Holiday rentals with outdoor seating in Wooster

Scandi Cabin•Hot Tub•4 Electric Fireplaces•

Built in ‘22! In the woods of Strasburg The White Oak Cabin: •2 bed •2 bath •Fully stocked kitchen 🧑‍🍳 •4 Electric Fireplaces 🔥 •Living room with 50”TV 📺 •Climate control in each room ❄️ •Step ladder to loft 🪜 In the loft: •Dedicated workspace 💻 •1 Huge Sectional-room for 2 😴 •50” TV •Fireplace 30 minutes > Pro Football Hall of Fame 15 minutes > Sugarcreek (Amish Country) 20 minutes > 6 wineries On the Outside •Hot Tub •Fire Pit •Gas Grill •Level 2 EV charger •Adirondack Chairs

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.

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

Black Gables Aframe | Hot Tub and Pellet Stove

We look forward to welcoming you to the secluded beauty of our space, designed and built by Kenny on our 20 acres of wooded property in the rolling hills of Central Ohio. A floor-to-ceiling glass front provides you with a view of fields green in summertime and ripe with goldenrod in the fall, four outdoor deck spaces invite you to relax in the beauty of nature, and a second story loft suite with a soaking tub are ready to provide you with rest and refreshment.

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.

Farm Lane Guest House

Nestled only one mile from the square in Berlin, this quaint tiny house offers a relaxing retreat for your visit to Amish Country. This charming abode features two cozy bedrooms, a pristine bathroom, a welcoming living area, and a fully-equipped kitchen. Guests can unwind and enjoy a slower pace of life. Whether you’re sipping coffee to start your day or exploring nearby shops and attractions, our tiny house is the perfect place for a memorable retreat.

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.

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.