes available for stays. The grounds are spectacular with pastures filled with horses, gorgeous ponds, and amazing landscapes. The servants cottage met our needs perfectly. We stayed for only one night while traveling home to NY after snowbirds a couple months further south. I have family nearby and hope to stop here again in the future for a longer time. The cottage was well kept with a BBQ grill that my husband happily made our dinner on! There was also a portable fire pit that we enjoyed while having our after dinner cocktails. Super responsive and helpful! We highly recommend staying at this farm and can't wait to go back.

Our hostess, Tina, was easily available over a call or chat. The place is located at a serene location with a lot of horses around. We fed a few apples to the horses and the kids really enjoyed the whole experience. We also used the firepit under the open wide sky, it was very cozy. Gordonsville town was just 10 mins drive away with amenities like gas stations, 7-Eleven, Foodlion, etc. The house is beautifully decorated and has all the listed amenities. While we were cutting my nephew's birthday cake, our dog slipped into the master bedroom and damaged the comforter on the bed (a 3-4 inches long rip). We informed the same to Tina the next morning and offered to pay for the damages but she was very polite with us and mentioned that such incidentals are usually included in the cost and she'll let the owner know - if needed, he'll contact me. We really appreciate this gesture and would highly recommend their place for a beautiful holiday experience.

We really enjoyed our stay! Keith and the team were so kind and helpful.

We had a lovely second stay at Wildwood! Accommodated two families with several kiddos easily and comfortably. Space is private with beautiful views of mountains and near a number of wineries and interesting things to do (one day we visited Monticello and another day we drove into Charlottesville, for example). Super cozy inside with tons of places outside for kids to run around. Great experience all around.

Fantastic place to get away. Thanks for hosting

This was our second time to the farm and I can not think of a better way to welcome the New Year with our children and grand children. The kids LOVE the farm and everyone we encountered couldn't have been nicer. We walked along the farm road everyday feeding carrots to the horses. There were babies this year as an extra bonus. ALSO on one of our walks we came upon a heard of PUPPIES! Small children and puppies couldn't have been cuter. The house was decorated for Christmas so we could put our presents under the tree for our belated family Christmas. Everything was amazing. Our Host Tina responded quickly to everything we needed. I hope we get to return soon.

We wanted a last minute hike and a place to stay nearby. There wasn't a lot left that wasnt booked up and there were many places that charged $60-$100 cleaning fees making the total close to $100 more than the actual nightly price listed. That was not the case here. This place was absolutely beautiful. It was easy to find and we felt right at home inside. Communication was excellent and while we mostly hung out inside after our long hike, there is plenty to do on this farm! I would recommend this place to anyone. We will definitely be staying again.

We loved staying at this farmhouse! It was peaceful and relaxing. The house was as described and pictured. Jennifer was very friendly and responsive when I accidentally locked myself out of the house. She also left us a lovely treat upon arrival. The bed was comfortable and we slept well. We would stay here again.

We were transported into another world when we stayed at this Air BnB. We truly felt like we were on vacation from our daily lives; we unplugged and reconnected as a family. The cows were so lovely; they give such a sense of peace and are an important reminder about how our food is farmed.

Great getaway location with beautiful views and plenty of space to enjoy and relax for a few days.

Sweet place — lovely neighborhood, perfect for an early evening walk. House was spotless and well equipped. We almost could have spent our whole stay in the Adirondack chairs in the back yard.

Susanne is a caring & friendly hostess. So happy we lucked into this special place, thankful there was a cancellation. It was perfect for our group as was the location. No detail was left undone from the well appointed kitchen to the comfortable beds. Tranquil. Felt like home. Looking forward to returning.

Our family and friends had an unforgettable stay at Monrovia on Main for our 40th Woodberry Forest School reunion. This grand, beautifully restored 1904 home was the perfect gathering place! The location on Main Street is ideal—an easy walk to downtown Orange's shops and restaurants. The home itself is exquisite, with elegant antique furnishings, luxurious bedding, and updated baths offering modern comfort. We especially loved relaxing in the spacious parlor and game room, and the front porch was the perfect spot for afternoon naps. The gardens were stunning, with azaleas in full bloom. Everything was meticulously clean and thoughtfully prepared. With five lovely bedrooms and a large, well-equipped kitchen, we had ample space to reconnect and relax. Gaines was a wonderful host—welcoming, responsive, and attentive. We couldn't have asked for a better place to celebrate such a special occasion. Highly recommend Monrovia on Main!

Irene is very responsive and helpful. We spend a great weekend with family and friends! We did kayaking and fishing. Irene provided great advice to us about how to find the best fishing spot. The house is clean and beautiful. The nice patio also includes a gas grill for who wants to BBQ. THIS PLACE IS HIGHLY RECOMMENDED for who want play around water! Definitely will come back.

Great getaway location with beautiful views and plenty of space to enjoy and relax for a few days.

We loved the house and its location. We enjoyed the kayaks and the fire pit tremendously. Sunrise was beautiful as was the full moon rising. Our host Christine was pleasant and responsive and informed us the house was ready early and we could check in early! We will definitely return! Our pups loved running around the yard!

Sweet place — lovely neighborhood, perfect for an early evening walk. House was spotless and well equipped. We almost could have spent our whole stay in the Adirondack chairs in the back yard.

Beautiful apartment with thoughtful touches everywhere! Super helpful hosts. So lovely to enter and find a bottle of local wine and locally baked goodies. Comfy robes, plenty of towels. The location features an amazing view of the Blue Ridge. We loved sitting by the fish pond with some wine and enjoying the rolling hills.

Excellent place! We enjoyed our stay. Very clean!