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Holiday rentals in Winterset

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Top-rated holiday rentals in Winterset

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Guest favourite
A charming log cabin is set against a backdrop of vibrant fall foliage. The cabin features a covered porch with wooden railings and a peaked roof, embraced by a spacious green lawn. The warm wood tones of the cabin provide a welcoming appearance.
Cabin in Fresno
4.94 out of 5 average rating, 243 reviews

Deer Creek Cabin | Sport Court | Hot Tub

Our hi-end cabin offers a beautiful country setting on 4 acres and comes equipped with luxurious bedroom suites! Soak in the hot tub and enjoy the peaceful view from the log cabin deck or sip a fresh cup of coffee on the hickory rocking chairs on the front porch. Our family-friendly space comfortably sleeps 11 guests, and larger groups are welcome! The large lawn is perfect for games, tent camping, and quality time around the campfire. Come experience our cozy space, make your reservation today!

Top guest favourite
The exterior of a rustic cabin is surrounded by lush greenery. The cabin features a wooden facade and a spacious front deck that overlooks a well-maintained lawn, framed by a wooden fence. Tall trees provide natural shade in the background.
Cabin in New Philadelphia
4.94 out of 5 average rating, 200 reviews

Cozy Hollow Cabin with Hot Tub

Relax with the whole family at the Cozy Hollow Cabin. Located in a peaceful area on 2 acres of property near Sugarcreek Ohio. Looking to just stay in for the weekend? Relax in the hot tub and enjoy nature, or head inside to our game room, 3 TVs, and fully functional kitchen. We have 3 Bedrooms and a pullout couch in the common area upstairs. Some attractions nearby are The World's Largest Cuckoo Clock, The Amish Flea Market, and Breitenbach Winery. Enjoy your time away at our peaceful cabin.

Top guest favourite
A modern cabin is featured, surrounded by trees and bathed in golden light from the setting sun. A spacious deck extends from the cabin, providing seating areas, while steps lead down to the gravel path below amidst lush landscaping.
Place to stay in Sugarcreek
4.96 out of 5 average rating, 330 reviews

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!

Top guest favourite
An inviting exterior view of a single-story house is featured, surrounded by autumn foliage. A fire pit, surrounded by log seating, is set on a gravel area, providing a cozy gathering spot. Soft evening light casts a warm glow over the landscape.
Home in Butler
4.98 out of 5 average rating, 132 reviews

Stylish 3BR Near Snow Trails & Mohican!

Tucked away in rural Ohio minutes from Mohican & Snow Trails, this stylish, updates house is your dream getaway! 3 bedrooms and 1 bathroom with fabulous gathering spaces make this home perfect for outdoor lovers to relax and connect between adventures. Use our InstaCamera to see your favorite memories. Catch breathtaking sunsets over the treetops as you enjoy the view from the balcony. Decompress from your busy life and connect at Stay@Mohican! Host occupies the walkout basement apartment

Top guest favourite
A rustic cabin features earthy stonework and large windows, surrounded by lush greenery. Stone steps lead to a patio area adorned with planters. A vibrant red door adds a pop of color, while trees provide a natural backdrop, creating a serene environment.
Home in Fresno
4.98 out of 5 average rating, 142 reviews

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.

Guest favourite
The treehouse structure is elevated, supported by wooden pillars and surrounded by lush greenery. The exterior features a combination of stone and wood, while a wraparound deck provides views of the natural landscape. Large windows allow light to enter the living spaces.
Treehouse in Sugarcreek
4.98 out of 5 average rating, 192 reviews

The Treehouse @Brandywine Grove

Reconnect with nature at this unforgettable treehouse escape. Experience a truly unique stay 22ft in the air spanning across a ravine, amongst large maple trees and a wraparound deck overlooking your private pond. *NO pet policy & No parties at the cabin as this is a quiet neighborhood and this place is intended for relaxation and enjoying nature, Making memories with loved ones! ** Absolutely NO elopements or weddings permitted on the property unless a contract is signed with the owner.

Guest favourite
The exterior of Rosedale Timber Lodge is presented at dusk, featuring a blend of stone and timber framing. Soft lighting highlights the entrance, while expansive grounds and trees are visible in the background against a colorful sky.
Cabin in Salesville
4.89 out of 5 average rating, 160 reviews

Rosedale Timber Lodge

Rosedale Timber Lodge is the perfect quiet retreat. Nestled in the hills of Guernsey County, with no neighbors in sight, you can truly kick back and enjoy nature. Completely restored recently, this lodge is beautifull inside and out with timber framing, a custom kitchen, stone fireplace, fishing pond, volleyball court, wiffleball diamond, and game room in the basement. We also offer 3 full RV hookups! After your stay, you will leave here more relaxed and refreshed than ever!

Top guest favourite
A living room is presented with a green accent wall and features two comfortable black leather sofas facing a wooden coffee table. An antique cabinet and a wall-mounted deer head add character, while softly lit recessed lighting enhances the cozy setting.
Flat in Dundee
4.96 out of 5 average rating, 123 reviews

Peaceful Hills

Looking for a quiet place to come relax in Amish Country? This is the place for you to stay. We are back in the hills of Amish Country where it’s quiet and relaxing. We are 4 miles from Sugarcreek, 5 miles from Walnut Creek and 9 miles from Berlin. Come bring the whole family to this great place with lots of room, 2 Bedrooms with Queen beds, 2 Bathrooms, plus a cot and single mattress available, full kitchen and living room, 1900 SQ FT NO PETS, NO SMOKING, NO DRINKING

Top guest favourite
The A-frame structure is surrounded by lush greenery, featuring large glass panels that reflect the forest. A warm wooden deck with seating arrangements invites relaxation. Soft exterior lighting enhances the space, creating a welcoming ambiance as evening approaches.
Cabin in Walhonding
4.98 out of 5 average rating, 482 reviews

Black Gables Aframe | Wooded Retreat with Hot Tub

We look forward to welcoming you to the secluded beauty of our space, designed and built by my husband 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.

Top guest favourite
A rustic cabin is nestled among lush greenery, featuring a wood exterior with large windows. A hot tub is located on the deck, complementing the peaceful country setting. The gentle slope of the lawn enhances the serene atmosphere.
Cabin in Newcomerstown
4.99 out of 5 average rating, 170 reviews

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.

Guest favourite
Cabin in Byesville
4.93 out of 5 average rating, 342 reviews

High Tech Cabin in the Hills of Guernsey County

Come and visit our clean and cozy one bedroom cabin in the wooded hills of Guernsey county Ohio and relax on the spacious deck and listen to the sounds of nature, take a trail walk on the 19 acre property, or stay inside and ask Alexa to play your favorite tunes or stream a blockbuster movie on the 65" 4k UHD TV with 7.2.4 Dolby Atmos surround sound, the choice is yours.

Top guest favourite
An open-concept studio space includes a fully equipped kitchen with wooden cabinetry and a cozy living area. A gray couch and a light armchair are arranged around a decorative rug. Natural light enters through two small windows, complemented by neutral wall colors and exposed wooden beams.
Guest house in Cambridge
4.95 out of 5 average rating, 463 reviews

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.

Popular amenities for Winterset holiday rentals

  1. Airbnb
  2. United States
  3. Ohio
  4. Guernsey County
  5. Winterset