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 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, 138 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 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, 102 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
The exterior of a light blue single-story house is depicted, featuring a covered porch with two chairs and a small table. A white fence with a decorative star complements the yard, which is dotted with flowers and vibrant green grass.
Home in Massillon
4.97 out of 5 average rating, 209 reviews

Family Comfort!Trails,W/D,Pets,Extend Stay&Coffee!

Book with someone you can trust! Proud to meet Massillon City requirements - inspected and certified Airbnb! Cozy atmosphere to gather for quality time with friends & family. Cooking essentials provided for a home made meal! Walk to gas station, restaurant & Downtown! 2 min to Hwy! Maximum convenience! Large back yard for kids & pets to play. Small, fenced lounge area with grill off of kitchen. Perfect for families, business & extended stays! Review all listing info before booking. Thx!

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, 129 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
4.96 out of 5 average rating, 198 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
The living area is furnished with comfortable leather couches and a wooden coffee table, creating a relaxing space. A large television displays streaming options, while natural light enters through the windows, highlighting decorative plants and wall art.
Home in Highland Square
4.95 out of 5 average rating, 139 reviews

Entire Home Highland Square/CVNP

Enjoy a comfortable experience at this centrally-located home 1 block away from the strip in Highland Square. Central air, 2 bedrooms with brand new queen beds. Large kitchen with dishwasher. Netflix & Prime Video on tv's. Comfortable leather couches, front and back deck, and fire pit. Being 5 minutes from Downtown Akron, 35 minutes from Downtown Cleveland, and 10 minutes from Cuyahoga Valley National Park, there is a lot of nightlife, hiking and biking in the area. All are welcome!

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, 191 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
A cozy firepit area is surrounded by a circular arrangement of stone seating. Softly glowing string lights are hung overhead, illuminating the gravel space. The setting is nestled against a backdrop of trees, providing a serene atmosphere for gatherings.
Home in Loudonville
4.99 out of 5 average rating, 154 reviews

Mystic Cliffs Hideaway

Mystic Cliff offers a beautiful setting for families and friends to get away and make memories. This newly renovated 3 bedroom home is nestled on 7 wooded acres for you to explore. Enjoy the scenic firepit on top a large standing rock formation. And watch the wildlife roam. Even from the front porch. It is conveniently located just a few miles from Mohican State Park. With trails, a river, adventures, places to eat, Landoll's Castle and more.

Guest favourite
Home in Akron
4.83 out of 5 average rating, 180 reviews

Spacious 2 Bedroom House

Spacious two bedroom house in a quiet neighborhood away from city noise and only 7 minutes away from Downtown Akron where many go for dining and experiences. There is plenty of parking in the driveway. We offer many amenities and the property is fully secured. Beautiful, tranquil fish pond outside to admire on warm summer days in Ohio. There will be someone available at all times to assist you if you should need anything.

Top guest favourite
Home in Strasburg
4.98 out of 5 average rating, 347 reviews

Scandi Cabin•Hot Tub• 4 Electric Fireplaces•

The White Oak Cabin: Built in ‘22 •2 bed •2 bath •Hot Tub •Fully stocked kitchen ‍ •4 Electric Fireplaces •Living room - 50”TV •Climate control in each room ❄️ •Step ladder to loft In the loft: •Workspace •1 Huge Sectional-room for 2 •50” TV •Fireplace 30 minutes > Pro Football Hall of Fame 15 minutes > Sugarcreek (Amish Country) 20 minutes > 6 wineries 60min > Cuyahoga Valley National Park

Top guest favourite
The modern kitchen features sleek black cabinetry and a spacious countertop. Essential appliances include a refrigerator, oven, microwave, and toaster. Open shelving displays glassware and plates, while under-cabinet lighting enhances visibility. A window allows natural light to enter, illuminating the space.
Home in Ashland
4.99 out of 5 average rating, 149 reviews

Cozy Ashland Cottage - Close to Downtown

Welcome to our cozy Ashland cottage! The home is located just 3 minutes from downtown, 4 minutes to Ashland University, and just over 10 minutes to I71. The home is fully stocked with all of the essentials you will need for a great stay in our little town!

Guest favourite
A white, two-story house with a sloped roof is set in a spacious, grassy area. Flower beds and a winding path lead to the entrance. Multiple windows provide natural light, and a small outdoor seating area is visible on the side of the property.
Home in Apple Creek
4.84 out of 5 average rating, 256 reviews

A Dawdi Haus in Amish Country Ohio!

A modern 4 bedroom Dawdi Haus (Amish grandparents home) in the heart of Amish Country. Close to everything! Why rent a room when you can rent a fully furnished home that can hold 12+ people. Beautiful 2 acre property with a barn for your animals!

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 £52 per night before taxes and fees

  • Verified guest reviews

    Over 1,810 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 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

  • 4.9 Average rating

    Wooster stays are highly rated by guests – averaging 4.9 out of 5!

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