Holiday rentals with outdoor seating in Wooster

Cozy getaway w/ hot tub + patio in Amish Co!

The Benton Guest Suite features a beautiful private patio with a hot tub and gas fire pit, 1 bedroom, 1 bathroom, and a living area with a sofa bed and coffee/tea bar. No checkout to-do list! Just stay & relax. We are a 10 min. drive from Mt Hope, Millersburg, and Berlin. We share our drive with an Amish family farm and because this is our family home, you may occasionally hear the kids playing or tractors driving by. We occupy mostly the top floor but always value your privacy and quiet

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.

Tandem Trails Guestroom- Charming Century home

Tandem Trails is now open to guests year round with even more amenities. This is now a completely private space available for up to 7 days at a time. The home now offers a TV/sitting room that can be converted to a second bedroom with a sleeper ottoman and a futon-type couch. This makes it more accessible to groups such as cyclists traveling together, wedding guests, or a small family. Tandem Trails will only book one group/family at a time. The hosts have moved 3 properties away.

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 Modern Apartment

Urban-vintage uptown apartment, fully furnished & located in an attractive & accessible section of Massillon, is ready for your visit. Updated & modern, this space has everything you will need for a comfortable stay. This one bedroom apartment comes with a new queen mattress & a twin sized day bed in the living room area. The living room is open to the kitchen & has a couch, two chairs, ottoman/coffee table, & sofa table. The neighborhood is only short distance from downtown.

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.