Holiday rentals with outdoor seating 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!

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 #1

Whispering Pines Retreat #1 This stylish villa is Located 1/2 mile from 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 of the things you will love about this Retreat. This listing is for Villa and lake #1 and is what you are seeing in the photos. There is another Villa and Lake #2 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 the other listing 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.

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.

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.

Tiny House on Jericho with Hot Tub

Reconnect at this unforgettable escape. Everything you need, 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.