Family-friendly holiday rentals in Holmes County

Fantastic spot! PERFECT if you are with a couple of friends or looking for a convenient place so you can bounce around downtown Wooster!

My friends and I have made stopping at the Penthouse an annual kick-off to our summer on our way to Sandusky. Rob is incredibly kind and friendly and even happened to see us bringing in our luggage and offered to help carry them up. Wooster is such a charming little town with lots to do (cute shops, lots of great restaurants/coffeeshops, etc) and the space made us feel right at home, so much so that on our first visit we decided to come back over and over.

We had a wonderful time, the place was very clean, described accurately, and easy to find. We found most everything we needed and loved the huge deck, the jacuzzi and the lovely swing down by the river. Since we only had one car, we were unable to take advantage of the kayak, but there was plenty of other things to do nearby. Thank you for a very peaceful and fun few days.

We really liked the place and Amy is a nice and attentive person who welcomed us well into her home, we would definitely return

To keep it short & simple.. everything was fabulous. Owner seemed very nice. Very helpful and responsive with any questions. They gave us complete privacy but made sure we knew exactly how to reach them if we needed ANYTHING. The cabin is very organized, labeled, clean, ect. My personal favorite was the screened-in porch. Really appreciated the fact that they left a large wagon right where we park so we could take all our things to the cabin in one trip. Would highly recommend!

We definitely enjoyed the beautiful cabin and grounds, as well as the Pool Table, Slot Machine, Golden Tee Golf Game, Theater Room, Hot Tub, and all the other amenities. The beautiful Peacocks and Cats were also great to see. The Scavenger Hunt was enjoyed by all our guests. Alan and Laura were very responsive to our needs and are great hosts. The cabin was well stocked with anything we needed and we had a great time.

The stay was all we had hoped for. Plenty of space for our group of 14. Fishing was great for the kids and plenty of space to play in the yard. Highly recommend.

Our party had a lot of last minute changes and adjustments, but Rob was very communicative and easy to work with.

Lynn was immediately available for our arrival and gave a thoughtful tour of the place. The kitchen was well stocked with food for breakfast and delicious coffee and treats. Her farm was out of the way and very peaceful. I will be back to stay again soon!

absolutely loved our weekend away! Jan is amazing and accommodating. so very friendly.

We had a great stay at the 3 Tree Chalet. An absolutely beautiful property. The kids ages 6-13 had the best time playing in the lake, fishing, playing pool and having bonfires. House was perfectly stocked and had everything you could ever need. We are hoping to make this an annual trip. Thanks for a great long weekend Ian!

Beautiful home, it was lovely to be able to relax in the back yard and let the dog run around after a long drive!

Great stay! The house reminded us of a real-life Clue game with “secret” passages that connected each room. They did an amazing job of modernizing things enough to be functional, while still honoring the historic nature of the house. Breakfast and fresh fruit was such a nice touch and we are so grateful!

The beautiful Woodbury Cabin and Pond is super peaceful, quiet and makes it easy to just… PAUSE. Highly recommend!

Very peaceful with plenty of indoor and outdoor space We stayed for a Thanksgiving gathering in New Philadelphia and the property was very convenient and Kari was so friendly & helpful Would love to rent this property in the summer months! Thank you

Our stay at The Lodge on the Hill in Sugarcreek was amazing. It is a wonderful place for family/friends to spend quality time with one another. This is the 3rd time we have stayed at The Lodge-it never disappoints. The amenities are plentiful, the view beautiful and the host is readily available. The Lodge on the Hill is highly recommended.

Cabin was beautiful as promised, loved that we didn’t have a full set of check out cleaning rules, very clean and had everything my family and I needed for our stay!

Jeff's place was amazing, so much we booked another night. we will definitely come back again! Jeff was very helpful, he answered any questions we had. I highly recommend his place!

Visited with our whole family as a surprise gift for our parents 50th wedding anniversary. Loved we had the entire place to ourselves. Fun, unique stay. Tom the Turkey was a family favorite. Loved all the animals! Trails were great; especially the view from the top overlooking the whole valley area. Pool area and ping pong were fun! So convenient that we didn't even need to bring pool towels. Plenty of space for outdoor games. Enjoyed the Farmhouse porch and playing cards inside as well. They even provided an extra card table and chairs when we mentioned we would be playing euchre. Kitchens were well stocked with anything we needed. Barn house had so much character! Super Cozy!! Air Conditioning worked great in all 3 places. Hosts were very nice answering all our questions and chatting about the farm. Would love to come back again sometime.