Family-friendly holiday rentals 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.

The Farmhouse Cottage

This cozy Farmhouse Cottage was completely remodeled in recent years and is tucked away on a quiet dead-end street, giving you the opportunity to unwind and relax after a day of traveling. If you’re looking for a peaceful getaway or for a comfortable place to stay while visiting Massillon, Canton, or surrounding areas, then this is your dream house! Berlin is only 30 minutes away. Ohio & Erie Canal Towpath Trail, 26 min. Pro Football Hall of Fame, 17 min. Clay’s Park, 15 min. Wooster, 28 min.

Pleasant View Farmhouse and Pickleball Court

Situated on 80 acres of farm land, this large home is an ideal setting to relax and connect with family and friends! Built in 1904, the house has been restored to much of its original beauty. Aptly named, the setting provides views of picturesque rolling hills and spectacular sunsets. Recently, an outdoor pickleball court was built. Located approx. 20 min. from Canton & from Amish country. It is adjacent to Peacock Ridge, a barn wedding site. It is less than 1/2 mi to the Sippo Valley trail.

Cute n Cozy 2BR House in Massillon *NEW*

This newly remodeled home in Massillon, Ohio is perfect for your next getaway. With a full kitchen, laundry, WiFi and parking- you’ll feel right at home! Centrally located, just a short drive to many nearby attractions: Downtown Massillon, Pro Football Hall of Fame, Ohio's Amish Country, Clay’s Park, Towpath Trail and much more. Rt 21 gives you easy access to Akron, Canton and Cleveland. This home is perfect for couples or families, and the perfect space to relax after a day of exploring.

Park Side Guest House/ Hot Tub/ Outdoor Fire Pit

Welcome to our newly remodeled 2 bedroom 1 bath house in the quiet town of Navarre, next door to a park (UPDATE) recently added a brand new pickle ball court! If you want to burn off some energy, next door to a Deli and more eating places close by, relax in the Hot Tub or go on a hike or bike ride on the bike trail that is just around the corner, the main bedroom has 2 queen beds the small bedroom has 1 queen bed and a full size sleeper sofa in the living room, the kitchen is fully furnished

The Retreat at Barrs Pond

Wake up to nature’s sunny alarm clock after enjoying a peaceful country night in the relaxing atmosphere of this just listed simple yet charming loft. Located 10 mi. To Clay’s Park, 10 mi. to Football HOF, 8mi. to Amish country, 20mi. to CAK airport, convenience in the country! Enjoy catch and release fishing, relaxing by the pond, or simply unwind as you observe the free-range chickens on the property! If you’re simply getting away, the Retreat offers a true remedy for daily stress!

Cozy Modern Apartment

Urban-vintage uptown apartment, fully furnished & located in an attractive & accessible section of Massillon, is ready for your visit. Updated & modern, this space has everything you will need for a comfortable stay. This one bedroom apartment comes with a new queen mattress & a twin sized day bed in the living room area. The living room is open to the kitchen & has a couch, two chairs, ottoman/coffee table, & sofa table. The neighborhood is only short distance from downtown.

A-frame at Creekside Dwellings w/Hot Tub

The A-frame at Creekside Dwellings is a small + impactful oasis near beautiful Amish Country! Only 6 miles from Winesburg + 13 miles from Berlin. There are an endless supply of local attractions. The Pro Football Hall of Fame only 30 minutes away, as well! The A-frame is stocked with all the amenities you will need to kick back and relax! Enjoy the steaming hot tub, gas grill, and tree top views. *note on location: the A-frame is visible from the road during the winter months

Downtown Brick Loft Above The Exchange Coffee Co

Located in the heart of historic downtown Canal Fulton, this charming brick loft will truly take you back in time. Walk or bike to all the local restaurants and shops around town or grab coffee at The Exchange downstairs. The 13 large windows give a panoramic water view of the canal way and downtown. Every detail in this space has been lovingly created with comfort and inspiration in mind. Relax and enjoy this one of a kind location.

This Old House - Lofty Suite

This space I dedicated to my grandmother, and as such I decorated it in a style she would have loved. It is an ideal location for so much, it's within walking distance of some nightlife, stores, a movie theater and rec center. - NO CLEANING FEES** NOTE: this is part of an up / down duplex and as such sound transfers. We have quiet hours and request guests show respect, but it is not perfect.

Amish Country Silo

Experience a one-of-a-kind romantic retreat in a charming grain bin with a modern farmhouse interior. This unique escape offers every amenity to ensure an unforgettable getaway. Gaze out the windows to take in the breathtaking views of the picturesque farmland. You're just 30 minutes from the heart of Amish Country, complete with the best shopping and restaurants!

Stylish 2BR Apt w/ Parking, Near Airport

Stylish two-bedroom apartment with two queen beds, a queen-size sleeper sofa, high-speed WiFi, full kitchen, Smart TV, and free on-site parking. Conveniently located just 5 minutes from I-77 and CAK Airport, and 10 minutes from the Pro Football Hall of Fame. Perfect for families, business travelers, or extended stays. Read more below!