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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Guest favourite
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, 297 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.

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, 189 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
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
4.94 out of 5 average rating, 278 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 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
4.97 out of 5 average rating, 184 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 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, 289 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.

Top guest favourite
A four-poster queen bed is centered in the room, complemented by plush bedding and decorative pillows. Soft lighting is provided by bedside lamps on either side. An artwork hangs above the bed, and light-colored curtains frame a window, enhancing the calming atmosphere.
Apartment in Wooster
4.99 out of 5 average rating, 194 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
4.87 out of 5 average rating, 125 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 favourite
The exterior of the apartment displays a well-maintained facade with flowering plants in vibrant hues. A welcoming porch is visible, featuring a seating area. The surrounding lawn is expansive and green, with trees and additional vegetation in the background, enhancing the rural setting.
Apartment in Apple Creek
4.99 out of 5 average rating, 181 reviews

Esther's Amish Country Apartment

Esther's Amish Country Apartment is spacious (960 sq. ft. of living space) located on a beautiful quiet 2 acre property. It has a full kitchen, roomy living room area to relax, queen size bed and walk-in shower; additionally, Armstrong Cable with access Netflix, Prime, Apple TV and excellent WiFi for your entertainment We are an easy 15-20 drive to tourist attractions in the area. *** Read "Other things to note" below for details.

Top guest favourite
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, 147 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.

Guest favourite
A bright living area features light green walls and two windows fitted with two-tone blinds. A dark coffee table sits at the center, surrounded by a gray sectional sofa adorned with checkered cushions. A wall clock and decorative art enhance the space, while a door leads outside.
Vacation home in Smithville
4.85 out of 5 average rating, 217 reviews

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.

Top guest favourite
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, 194 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 favourite
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 homes in Holmesville
4.96 out of 5 average rating, 137 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

Popular amenities for Wooster family-friendly rentals

Quick stats about vacation rentals that are family-friendly in Wooster

  • Total rentals

    30 properties

  • Nightly prices starting at

    $126 CAD before taxes and fees

  • Total number of reviews

    3.2K reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 properties include access to wifi

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