Vacation rentals in Orrville

Pleasant View Farmhouse and Pickleball Court

Situated on 80 acres of farm land, this large home is an ideal setting to relax and connect with family and friends! Built in 1904, the house has been restored to much of its original beauty. Aptly named, the setting provides views of picturesque rolling hills and spectacular sunsets. Recently, an outdoor pickleball court was built. Located approx. 20 min. from Canton & from Amish country. It is adjacent to Peacock Ridge, a barn wedding site. It is less than 1/2 mi to the Sippo Valley trail.

Uphill Lodge Luxury Log Cabin, Amish Country, OH

Drive back the 1/2 mile lane to one of the most unique luxury log homes in the country. Uphill lodge was constructed from Yellowstone National Park timbers, salvaged from the infamous 1988 Great Fire. Enjoy the new hottub, 80+windows with spectacular views, massive Arizona Quartz Stone fireplace, private walking trails on our 12 acres, large sledding hill, huge master suite, large gameroom in the basement, and outdoor firepit. Near Amish country shopping/dining/orchards and golf. See you soon!

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!

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.

Elegant Boho apartment in downtown Orrville

Retreat to the harbor. We created this space with you in mind and are always updating and adding to it for your comfort. When we travel, we seek Airbnb, a unique spot that allows us to relax and enjoy the moments. So when we bought this apartment, we knew from the start it needed to be for guests, offering a place of comfort and rest. We renovated the bathroom most recently, and we continue to enhance it to make it great for you. Located right in downtown Orrville, this is ideal for stay!

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.

AZ Longhorns Cabin, a romantic getaway!

Romantic getaway log cabin in the country. Private log cabin with full kitchen and large bathroom and large shower. This cabin was built summer 2016 and we are continuing to landscape and make it a great place to have a romantic getaway or a place to relax and get away from the city. Free WiFi, Hot tub that seats 7, Fire pit area and charcoal grill on back patio, are some of the great features we have to offer! NOW OFFERING EBIKE RENTALS SO ASK ME ABOUT THEM IF INTERESTED!

Downtown Brick Loft Above The Exchange Coffee Co

Located in the heart of historic downtown Canal Fulton, this charming brick loft will truly take you back in time. Walk or bike to all the local restaurants and shops around town or grab coffee at The Exchange downstairs. The 13 large windows give a panoramic water view of the canal way and downtown. Every detail in this space has been lovingly created with comfort and inspiration in mind. Relax and enjoy this one of a kind location.

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.

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.

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.

Sycamore Hill

Relax with the whole family at this peaceful place to stay. Cabin sits on 4 acreas of hill and wooded areas. Main guest area has many new updates including new kitchen, new master bath, updated main bath with tankless hot water heater, new floors, lighting, window blinds, and gas fireplace. 4 Bedrooms feature 1 King Size Bed, 2 Queen Size Beds, and 2 twin air mattress