Family-friendly holiday rentals in Wooster

TheLegacyHouse: Historical Suite Close to Downtown

Welcome to The Legacy House Wooster! This is a charming Victorian home within two blocks from the wonderful downtown attractions, shops and upscale dining. Our grandparents' love for people and hospitality inspired us to create a warm and inviting home where we could share their legacy and traditions with others while restoring their historic home back to it's former beauty. Experience all the amazing opportunities Wooster has to offer while enjoying a unique, comfortable home to relax in!

Family · Indoor spaces · Decor

Your 2nd Home Away From Home l Prime location

This is a fully furnished apartment that has all the amenities of home. It is an updated apartment in an older home, but thoughtful touches and attention have been taken to make this feel very comfortable and relaxing. You'll be pleasantly surprised with the atmosphere and the space that you'll have while staying here. The apartment is conveniently located within a couple short blocks of the college, and just a short distance to the wonderful downtown Wooster with plenty of shops and dining.

Family · Indoor spaces · Condition

Cozy Abode

The space is a dedicated basement apartment. The space has its own door and lock, but guests will enter through a shared garage entrance. The decor is neat and modern. There is a small kitchenette, giving guests the ability to eat in, or make coffee. The cozy sitting area is a great place to wind down for the evening or enjoy a morning cup of coffee. The apartment is below our living space. While we will do our best to keep noise to a minimum, you will hear kids/footsteps during the day.

Kitchen · Family · Decor

Meg's Lucky Buckeye

We have revived the unique character of this old house, built in 1864. The floors aren't level - some of them creak - but the details are lovely, and generous light fills the rooms. In keeping with our other rentals -- we are pet friendly. Our daughter is a College of Wooster alum and that's what brought us to Ohio - she stayed. I named the house in memory of my mother, who never set foot in Ohio but always believed buckeyes are lucky. We feel lucky to have found it; hope you do too.

Kitchen · Indoor spaces · Comfort

Welcome to The Cabin at CT Farms!

Tiny-home, located on our 5.5 acre farm in western Wayne county. This brand-new cabin was constructed by local Amish builders. Complete with most amenities you'd find at home, it offers a cozy spot to relax or work. Have a cup of coffee on the porch and listen to the farmland awaken, or catch amazing sunsets in the evening. Located 2 minutes from US Route 30. 1.25 hours from Cleveland/Columbus. 10 minutes from College of Wooster. 30 minutes from Amish Country. (Berlin/Millersburg).

Family · Kitchen · Parks

Bonnie Jane House

The Bonnie Jane House is a family friendly space on a quiet, tree-lined street, within sight of the College of Wooster and minutes from downtown. Perfect for college, business, and local tourism. The space includes 3 bedrooms (sleeps up to six) and 2.5 bathrooms stocked with towels, linens, and basic toiletries. With the full couch and inflatable mattress available, plus plenty of floor spaces, we can accommodate as many as 8 guests. There is an upstairs apartment on the 3rd floor.

Kitchen · Family · Parking

Modern 1BR Walking Distance to Downtown Wooster

Welcome to our cozy Airbnb just walking distance to the heart of Downtown Wooster. This charming upstairs unit with one-bedroom layout is perfect for hosting up to 2 guests comfortably with 1 king bed, adjustable bedframe, lights, and USB ports. Dedicated parking spot provides added convenience and peace of mind during your stay. Whether business or pleasure, our Airbnb offers the perfect blend of comfort, convenience, and style for your next getaway. We look forward to hosting you!

Family · Kitchen · Location

Cabin with pond & Fireplace * Hot Tub * King Bed

A quaint, cozy newly remodeled in 2025 cabin on 60 wooded acres perfect for a couples getaway. 8 minutes to a great downtown for shopping unique boutiques, dining, local wineries, breweries and distillery! Enjoy peace & tranquility in natures setting. Cozy up to a massive stone wood burning fireplace both inside and on the screened in porch. The brand new private hot tub boasts natural spring water and is just outside the door from the cabin and overlooks the natural spring ponds.

Kitchen · Family · Check-in

Lovely 2-bedroom loft with indoor fireplace

Welcome! This spacious 2 bedroom 1 bath apartment is located in the heart of Downtown Wooster. Walking distance from restaurants, coffee shops, boutique shopping, minutes from the College of Wooster, a short drive to Amish country and much more! This unique and stylish space will have everything you need for your stay. Whether you are looking for a night away or wanting to stay long term Life on Liberty was designed with you in mind.

Kitchen · Family · Laundry

Downtown Wooster Cottage

Welcome! We are so excited to have you! This stylish place to stay is perfect for your family or with your friends trip. This spacious 3 bedroom 1 and 1/2 bath home has all that you need for a good time. It is located at the heart of down town Wooster. Walking distance to the Collage of Wooster, coffee shops, bakeries, bookstores, shopping, and so many adorable restaurants. A short drive to Amish country and so much more.

Family · Indoor spaces · Sleep quality

Historic hideaway in downtown studio apartment

This urban-styled studio is located in the heart of historic downtown Wooster. You can walk to some of the most popular local restaurants, specialty boutiques, coffee shops, and more. Featuring the original exposed brick, this unique space can accommodate 1-2 guests with one king bed, living area, and fully stocked kitchen. Explore the rooftop access where you can sit and enjoy the scenic views of downtown.

Indoor spaces · Kitchen · Checkout

Wooster private apartment near Amish Country

Enjoy a private 1 bed, 1 bath, full kitchen, private patio, close to downtown Wooster, 1.5 mi from OARDC/Secrest Arboretum, 3.5 mi to College of Wooster, 1 hr drive to CLE airport. Enjoy the heart of Amish Country while saving money being 30 min away from the tourist hub! Family lives on-site (above the airbnb) so some dog and kid noise expected. Plenty of parking for 2 cars. Apt is self-check in.

Family · Indoor spaces · Laundry