Vacation rentals with outdoor seating in Wooster

Peaceful Country Home in Holmes Co. OH (sleeps 8+)

Experience the warmth and charm of this cozy country home nestled in the heart of Amish Country. Surrounded by peaceful serenity, it's the perfect place to slow down and savor the simple joys of life. Unwind at the new "Binzebo" with a firepit, or relax on the deck overlooking our dairy farm and stunning sunsets. Just a short drive away, enjoy the natural beauty of Mohican State Park for hiking adventures, or the nearby Amish shops, delicious dining, and local attractions waiting to be explored.

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!

The Haven / Scenic Aframe cabin

The Haven is just that - a place of rest. Keep it simple at this peaceful and centrally-located place. The cabin is nestled in a wooded area with a pond view and rolling hills. In the heart of beautiful Amish country we are just minutes away from popular attractions. The living area includes a full kitchen, washer and dryer, and comfortable furniture to enjoy a smart tv and fireplace. A King bed and full bath on the main floor. The loft has a queen bed. We welcome you to come stay with us!

Whispering Pines Retreat by Private lake/ Villa #2

Whispering Pines Retreat #2 Kick back and relax in this calm, stylish space. Only 1/2 mile off SR 30, Overlooking a large pond with a swim area and beach. A massive 2 person shower and a hot tub are only a few things you will love about this retreat. This listing is for Villa and lake #2 and is what you are seeing in the photos. There is another Villa and Lake #1 on the same property. If you want to book both on the same days you can do so by going to my profile and finding #1 there.

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.

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.

Cozy Home near College of Wooster

Cozy 3 bedroom house near College of Wooster. Five minute walk to Timken Gymnasium or Freedlander Theater and a 10-15 minute walk to downtown restaurants, coffee shops and boutiques. Residential neighborhood near campus. All the amenities you will need for a comfortable and affordable stay. Relax in the living room, enjoy one of three queen size beds along with a fully equipped kitchen and dining area. Also feel free to park in our attached one car garage.

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.

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.

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.

Amish Country Silo

Experience a one-of-a-kind romantic retreat in a charming grain bin with a modern farmhouse interior. This unique escape offers every amenity to ensure an unforgettable getaway. Gaze out the windows to take in the breathtaking views of the picturesque farmland. You're just 30 minutes from the heart of Amish Country, complete with the best shopping and restaurants!

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.