House holiday rentals in Wooster

4.99 out of 5 average rating, 157 reviews

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

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.

LocationValueDecor

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.

4.98 out of 5 average rating, 343 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

FamilyLocationBackyard

4.98 out of 5 average rating, 115 reviews

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

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.

FamilyValueWi-Fi

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.

4.97 out of 5 average rating, 107 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!

FamilyValueTV

4.97 out of 5 average rating, 178 reviews

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

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.

FamilyValueAccuracy

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.

4.97 out of 5 average rating, 219 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.

FamilyValueNearby

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.

4.96 out of 5 average rating, 217 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.

LocationValueWi-Fi

4.88 out of 5 average rating, 105 reviews

Modern 1BR Walking Distance to Downtown Wooster

Welcome to our cozy Airbnb just walking distance to the heart of Downtown Wooster. This charming upstairs unit with one-bedroom layout is perfect for hosting up to 2 guests comfortably with 1 king bed, adjustable bedframe, lights, and USB ports. Dedicated parking spot provides added convenience and peace of mind during your stay. Whether business or pleasure, our Airbnb offers the perfect blend of comfort, convenience, and style for your next getaway. We look forward to hosting you!

LocationFamilyWalkability

5.0 out of 5 average rating, 110 reviews

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

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.

LocationFamilyKitchen

4.98 out of 5 average rating, 190 reviews

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

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.

ValueFamilyAccess

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.

4.97 out of 5 average rating, 115 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.

LocationValueIndoor spaces

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.

4.99 out of 5 average rating, 517 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.

LocationValueOutdoor spaces

Popular amenities for Wooster house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.8 out of 5 average rating, 120 reviews

The exterior of the resort home features a combination of brick and large windows, surrounded by lush greenery. A spacious driveway leads to the entrance, flanked by trees and landscaped plants, creating a serene setting within the wooded surroundings.

Home in Congress

Hidden Ariel Resort

LocationFamilyBarbecue

4.97 out of 5 average rating, 207 reviews

The exterior of Liberty Hill Lodge is presented from an aerial perspective, highlighting the spacious layout and landscaped grounds. A fenced-in heated pool is seen in the backyard, surrounded by lounge chairs and shaded seating areas. Lush greenery offers a peaceful and inviting outdoor environment.

Home in New Philadelphia

Liberty Hill Lodge, Hot Tub & Pool

FamilyValueLaundry

4.79 out of 5 average rating, 109 reviews

A cozy living area is presented, featuring leather sofas arranged around a wooden coffee table. Natural light floods in through sliding doors, providing a view of the outdoor space. A pair of armchairs and decorative accents enhance the inviting environment.

Home in Mansfield

The Banyon Ranch!

FamilyValueCleanliness

5.0 out of 5 average rating, 23 reviews

Home away from home.

ValueFamilyCleanliness

4.93 out of 5 average rating, 45 reviews

The outdoor area features a well-maintained pool surrounded by lounge chairs and sunshades. Decorative palm trees add a tropical touch. A spacious two-story house is visible in the background, and a covered patio is accessible from the pool area, providing additional seating and shaded space.

Home in Millersburg

Berlin Pool House

FamilyLocationIndoor spaces

A newly remodeled home is depicted with a clear blue pool in the foreground. The structure features multiple windows and a small patio area, surrounded by greenery. The inviting pool reflects the house and the surrounding trees, emphasizing a peaceful outdoor setting.

4.95 out of 5 average rating, 59 reviews

Private Pool Retreat in Amish Country

LocationFamilyOutdoor spaces

5.0 out of 5 average rating, 95 reviews

A modern kitchen features warm wooden countertops and stylish metal bar stools. Cabinets hold neatly arranged dishware, while a patterned backsplash adds visual interest. Bright pendant lights illuminate the space, and a bottle of wine is set alongside two glasses, creating a welcoming setting.

Home in Sugarcreek

Amish Country Farmhouse Sugarcreek in Countryside

ValueFamilyCondition

4.97 out of 5 average rating, 35 reviews

Country Comfort w/ Pool & Hot Tub-Family & Groups

FamilyLocationKitchen

Weekly house rentals

4.97 out of 5 average rating, 120 reviews

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

Lovely Private Home w/ Cozy Farmhouse Charm

FamilyLocationHiking

4.96 out of 5 average rating, 288 reviews

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

Pleasant View Farmhouse and Pickleball Court

LocationValueBiking

4.87 out of 5 average rating, 194 reviews

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

Whispering Pines - Secluded / Spacious Yard

ValueLocationBiking

4.94 out of 5 average rating, 106 reviews

A spacious living area features a light-colored sectional sofa and a matching armchair. Natural light enters through large windows adorned with simple curtains, highlighting the warm wooden flooring. A small round table sits beside the sofa, accompanied by a decorative plant and a minimalist lamp.

Home in Sugarcreek

Copper Hill Home in Walnut Creek

FamilyValueLaundry

A spacious deck is shown in front of a wooden house, featuring a small round firepit on the grassy lawn. Chairs are positioned on the deck, offering views of the surrounding greenery and hills under a partly cloudy sky.

4.97 out of 5 average rating, 117 reviews

Peaceful Meadows/Outdoordining/Breo Firepit/Grill

FamilyLocationLayout

5.0 out of 5 average rating, 101 reviews

The outdoor living area is illuminated by soft string lights, highlighting the covered patio and comfortable upholstered seating. Lush greenery surrounds the space, with potted plants lining the edges, creating a tranquil environment for evening relaxation.

Home in Loudonville

Hot Tub • Fire Pit • Pool Table • Ping Pong

LocationValueComfort

4.98 out of 5 average rating, 349 reviews

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

Oasis of Carlisle in Amish Country

LocationValueView

A sunlit seating area features two soft, light-colored chairs with metal frames positioned near a small round table. A floor lamp stands beside the chairs, illuminating the space, while light filters through wooden blinds revealing a wintry scene outside.

4.95 out of 5 average rating, 44 reviews

Classic home next to the College of Wooster!

ValueFamilyBathroom

Private house rentals

A spacious home is featured with a combination of stone and siding, set against a wide green lawn. The front porch is supported by elegant columns, and expansive windows allow for ample natural light. A nearby tree line is visible in the background.

4.89 out of 5 average rating, 75 reviews

Beautiful Country Side Mansion

FamilyLocationOutdoor spaces

A spacious bedroom features a four-poster bed with a white quilt and accent pillows. Two side tables with lamps provide soft lighting. Natural light streams through large windows, while a small table and chair set is positioned in the corner of the room.

5.0 out of 5 average rating, 25 reviews

Warner Homestead

FamilyLocationCleanliness

5.0 out of 5 average rating, 22 reviews

Oak Cottage

LocationFamilyNearby

The exterior of a two-story home built in 1920 is visible, featuring a light-colored facade with contrasting trim. A welcoming front porch provides seating, while a gravel path leads to the main entrance. Lush greenery and a manicured lawn complement the relaxed atmosphere.

4.83 out of 5 average rating, 70 reviews

Spink Street Extended Stay Craftsman Home.

LocationFamilyAccuracy

5.0 out of 5 average rating, 28 reviews

Home in Orrville

Cozy Cottage Retreat- Guest House

FamilyLocationHospitality

4.86 out of 5 average rating, 14 reviews

Historic & Luxurious Farmhouse on 19 Acres

FamilyLocationNearby

Superhost

A charming outdoor space is seen, featuring a cozy patio area with several black chairs arranged around a gas grill. The modern design showcases a striking house with large windows, framed by wooden fencing and string lights above, set amidst green foliage.

Home in Apple Creek

4.89 out of 5 average rating, 64 reviews

Edinburgh Escape | Hot Tub, Sauna + Fire Pit

LocationValueComfort

The exterior of the home is showcased, featuring a welcoming entrance with a covered porch. Lush green grass surrounds the structure, accompanied by vibrant shrubs and trees. An American flag hangs, adding a traditional touch to the inviting facade.