House holiday rentals in Wooster

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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 $102 SGD 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Wooster holiday rentals include wifi 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!

Top-rated house rentals in Wooster

Guests agree: these houses are highly rated for location, cleanliness and more.

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Top guest favourite
A two-story house features a front porch adorned with white rocking chairs and surrounded by greenery. A covered roof extends over the entrance, while a large tree casts shade on the lawn, which is well-kept and leads up to a paved sidewalk.
Home in Dalton
4.96 out of 5 average rating, 194 reviews

The Blacksmith House of Kidron

Our house is conveniently located in heart of Kidron, just a 2 minute walk to the square. We offer the convenience of small town living with a country feel. Lehman's Hardware (voted best destination in Ohio's Amish country) is a short 2 minute walk. Kidron community park, Kidron Town & Country store, Kidron pizza & Ice cream as well as MCC thrift shop are a short walk away! As well as Berlin, Canton (home of the Football Hall of Fame) , Wooster & Sugarcreek are just a short 20-30 minute drive.

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, 148 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
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, 324 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, 277 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, 159 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, 343 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, 205 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.

Guest favourite
An outdoor patio space features a wooden deck with a dining table and chairs, alongside a flower pot. A four-burner grill is positioned in the background, with trees visible beyond the deck, providing a sense of seclusion.
Home in Millersburg
4.89 out of 5 average rating, 288 reviews

[Six-Container Home]With panoramic views + Hot Tub

Escape from the chaos in our modern 1,600 square foot container house! A true bucket list experience! Nestled far enough in the trees to give you privacy, yet only minutes from downtown Millersburg. Get some groceries at Rhodes (2 minute drive) or a cup of joe from Jitters Coffee House (5 minute drive). Spend the day shopping & exploring Amish Country, and come back to unwind in this unique - The homeowners live beside the house and are available if needed

Top guest favourite
The historic log home is set amidst lush greenery, surrounded by trees and hosta gardens. The front features a stone path leading to a welcoming porch, with flower boxes lining the windows. A gravel drive provides access to the tranquil wooded setting.
Home in Jeromesville
5 out of 5 average rating, 101 reviews

Mohicanville Hideaway

Enjoy a tranquil getaway at this cozy and historic 1836 log home in the woods. During your stay, you will be greeted with a tasteful mix of antique features, Amish craftsmanship, and comfort. Start your day with a cup of coffee or tea on the screened porch in the company of the deer who often visit. End your day relaxing in the hot tub or unwinding next to a wood-burning fire (inside or out) before luxuriating in bamboo sheets for a restful night's sleep.

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.

Popular amenities for house rentals in Wooster

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Avg. price$188 SGD$203 SGD$204 SGD$178 SGD$183 SGD$180 SGD$206 SGD$198 SGD$195 SGD$198 SGD$198 SGD$198 SGD
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