Family-friendly holiday rentals in Wayne County

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!

4.93 out of 5 average rating, 204 reviews

The living area features a mix of comfortable seating with a gray sofa and an armchair. A wooden coffee table is centered on a light rug, enhancing the space's warmth. Natural light enters through two windows, illuminating the hardwood floor and a nearby potted plant.

Townhouse in Orrville

Elegant Boho apartment in downtown Orrville

Retreat to the harbor. We created this space with you in mind and are always updating and adding to it for your comfort. When we travel, we seek Airbnb, a unique spot that allows us to relax and enjoy the moments. So when we bought this apartment, we knew from the start it needed to be for guests, offering a place of comfort and rest. We renovated the bathroom most recently, and we continue to enhance it to make it great for you. Located right in downtown Orrville, this is ideal for stay!

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.

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.

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).

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

A quaint, cozy newly remodeled in 2025 cabin on 60 wooded acres perfect for a couples getaway. 8 minutes to a great downtown for shopping unique boutiques, dining, local wineries, breweries and distillery! Enjoy peace & tranquility in natures setting. Cozy up to a massive stone wood burning fireplace both inside and on the screened in porch. The brand new private hot tub boasts natural spring water and is just outside the door from the cabin and overlooks the natural spring ponds.

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!

Romantic getaway log cabin in the country. Private log cabin with full kitchen and large bathroom and large shower. This cabin was built summer 2016 and we are continuing to landscape and make it a great place to have a romantic getaway or a place to relax and get away from the city. Free WiFi, Hot tub that seats 7, Fire pit area and charcoal grill on back patio, are some of the great features we have to offer! NOW OFFERING EBIKE RENTALS SO ASK ME ABOUT THEM IF INTERESTED!

4.97 out of 5 average rating, 115 reviews

A secluded cabin is situated among vibrant autumn trees, showcasing an inviting exterior with a large front porch. The gravel driveway leads to the entrance, flanked by colorful foliage and a serene woodland setting.

Cabin in Burbank

Overton Valley: Secluded Cabin on 10 acres

Slip away to a secluded cabin in the woods on 10 acres for a peaceful getaway. The abundance of wildlife and nature's beauty is sure to leave you feeling relaxed and restored. Conveniently located close to Wooster, Ashland, Akron, Canton, and Cleveland. Explore Amish country, visit Cedar Point with the kids, take in a local winery, check out The Pro Football Hall of Fame, or go for a hike on the property. The local attractions are endless!

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.

Holiday home in Smithville

Peaceful 2-BR Apartment in the Heart of Smithville

Quiet 2-BR apartment located on the first floor in the heart of Smithville, Ohio. About a 10 min drive to Wooster. The apartment sits in front of a park which has access to hiking paths, baseball, and soccer fields. Local restaurants and stores are walking distance. Space includes 2 Queen Beds Amenities include Wifi, Free parking for 1 vehicle, Washer/Dryer, Full Kitchen, Covered Front Porch and many more.

4.85 out of 5 average rating, 241 reviews

4.95 out of 5 average rating, 219 reviews

Flat in Wooster

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.

4.96 out of 5 average rating, 112 reviews

An aerial view captures a cabin surrounded by trees adorned in vibrant autumn foliage, showcasing a rich palette of oranges, yellows, and reds. A winding path leads up to the structure, nestled within the serene wooded landscape.

Cabin in Sterling

Sycamore Hill

Relax with the whole family at this peaceful place to stay. Cabin sits on 4 acreas of hill and wooded areas. Main guest area has many new updates including new kitchen, new master bath, updated main bath with tankless hot water heater, new floors, lighting, window blinds, and gas fireplace. 4 Bedrooms feature 1 King Size Bed, 2 Queen Size Beds, and 2 twin air mattress

Popular amenities for Wayne County family-friendly rentals

Kitchen

Wifi

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.94 out of 5 average rating, 263 reviews

A modern villa sits beside a tranquil pond, with warm lights reflecting on the water's surface. The structure features large windows and a spacious patio with outdoor seating. Surrounding greenery enhances the serene environment, providing a peaceful backdrop.

Villa in Jeromesville

Whispering Pines Retreat by Private lake/ Villa #2

5.0 out of 5 average rating, 273 reviews

Tiny home in Dalton

Tiny House on Jericho with Hot Tub

5.0 out of 5 average rating, 141 reviews

Farm stay in Burbank

CF Ranch & Cattle Co.- Lodge and CrossFit Gym

Treehouse in Fredericksburg

The treehouse cabin is elevated among lush greenery, showcasing a robust wooden structure with a spacious front deck. The roof extends gracefully, while the railing details add character. Surrounding trees provide a natural canopy, enhancing the secluded atmosphere of the cabin.

Luxury Treehouse Cabins over Salt Creek - Cabin 2

4.99 out of 5 average rating, 153 reviews

4.89 out of 5 average rating, 243 reviews

Cabin in Apple Creek

Cabin at Saltcreek Pond~Family’s~Fishing~HotTub

4.9 out of 5 average rating, 69 reviews

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

Edinburgh Escape | Hot Tub, Sauna + Fire Pit

A charming white house features a sloped metal roof and is surrounded by a well-maintained lawn. Two large windows on the front allow natural light to enter, while a small staircase leads to the inviting front door, framed by greenery.

4.95 out of 5 average rating, 21 reviews

Country cottage

4.88 out of 5 average rating, 33 reviews

A hot tub with bubbling water is positioned in the foreground, offering a view of a serene pond surrounded by trees. A gazebo with a red-roof is visible across the water, contributing to a peaceful outdoor setting.

Home in Apple Creek

Amish Country Getaway w/ Hot Tub & Views

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 224 reviews

A charming entrance to the separate apartment is featured, showcasing a striped patio umbrella over a small table and chairs. Flower pots flank the windows, adding color to the neutral exterior. A grassy area leads to the door, surrounded by landscaped greenery.

Farm stay in Wooster

Buckeye Ridge Farm -Country Retreat

4.87 out of 5 average rating, 172 reviews

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.

Flat in Wooster

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!