Pet-friendly holiday rentals in Wooster

Lovely Private Home w/ Cozy Farmhouse Charm

Come away & enjoy a peaceful, refreshing stay at Vivian’s Serenity Guest House. Nestled in among the rolling hills of Amish Country, cozy up in the inviting house & explore local attractions. Only 1.5 miles from Rails to Trails biking trail, moments to historic downtown Millersburg, 10 minutes to Berlin shopping and great food! 1 mile to the Holmes County Fair Grounds. Whether you’re ready to shop unique boutiques or relax, Serenity House offers seclusion & proximity to all Amish country offers!

Family Comfort!Trails,W/D,Pets,Extend Stay&Coffee!

Book with someone you can trust! Proud to meet Massillon City requirements - inspected and certified Airbnb! Cozy atmosphere to gather for quality time with friends & family. Cooking essentials provided for a home made meal! Walk to gas station, restaurant & Downtown! 2 min to Hwy! Maximum convenience! Large back yard for kids & pets to play. Small, fenced lounge area with grill off of kitchen. Perfect for families, business & extended stays! Review all listing info before booking. Thx!

Romantic private cabin w hot tub in Amish Country

Retreat to the Fresno Escape! A private cabin featuring a year-round hot tub, perfect for relaxation. Tucked among pines and rocks in the heart of Amish country, where the occasional clip-clop of horse and buggies adds charm. Styled like a railroad depot, the artistically furnished home displays intricate stonework, tile and custom stained glass. The kitchen includes appliances and cookware, with the outdoor area offering a propane grill. Complimentary firewood is provided for the firepit.

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.

Entire Home Highland Square/CVNP

Enjoy a comfortable experience at this centrally-located home 1 block away from the strip in Highland Square. Central air, 2 bedrooms with brand new queen beds. Large kitchen with dishwasher. Netflix & Prime Video on tv's. Comfortable leather couches, front and back deck, and fire pit. Being 5 minutes from Downtown Akron, 35 minutes from Downtown Cleveland, and 10 minutes from Cuyahoga Valley National Park, there is a lot of nightlife, hiking and biking in the area. All are welcome!

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.

The Lux - tiny home w/ jacuzzi in Berlin

The Lux is our largest and most luxurious tiny home. At 32 foot long, it looks striking from a distance. The butterfly roof and accent walls give you a hint of what to expect when you walk in. The Lux has all the basics you’d expect for a luxurious stay: full bathroom with running water (not a composting toilet) a full kitchen, heat/AC, fast wifi & a memory foam queen size bed. But it’s what you wouldn’t expect in a tiny home that will get you.

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.

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.

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!

Pav's Place 1BD/1BA Private w/Queen Bed!

Welcome to your home away from home in Akron! This renovated duplex was built in 1919 and is located in a safe & calm residential neighborhood. Easy access to downtown, exploring Cuyahoga National Park or seeing a show at Blossom. Student or traveling medical professional? Akron University, Cleveland Clinic and Summa Health are all within a 5min drive.

Cozy 1 bedroom in Highland Square, pets welcome!

This unique 1 bedroom is in the heart of Highland Square. Quiet street just steps away from great locally owned restaurants, shops, and a fresh food market. Live music and other entertainment nightly! Minutes from I-77 & I-76. Full kitchen & bathroom. Queen mattress is brand new.