Holiday houses 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!

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.

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.

Glenmont Bike&Hike Hostel

This Airbnb was created for bikers riding on the OTET. This is above a detached garage at zip code 44628. This one open room with a private bathroom includes towels (toilet, shower, and sink). There is a double bed with linens, tv, wifi, mini-kitchen with microwave, sink, and refrigerator. The stove is not working now. The Airbnb is located a few minutes from the OTET/Glenmont Trailhead. Note: NO PETS or children under age 12 allowed. No smoking or vaping allowed in Airbnb.

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.

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.

Esther's Amish Country Apartment

Esther's Amish Country Apartment is spacious (960 sq. ft. of living space) located on a beautiful quiet 2 acre property. It has a full kitchen, roomy living room area to relax, queen size bed and walk-in shower; additionally, Armstrong Cable with access Netflix, Prime, Apple TV and excellent WiFi for your entertainment We are an easy 15-20 drive to tourist attractions in the area. *** Read "Other things to note" below for details.

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.

Peaceful 2-BR Apartment in the Heart of Smithville

Quiet 2-BR apartment located on the first floor in the heart of Smithville, Ohio. About a 10 min drive to Wooster. The apartment sits in front of a park which has access to hiking paths, baseball, and soccer fields. Local restaurants and stores are walking distance. Space includes 2 Queen Beds Amenities include Wifi, Free parking for 1 vehicle, Washer/Dryer, Full Kitchen, Covered Front Porch and many more.

Private, spacious 1 bedroom apt 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.

Unique Home in Holmesville/ Holmes County

●20 minutes from Wooster, Millersburg, Berlin, Loudenville, and Mt Hope, and within a short drive to Mohican State Park. ●Firepit and chairs on the back patio ●Built in 2022 with contemporary styling and unique touches throughout. ●Set in the small town of Holmesville with a pizza shop and Blue Moon Bistro close by. ●Quality whole bean coffee provided

Historic Victorian Apt in Downtown Wooster Unit 2

Step back into the 1800s in this charming brick Pioneer House in Historic Downtown Wooster. Enjoy the spacious 1,500-sq-ft first-floor apartment that blends vintage elegance with modern comfort—just one block from local eateries, boutiques, and historic sites. Note: daytime construction across the street may create some noise.