Vacation rentals in Winterset

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!

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!

Romantic private cabin w hot tub in Amish Country

Retreat to the Fresno Escape! A private cabin featuring a year-round hot tub, perfect for relaxation. Tucked among pines and rocks in the heart of Amish country, where the occasional clip-clop of horse and buggies adds charm. Styled like a railroad depot, the artistically furnished home displays intricate stonework, tile and custom stained glass. The kitchen includes appliances and cookware, with the outdoor area offering a propane grill. Complimentary firewood is provided for the firepit.

A-frame at Creekside Dwellings w/Hot Tub

The A-frame at Creekside Dwellings is a small + impactful oasis near beautiful Amish Country! Only 6 miles from Winesburg + 13 miles from Berlin. There are an endless supply of local attractions. The Pro Football Hall of Fame only 30 minutes away, as well! The A-frame is stocked with all the amenities you will need to kick back and relax! Enjoy the steaming hot tub, gas grill, and tree top views. *note on location: the A-frame is visible from the road during the winter months

Cozy 2 Bedroom Cabin with Hot Tub

Relax with the whole family at this peaceful cabin in the country. Surrounded by woods, rolling hills and plenty of wildlife to watch. A pond is a nice walk up the gradual hill behind the cabin. Located in the heart of Three Rivers Wine Trail, there are plenty of wineries to visit, as well as our favorite local brewery, the Wooly Pig. There’s a large hot tub to enjoy on the deck outside that is big enough for 8 people.

Baltic Loft on Main

Built in an 1800's era theater, our loft is filled with unique charm and character! The loft features original exposed brick, tall ceilings, and original hardwood floors. The space is spacious, yet cozy! After remodeling the theater into an apartment, our family called this loft home for over 3 years. It was a special home where our first child took her first steps. Now, we are excited to share our space with you!

The Owl's Perch Treehouse

Special Reconnect and Rekindle Pricing! Escape to The Owl's Perch at Owl Hollow, where the magic comes alive. Cozy up with the ones you love in the comfort of your arboreal abode. The Owl's Perch Treehouse offers a one-of-a-kind luxury escape. Combining rustic charm with refined comfort. Whether you’re seeking a peaceful getaway or a romantic retreat, the Owl's Perch invites you to relax and reconnect.

Amish Country Silo

Experience a one-of-a-kind romantic retreat in a charming grain bin with a modern farmhouse interior. This unique escape offers every amenity to ensure an unforgettable getaway. Gaze out the windows to take in the breathtaking views of the picturesque farmland. You're just 30 minutes from the heart of Amish Country, complete with the best shopping and restaurants!

The Bunker House

This is a cozy studio concrete “bunker” house across the driveway from our residence. the Bunker has a private patio with a hot tub. It is located on an idyllic 35 acre property with two ponds that connects to Salt Fork State Park public land. We are located a few miles from the State Park entrance and Deerassic Park and close to I77 and I70.

Sugar Shack Inn

Newly rebuilt cabin/house located in Edgewater Park, Piedmont lake is our neighbor, hunting is literally 25' away on Muskingum wildlife conservancy land. Lake is walking distance with public boat ramp a .5 mile away. Located in a culdesac which there is only one other cabin on this road, which is also owned by us. Great lake view and quiet.

Magnolia Ridge Geodome•Hot Tub•Hocking Hills

Welcome to our luxury geodome perched on a ridge in the breathtaking Hocking Hills! It's like glamping meets cozy comfort, where you can kick back and soak in nature’s beauty. Perfect for a relaxing escape—don’t forget to take a dip in our fabulous hot tub.

The Acacia

A luxurious A-frame retreat with spacious modern timber frame and soaring ceilings, this thoughtfully-designed getaway has been curated for your comfort. Your escape to the Acacia promises a harmonious blend of modern luxury and timeless tranquility.