House holiday rentals in Wooster

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Top-rated house rentals in Wooster

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Top Guest favourite
A wooden deck area is equipped with a fire pit at its center, surrounded by two adirondack chairs. In the background, a panoramic view of lush green fields and farm structures, including silos and barns, is framed by trees displaying autumn foliage.
Home in Shreve
4.99 out of 5 average rating, 147 reviews

Peaceful Country Home in Holmes Co. OH (sleeps 8+)

Experience the warmth and charm of this cozy country home nestled in the heart of Amish Country. Surrounded by peaceful serenity, it's the perfect place to slow down and savor the simple joys of life. Unwind at the new "Binzebo" with a firepit, or relax on the deck overlooking our dairy farm and stunning sunsets. Just a short drive away, enjoy the natural beauty of Mohican State Park for hiking adventures, or the nearby Amish shops, delicious dining, and local attractions waiting to be explored.

Top Guest favourite
A covered porch with wooden beams provides a shaded area with a swing for three and two chairs. A gravel driveway leads to a neatly landscaped yard featuring green grass, a fire pit, and a shed in the background surrounded by trees.
Home in Millersburg
4.96 out of 5 average rating, 111 reviews

Lovely Private Home w/ Cozy Farmhouse Charm

Come away & enjoy a peaceful, refreshing stay at Vivian’s Serenity Guest House. Nestled in among the rolling hills of Amish Country, cozy up in the inviting house & explore local attractions. Only 1.5 miles from Rails to Trails biking trail, moments to historic downtown Millersburg, 10 minutes to Berlin shopping and great food! 1 mile to the Holmes County Fair Grounds. Whether you’re ready to shop unique boutiques or relax, Serenity House offers seclusion & proximity to all Amish country offers!

Top Guest favourite
An open-concept living space features a well-equipped kitchen with a central island and seating for four. A dining area with white chairs and a round table is visible, alongside a cozy sitting area highlighted by a rug. Decorative lighting fixtures enhance the inviting atmosphere.
Home in Dundee
4.98 out of 5 average rating, 323 reviews

Woodstone Cottage in the Heart of Amish Country

This quaint cottage is nestled in the rolling hills of scenic Amish Country. It's located within a mile of the historical town of Winesburg and 5 miles from Berlin and Walnut Creek. You can explore lots of Coffee Shops, Restaurants, Antique Malls and unique Boutique Shops. You will also find Breitenbach Wine Cellars in Sugarcreek and your kids will love to visit The Farm in Walnut Creek. You will also find lots of spots for hiking. At the Dundee Falls and the Wilderness center located in Wilmont

Top Guest favourite
A large two-story house is depicted with a yellow exterior, featuring a welcoming porch supported by white columns. Snow rests on the roof and the surrounding branches, while symmetrical windows allow natural light to illuminate the interior. The overall structure reflects classic architectural design.
Home in North Lawrence
4.96 out of 5 average rating, 275 reviews

Pleasant View Farmhouse and Pickleball Court

Situated on 80 acres of farm land, this large home is an ideal setting to relax and connect with family and friends! Built in 1904, the house has been restored to much of its original beauty. Aptly named, the setting provides views of picturesque rolling hills and spectacular sunsets. Recently, an outdoor pickleball court was built. Located approx. 20 min. from Canton & from Amish country. It is adjacent to Peacock Ridge, a barn wedding site. It is less than 1/2 mi to the Sippo Valley trail.

Top Guest favourite
A cozy living area features a brown leather sofa and a light-colored armchair, positioned near a side table with a floral arrangement. A patterned wall adds color, and soft lighting is provided by two table lamps. Green drapes frame the windows.
Home in Wooster
4.97 out of 5 average rating, 103 reviews

TheLegacyHouse: Historical Suite Close to Downtown

Welcome to The Legacy House Wooster! This is a charming Victorian home within two blocks from the wonderful downtown attractions, shops and upscale dining. Our grandparents' love for people and hospitality inspired us to create a warm and inviting home where we could share their legacy and traditions with others while restoring their historic home back to it's former beauty. Experience all the amazing opportunities Wooster has to offer while enjoying a unique, comfortable home to relax in!

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, 157 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.

Top Guest favourite
A two-story home is featured, showcasing a modern exterior with dark siding and a light brick foundation. A manicured lawn with decorative shrubs is visible in front. Tall trees provide shade, and a paved driveway leads to the garage, inviting a sense of tranquility.
Home in Millersburg
4.98 out of 5 average rating, 341 reviews

Oasis of Carlisle in Amish Country

Relax & unwind in our fully furnished and completely renovated home. Designed with your relaxation in mind! Located in Walnut Creek, OH in the heart of Amish country. This is a great location in a quiet neighborhood! Enjoy a peaceful evening on the back deck with a glass of wine and feel the stress fade away. Or let the birds and the squirrels entertain you! We are also within walking distance to restaurants and shopping. Just a 5 minute drive to Berlin for more shopping and exploring!

Top Guest favourite
A charming front porch is adorned with climbing greenery and seasonal flowers, creating a welcoming exterior. An American flag is displayed, adding a touch of tradition. The house features light-colored siding and a green roof, complementing the natural surroundings.
Home in Wooster
4.97 out of 5 average rating, 205 reviews

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.

Top Guest favourite
A cozy seating area is visible through a set of double doors, featuring two armchairs with light-colored cushions. A small table with a lamp stands between the chairs, and large windows overlook a green outdoor space, allowing natural light to fill the room.
Home in Wooster
4.96 out of 5 average rating, 203 reviews

Bonnie Jane House

The Bonnie Jane House is a family friendly space on a quiet, tree-lined street, within sight of the College of Wooster and minutes from downtown. Perfect for college, business, and local tourism. The space includes 3 bedrooms (sleeps up to six) and 2.5 bathrooms stocked with towels, linens, and basic toiletries. With the full couch and inflatable mattress available, plus plenty of floor spaces, we can accommodate as many as 8 guests. There is an upstairs apartment on the 3rd floor.

Top Guest favourite
An elegantly designed kitchen features light grey cabinetry and a wooden countertop, complemented by a contemporary stove and ventilation hood. Natural light floods in through a window above the sink, while stylish pendant lighting adds a modern touch. Open shelving displays kitchenware and decorative items.
Home in Wooster
4.96 out of 5 average rating, 104 reviews

Downtown Wooster Cottage

Welcome! We are so excited to have you! This stylish place to stay is perfect for your family or with your friends trip. This spacious 3 bedroom 1 and 1/2 bath home has all that you need for a good time. It is located at the heart of down town Wooster. Walking distance to the Collage of Wooster, coffee shops, bakeries, bookstores, shopping, and so many adorable restaurants. A short drive to Amish country and so much more.

Top Guest favourite
Home in Beach City
4.91 out of 5 average rating, 183 reviews

Serenity Guesthouse | Peaceful ,Country, Hot Tub

We are located in the heart of Amish country. Only few minutes from Dundee falls where you can go hiking ect. 15 minutes from Berlin and or Walnut Creek. If you are looking for a clean relaxing place to stay , look no further:) . We have a big backyard to enjoy. You can see the animals in the pasture from the patio. No pets, no alcoholic parties .

Guest favourite
A kitchen scene features a person stirring a pot on the stove, with additional pots on the counter and various utensils neatly arranged. The countertop showcases a collection of bowls, and cabinets in the background provide ample storage space.
Home in Holmesville
4.87 out of 5 average rating, 183 reviews

Whispering Pines - Secluded / Spacious Yard

This is a secluded country retreat with a spacious yard. Birds, beef cattle, growing corn and hay are some of the things you may see. Nothing beats the sweet aroma of freshly cut hay on a quiet summer evening. The fire ring has a supply of seasoned wood nearby. Light it for relaxing around a cozy campfire.

Popular amenities for Wooster house rentals

When is the best time to visit Wooster?

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Avg. price$252 NZD$272 NZD$274 NZD$238 NZD$245 NZD$242 NZD$276 NZD$265 NZD$262 NZD$265 NZD$265 NZD$265 NZD
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Quick stats about house rentals in Wooster

  • Total holiday rentals

    Explore 30 holiday rentals in Wooster

  • Nightly prices starting at

    Wooster holiday rentals start at $137 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,960 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Wooster holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Wooster rentals

  • 5 Average rating

    Wooster stays are highly rated by guests—averaging 5 out of 5!

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