Pet-friendly holiday rentals 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!

Make this cozy, spacious apartment your home away from home. Centrally located between Downtown and Uptown Wooster. This home is with in walking distance of West View Manor and the Wooster Country Club. This convenient location gives you easy access to restaurants, shopping centers, the YMCA, the College of Wooster as well as Wooster High School all within 3 miles. It's perfect for one person or bring the whole family. Stop in for a visit and enjoy all the great city of Wooster has to offer!

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.

Lake Studio Casita

Welcome to Portage Lakes retreat! Enjoy the fire pit, hot tub, Swedish sauna, cold plunge and patio dining with an amazing water view! Super cozy studio guest apartment with a living room/dining room. TVs in both the living room and studio bedroom. Bring your own boat or enjoy the paddle boards we have here on the property. Walking distance to several different awesome restaurants! Hot tub and sauna are down the stairs on the below deck and free for guests to use!

The Sapphire- dog friendly home in Chippewa Lake

Welcome to the Sapphire! 500 foot walk to Chippewa Lake! -Family & dog friendly -3 bedroom/1 bathroom home -Back porch & fenced in backyard -Fully equipped kitchen -3 off street parking spots -Wifi -8 minute drive to public boat launch -12 minute drive to historic Medina, Ohio -4 minute drive to The Oaks Lakeside Restaurant/Wedding Venue I'm here for you during your stay, but our level of interactions is up to you. I'm only a phone call/message away.

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.

Spacious 2 Bedroom House

Spacious two bedroom house in a quiet neighborhood away from city noise and only 7 minutes away from Downtown Akron where many go for dining and experiences. There is plenty of parking in the driveway. We offer many amenities and the property is fully secured. Beautiful, tranquil fish pond outside to admire on warm summer days in Ohio. There will be someone available at all times to assist you if you should need anything.

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.

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.