Vacation rentals with outdoor seating in Wooster

Tandem Trails Guestroom- Charming Century home

Tandem Trails is a century home in the small but thriving town of Canal Fulton. This private home offers 2 sleeping rooms, the second also transitioning to a sitting/TV room for relaxation. Tandem Trails is only booked to one group/family at a time. Tandem Trails ALSO OFFERS a transit service to booked TT guests detained on the trail due to weather or accident. We will also pick guests up from Cleveland or AKC Airports if scheduled. This service is for fee. (Our home offers a kitchenette only.)

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.

Historic Downtown Wooster Victorian Apartment #2

Step back in time to the 1800s in this charming brick Pioneer House in Historic Downtown Wooster. Enjoy the entire first-floor apartment (approx. 1500 sqft), blending vintage elegance with modern comfort. All while being just a block from local eateries, boutique shopping, and historic sites. *Please note there's construction taking place across the street during daytime hours, which may result in some construction noise during your stay.*

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.

Spacious 2 Bedroom House

Spacious two bedroom house in a quiet neighborhood away from city noise and only 7 minutes away from Downtown Akron where many go for dining and experiences. There is plenty of parking in the driveway. We offer many amenities and the property is fully secured. Beautiful, tranquil fish pond outside to admire on warm summer days in Ohio. There will be someone available at all times to assist you if you should need anything.

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.

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.

Private, spacious 1 bedroom apt 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