Family-friendly vacation rentals in Wooster

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Wooster

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

A welcoming entrance is framed by a charming wooden fence and lush greenery. A path of stone pavers leads to a white door, flanked by vibrant plants and flowers. Sunlight filters through the trees, creating a serene outdoor atmosphere.

Loft in Ashland

4.99 out of 5 average rating, 223 reviews

Hummingbird Guest Loft

Quaint Guest Loft in the town of Ashland. In the heart of town, within minutes of walking to Ashland University. University is a 5 minute walk. One block from Freer Field with walking paths and where the Ashland Hot Air Balloon Fest is held every July 4th. Short drive to Mochican State Park. Take a hike, mountain bike, ride horses on the many bridle trails, canoe, fish and picnic. Explore the many restaurants, golf courses and farmers market. We will be there for you as often as needed.

Guest favorite

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.

Apartment in Wooster

4.84 out of 5 average rating, 294 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.

Top guest favorite

A vibrant pink bicycle serves as a decorative centerpiece in a garden filled with lush green plants. The bike is surrounded by small lights, and a classic red lighthouse ornament adds a charming touch to the landscape. The entrance pathway leads to the house, framed by greenery.

Guesthouse in Glenmont

4.93 out of 5 average rating, 271 reviews

Glenmont Bike&Hike Hostel

This Airbnb was created for bikers riding on the OTET. This is above a detached garage at zip code 44628. This one open room with a private bathroom includes towels (toilet, shower, and sink). There is a double bed with linens, tv, wifi, mini-kitchen with microwave, sink, and refrigerator. The stove is not working now. The Airbnb is located a few minutes from the OTET/Glenmont Trailhead. Note: NO PETS or children under age 12 allowed. No smoking or vaping allowed in Airbnb.

Top guest favorite

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

4.95 out of 5 average rating, 286 reviews

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.

Guest favorite

A living room featuring hardwood floors and original woodwork. A dark sofa is complemented by two patterned chairs. A coffee table is centered in the space, with a decorative lamp on one side. Artwork adorns the wall above a traditional fireplace, enhancing the cozy ambiance.

Apartment in Wooster

4.9 out of 5 average rating, 131 reviews

Your Home Away From Home l Conveniently Located

Come stay at this cozy, peaceful and inviting home. This is a fully furnished apartment with two entrances, one of which is shared through a common area and one that is a private entrance. You are sure to feel at home with all of the amenities, such as a full kitchen, dining room, living room, etc. We have an onsite manager that will be available to answer any questions or concerns that you may have during your stay. We hope that you come and enjoy your stay and visit again.

Top guest favorite

A comfortable living room is showcased with a light brown sofa and a patterned armchair. A round coffee table is positioned at the center, while a fireplace is framed by decorative items and candles. A TV unit is visible, adding functionality to the space.

Home in Wooster

4.95 out of 5 average rating, 176 reviews

Cozy Home near College of Wooster

Cozy 3 bedroom house near College of Wooster. Five minute walk to Timken Gymnasium or Freedlander Theater and a 10-15 minute walk to downtown restaurants, coffee shops and boutiques. Residential neighborhood near campus. All the amenities you will need for a comfortable and affordable stay. Relax in the living room, enjoy one of three queen size beds along with a fully equipped kitchen and dining area. Also feel free to park in our attached one car garage.

Top guest favorite

Apartment in Wooster

4.99 out of 5 average rating, 185 reviews

Historic Downtown Wooster Victorian Apartment #2

Step back in time to the 1800s in this charming brick Pioneer House in Historic Downtown Wooster. Enjoy the entire first-floor apartment (approx. 1500 sqft), blending vintage elegance with modern comfort. All while being just a block from local eateries, boutique shopping, and historic sites. *Please note there's construction taking place across the street during daytime hours, which may result in some construction noise during your stay.*

Superhost

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

4.89 out of 5 average rating, 122 reviews

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.

Top guest favorite

Loft in Wooster

4.99 out of 5 average rating, 174 reviews

Stunning 2 BR, 2 BA, w/Elevator, Downtown Wooster

Make yourself a home and enjoy downtown living in a beautiful and spacious loft apartment. The 2-bedroom, 2-bath allows much privacy. The main living area is open and has lots of space to spead out with a private entrance elevator. We added a game table or could be used for small dining. The dining area seats 8 comfortably and there is also a den with a 65" TV. The beautiful open kitchen is fully stocked and features a walk-in pantry.

Top guest favorite

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

4.98 out of 5 average rating, 142 reviews

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.

Top guest favorite

A comfortable sofa is adorned with two decorative pillows and a patterned throw blanket. A small side table holds a tissue box and remote control. Soft lighting from a nearby lamp creates a cozy ambiance, and a wall art piece featuring llamas adds a unique touch.

Apartment in Wooster

4.95 out of 5 average rating, 192 reviews

Private, spacious 1 bedroom apt 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.

Guest favorite

A contemporary two-story house is shown, featuring a mix of gray and white siding. A front door with a clean design is flanked by manicured bushes. The surrounding lawn is well-maintained, with a gravel driveway leading to the property.

Tiny home in Holmesville

4.96 out of 5 average rating, 133 reviews

Unique Home in Holmesville/ Holmes County

●20 minutes from Wooster, Millersburg, Berlin, Loudenville, and Mt Hope, and within a short drive to Mohican State Park. ●Firepit and chairs on the back patio ●Built in 2022 with contemporary styling and unique touches throughout. ●Set in the small town of Holmesville with a pizza shop and Blue Moon Bistro close by. ●Quality whole bean coffee provided