Family-friendly holiday rentals in Wooster

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, 108 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!

Indoor spacesFamilyHeating

A living room featuring a dark leather sofa with several decorative cushions, accompanied by a matching armchair. A coffee table rests on a patterned rug, and a television is positioned on a modern stand. The space is illuminated by natural light filtering through floral-patterned window curtains.

4.94 out of 5 average rating, 259 reviews

Your 2nd Home Away From Home l Prime location

This is a fully furnished apartment that has all the amenities of home. It is an updated apartment in an older home, but thoughtful touches and attention have been taken to make this feel very comfortable and relaxing. You'll be pleasantly surprised with the atmosphere and the space that you'll have while staying here. The apartment is conveniently located within a couple short blocks of the college, and just a short distance to the wonderful downtown Wooster with plenty of shops and dining.

FamilyKitchenLaundry

The exterior of a cozy apartment is illuminated at dusk, highlighting a welcoming entrance with steps and a covered porch. The soft glow of outdoor lighting enhances the wooden facade and surrounding greenery.

4.87 out of 5 average rating, 172 reviews

Very nice and clean two bedroom apartment on a quiet dead end street. This apartment is in the perfect location to get to anywhere you would like to go within the City in just a few miles!

Make this cozy, spacious apartment your home away from home. Centrally located between Downtown and Uptown Wooster. This home is with in walking distance of West View Manor and the Wooster Country Club. This convenient location gives you easy access to restaurants, shopping centers, the YMCA, the College of Wooster as well as Wooster High School all within 3 miles. It's perfect for one person or bring the whole family. Stop in for a visit and enjoy all the great city of Wooster has to offer!

FamilyIndoor spacesOutdoor spaces

A cozy sleeping area features a spacious bed with a textured blanket and decorative headboard. Two accent chairs sit beside a small side table, complemented by warm lighting from bedside lamps. Soft rugs cover the floor, adding to the welcoming atmosphere.

4.85 out of 5 average rating, 327 reviews

Cozy Abode

The space is a dedicated basement apartment. The space has its own door and lock, but guests will enter through a shared garage entrance. The decor is neat and modern. There is a small kitchenette, giving guests the ability to eat in, or make coffee. The cozy sitting area is a great place to wind down for the evening or enjoy a morning cup of coffee. The apartment is below our living space. While we will do our best to keep noise to a minimum, you will hear kids/footsteps during the day.

KitchenFamilySolo travel

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, 222 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.

KitchenFamilyLaundry

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, 222 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.

Indoor spacesKitchenLocation

4.97 out of 5 average rating, 149 reviews

A charming entrance leads into a cozy cabin space. Light-colored wooden walls enhance the warmth of the room. A comfortable seating area is furnished with a striped blanket and a small heater. A bedroom door and a window, revealing natural light, provide an inviting atmosphere.

Tiny home in Wooster

Welcome to The Cabin at CT Farms!

Tiny-home, located on our 5.5 acre farm in western Wayne county. This brand-new cabin was constructed by local Amish builders. Complete with most amenities you'd find at home, it offers a cozy spot to relax or work. Have a cup of coffee on the porch and listen to the farmland awaken, or catch amazing sunsets in the evening. Located 2 minutes from US Route 30. 1.25 hours from Cleveland/Columbus. 10 minutes from College of Wooster. 30 minutes from Amish Country. (Berlin/Millersburg).

FamilyIndoor spacesAccess

4.88 out of 5 average rating, 107 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!

Indoor spacesKitchenDecor

4.9 out of 5 average rating, 173 reviews

A modern living area features a comfortable brown leather sofa paired with an accent chair beside a sleek, wooden coffee table. A mounted television is above an electric fireplace, providing a cozy focal point. Natural light filters through dual windows adorned with light curtains.

Loft in Wooster

Lovely 2-bedroom loft with indoor fireplace

Welcome! This spacious 2 bedroom 1 bath apartment is located in the heart of Downtown Wooster. Walking distance from restaurants, coffee shops, boutique shopping, minutes from the College of Wooster, a short drive to Amish country and much more! This unique and stylish space will have everything you need for your stay. Whether you are looking for a night away or wanting to stay long term Life on Liberty was designed with you in mind.

KitchenFamilyDecor

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, 118 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.

KitchenIndoor spacesQuiet

4.98 out of 5 average rating, 182 reviews

The open living area features warm wood flooring and exposed brick walls. A spacious seating arrangement includes a dark leather sofa and a tufted coffee table. The kitchen boasts white cabinetry, stainless steel appliances, and a breakfast bar with two stools. Natural light filters through the window.

Loft in Wooster

Historic hideaway in downtown studio apartment

This urban-styled studio is located in the heart of historic downtown Wooster. You can walk to some of the most popular local restaurants, specialty boutiques, coffee shops, and more. Featuring the original exposed brick, this unique space can accommodate 1-2 guests with one king bed, living area, and fully stocked kitchen. Explore the rooftop access where you can sit and enjoy the scenic views of downtown.

FamilyKitchenTV

4.95 out of 5 average rating, 219 reviews

Wooster private apartment near Amish Country

Enjoy a private 1 bed, 1 bath, full kitchen, private patio, close to downtown Wooster, 1.5 mi from OARDC/Secrest Arboretum, 3.5 mi to College of Wooster, 1 hr drive to CLE airport. Enjoy the heart of Amish Country while saving money being 30 min away from the tourist hub! Family lives on-site (above the airbnb) so some dog and kid noise expected. Plenty of parking for 2 cars. Apt is self-check in.

KitchenFamilyCheck-in

Popular amenities for Wooster family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 320 reviews

A well-maintained lawn surrounds the cabin, leading to a serene, spring-fed pond. Two trees provide shade for a hammock, creating a peaceful spot to relax. The greenery reflects the tranquil atmosphere of the property, inviting guests to enjoy the natural setting.

Cottage in Wooster

Cabin with pond & Fireplace * Hot Tub * King Bed

KitchenIndoor spacesSolo travel

5.0 out of 5 average rating, 141 reviews

Farm stay in Burbank

CF Ranch & Cattle Co.- Lodge and CrossFit Gym

KitchenFamilyBathroom

4.94 out of 5 average rating, 416 reviews

The villa is set beside a tranquil pond, featuring a modern design with large windows reflecting the evening lights. Outdoor seating is visible near the water, and a hot tub sits on the patio, inviting relaxation at sunset.

Villa in Jeromesville

Whispering Pines Retreat by Private Lake/ Villa #1

Indoor spacesKitchenCheckout

4.98 out of 5 average rating, 175 reviews

An aerial view of a log cabin is presented beside a tranquil pond, surrounded by lush greenery and gentle hills. The driveway leads up to the cabin, offering a clear view of its rustic design and the serene water reflecting the surrounding landscape.

Cabin in Millersburg

Stillwater Cabin with Hot Tub

Indoor spacesKitchenDecor

4.98 out of 5 average rating, 362 reviews

The exterior of a charming log cabin is displayed, showcasing a dark wooden facade and a metal roof. A welcoming porch with seating is present, accompanied by neatly landscaped greenery and a stone walkway that leads to the entrance.

Cabin in Sterling

AZ Longhorns Cabin, a romantic getaway!

Indoor spacesKitchenGetting around

4.98 out of 5 average rating, 238 reviews

Cabin in Dalton

Uphill Lodge Luxury Log Cabin, Amish Country, OH

FamilyKitchenQuiet

4.92 out of 5 average rating, 210 reviews

A rustic cabin is surrounded by lush greenery, featuring a covered porch decorated with string lights. A stone patio area is equipped with a small round table and black wrought-iron chairs, providing a peaceful outdoor setting for relaxation.

Cabin in Dundee

Rustic Cabin Bridge Gallery

KitchenFamilyPets

5.0 out of 5 average rating, 113 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

FamilyIndoor spacesLayout

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 119 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!

FamilyKitchenAccuracy

4.98 out of 5 average rating, 194 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

KitchenIndoor spacesBarbecue

4.93 out of 5 average rating, 417 reviews

The charming white cottage features a striking red metal roof and a welcoming front porch. Two rockers are positioned on either side of the entrance, while potted plants adorn the porch. The surrounding greenery enhances the peaceful setting of the home.

Cabin in Millersburg

Creekside Cottage

Indoor spacesKitchenCondition

4.86 out of 5 average rating, 105 reviews

An open layout is shown, with a well-equipped kitchen visible in the distance. A seating area features a brown leather couch, and light hardwood flooring extends throughout the space. A bathroom door is seen on the right, alongside a decorative vase and a small dining table.

Apartment in Millersburg

Luxury Studio over Jackson St(Courthouse Studio)

KitchenFamilyValue

Guesthouse in Millersburg

A cozy cabin with a green metal roof is nestled among trees, featuring a welcoming porch with several wooden rocking chairs arranged for relaxation. A grassy area leads up to the entrance, inviting guests to enjoy the tranquil outdoor setting.

Cozy Retreat Tucked in the Heart of Amish Country

FamilyIndoor spacesCondition

4.95 out of 5 average rating, 221 reviews

4.97 out of 5 average rating, 121 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

Indoor spacesFamilyHiking

4.98 out of 5 average rating, 188 reviews

Home in Sugarcreek

Horizon Haven | Family Getaway w/ Big Views

KitchenFamilyAccess

4.92 out of 5 average rating, 592 reviews

A two-story gray house is set back from the street, framed by two mature trees with bright yellow foliage. A covered porch with white railings welcomes visitors. Neatly landscaped grass surrounds the home, with a white picket fence visible in the background.

Home in Medina

Liberty House - Next to Medina Square.

KitchenFamilyAccuracy

Family-friendly home 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

KitchenIndoor spacesCleanliness

4.91 out of 5 average rating, 105 reviews

Farm stay in Canton

House with Pool at Clover Fields Farm

Indoor spacesKitchenLong stay

4.95 out of 5 average rating, 112 reviews

The exterior of the cabin features a spacious patio area with several Adirondack chairs arranged around a fire pit. A covered pergola provides shade, and the stone and wooden structure complements the natural landscape of grass and trees.

Cabin in Millersburg

Family Size Cabin with Kitchen, Fireplace, Hot Tub

Indoor spacesKitchenHospitality

4.98 out of 5 average rating, 460 reviews

An aerial view of a modern tiny home surrounded by greenery. The home's exterior features a sleek, dark facade with wooden accents. A spacious deck is visible, furnished with adirondack chairs, and framed by lush trees, creating a serene outdoor space.

Tiny home in Millersburg

The Scandi - Tiny Home & Sauna in Berlin Ohio

FamilyIndoor spacesBarbecue

4.95 out of 5 average rating, 437 reviews

A bright kitchen area features wooden cabinets and counter space, complemented by modern appliances. A small dining table is present, along with a ceiling fan for ventilation. Light streams in from a window, enhancing the overall warmth of the space. A welcome sign is visible near the entrance.

Home in Millersburg

The Cozy Comfort in the Burg.

FamilyKitchenSleep quality

4.96 out of 5 average rating, 136 reviews

A modern farmhouse with a light-colored exterior is set against a bright sky. The front porch features a railing and steps leading up to the entrance. Small shrubs are planted on either side of the walkway, enhancing the welcoming appearance of the cottage.

Cottage in Millersburg

Cozy 2 Bed Bath Cottage With Private Hot Tub

Indoor spacesFamilyBathroom

4.97 out of 5 average rating, 196 reviews

A charming farmhouse with a white exterior and a distinct gable roof is set against a backdrop of greenery. Two vibrant red chairs are positioned on the front porch, shaded by trees that frame the home, creating a welcoming outdoor space.

Farm stay in Dover

Farmhouse Unique Country Setting

KitchenFamilyBathroom