Holiday rentals with outdoor seating in Wooster

Sky Ridge-The Dawn/Brand New Cabin/Amish Country

Nestled in the beautiful hills of Amish Country, minutes from downtown Millersburg. The Dawn faces the East, featuring a breathtaking view of the sunrise every morning. Whether you're looking for a peaceful getaway or wanting to explore the many attractions Holmes County has to offer, this is the place for you. Come and experience Sky Ridge Lodging! If golfing is your sport be sure to check out our Hosted Course at Fire Ridge Golf only minutes away. Be sure to mention Sky Ridge for a discount!

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!

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.

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).

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.

CF Ranch & Cattle Co.- Lodge and CrossFit Gym

This beautiful, one of a kind lodge, is located on a 270 acres Texas longhorn ranch. At CF Ranch & Cattle Company, we offer a great experience to stay on a working cattle ranch. Many trails to walk, a large 8-9 person Hot tub , new CrossFit gym, majestic Texas Longhorn to view. The balconies show miles of amazing views and rolling farm land, along side some of our biggest show cattle. We are located 6 miles from shopping, Walmart and movies. 25 miles from Holmes county Amish

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.

Tiny House on Jericho with Hot Tub

Reconnect at this unforgettable escape. Everything you need for a couple's getaway, in a small space! Our tiny house is packed with the necessary amenities and beyond. Relax in the hot tub, enjoy the fire pit (firewood & starter provided), or take a one minute trip to Kidron, where you will find the world-famous Lehman's store. We are also less than 30 minutes from Berlin, Ohio and all the shops and restaurants it has to offer.

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.

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