House holiday rentals in Wooster

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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, 191 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, 144 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, 108 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
A master bedroom is presented with a queen bed covered in a light-colored quilt. A ceiling fan provides ventilation, and a desk with a chair is positioned nearby. A television is mounted on the wall, and light streams in through sheer curtains on a window.
Home in Massillon
4.98 out of 5 average rating, 101 reviews

Towpath Tranquility! Fenced Yrd,Extended Stay,W&D!

Bring the whole family to this great place with lots of room for fun! Located a few yards from the Towpath Trl, 2 min to Hwy access, easy walk to downtown w/ shopping, dining and entertainment! Full Fenced back yard, sun room = game night, gathering with family & friends. Perfect for families, pets, extended stay & business travel! Guests love to visit Pro Football Hall of Fame, Clays Resort Jellystone Park , Cherry Rd Winery, Historic Spring Hill! Don't miss it! READ all info prior to booking.

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, 149 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 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, 200 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 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, 273 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 minutes from Canton and from Amish country. It is adjacent to Peacock Ridge, a barn wedding site and near to the Sippo Valley trail.

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, 200 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
The exterior of the spacious home features a welcoming front porch with multiple seating options, framed by greenery. The facade is adorned with warm lighting and classic shutters, adding character to the structure. A central entrance leads into the inviting interior.
Home in Millersburg
4.94 out of 5 average rating, 213 reviews

Spacious 2 BR home, just minutes from Berlin, OH.

This spacious home is located in the heart of Ohio's Amish country, on a beautiful township road just 3 miles from downtown Berlin! This 1,800 sq ft space features TWO BEDROOMS and a large front porch. The living area is spacious! NEW ADDITIONS: All New Flooring in 2021, a ping pong table and a brand new 75” smart tv! A beautiful, full kitchen awaits you with a full range, microwave, refrigerator, etc. Coffee and snacks are supplied. Our guests have access to free wifi.

Top guest favourite
An inviting porch area is illuminated by warm overhead lights, highlighting the stone accents of the entrance. Comfortable chairs are arranged along the front, with a small potted plant nearby. The structure features a welcoming door and large windows that enhance the exterior's charm.
Home in Dundee
4.99 out of 5 average rating, 489 reviews

Walnut Valley Farm guesthouse

Nearby the Dundee Falls (3 miles) Central Amish County Location, 9 miles to Berlin, 6 miles to Sugarcreek or Walnut Creek. Enjoy your morning coffee (or tea!:) looking out over the rolling farmland of Ohio’s glorious Amish Country. Known for its peaceful landscape and peaceful people. This is the perfect place to come and leave the cares of the world behind.

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, 180 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 house 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 £59 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!

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