Holiday rentals in Guilford Township

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Come and Play at pet friendly Chippewahoo!

Have fun with the whole family at this stylish place. Grilling, cornhole, firepit and more! You can see Ohio's largest natural lake from the road. The Village of Chippewa Lake has playgrounds, beach access with the provided pass, tennis and pickleball, and of course, walks along the beautiful lakeside. A peaceful retreat while still conveniently located near Medina, Cleveland and Akron. Open floor plan and covered patio provide lots of opportunities for entertaining. Fenced in yard for your pet

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Guest favourite

Liberty Manor Il

This beautiful 144 year old newly remodeled historical manor retains all of the original charm but has been updated to include the modern amenities we have grown accustomed to. great for traveling nurses, work, extended vacations, long or short term rentals are negotiable upon request, just a few minutes walk to historical downtown Medina square with all the fine restaurants, shopping, Castle Noel and more all within walking distance, look up Medina square for all upcoming festivals and events!

Elegant Boho apartment in downtown Orrville

Retreat to the harbor. We created this space with you in mind and are always updating and adding to it for your comfort. When we travel, we seek Airbnb, a unique spot that allows us to relax and enjoy the moments. So when we bought this apartment, we knew from the start it needed to be for guests, offering a place of comfort and rest. We renovated the bathroom most recently, and we continue to enhance it to make it great for you. Located right in downtown Orrville, this is ideal for stay!

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The JoKo Cottage

Welcome to our cozy little cottage built in the early 1930’s by a then well-known artist, Joe Koch (JoKo was his artist name). Joe designed and built the cottage and is full of his unique style. It was featured in 1950 in The Akron Beacon Journal with lots of pictures! All of the wormy chestnut wood (wood with holes in it) is original to the cottage. Even the tile by the fireplace is original. In this place many beautiful things were created. We hope you find beauty here too!

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Guest favourite

Lake Retreat Cozy Modern Big Driveway Pet Friendly

Cozy, newly built lake house perfect for families and friends seeking a peaceful, relaxing escape. Just steps from the lake, this inviting home features a large driveway, pool table, grill, a private fire pit, and a warm, comfortable atmosphere. Enjoy a clean, modern, fully stocked space with fresh towels, toiletries, kitchen essentials, and a free washer and dryer. Enjoy easy parking, nearby attractions, and room to relax with plenty of space for everyone to unwind comfortably.

The Great Medina Cabin -SLEEP 16

Escape to this spacious and peaceful all-wood cabin retreat in Medina, Ohio—perfect for families, friends, and groups up to 16. Surrounded by open land with no neighbors in sight, the cabin features 4 bedrooms, 4 bathrooms, 3 living rooms, a game room, hot tub, and fire pit. Enjoy a fully stocked kitchen, fireplace, massage chair, and even an old fire truck on-site. Handicap accessible and designed for comfort, this unique getaway blends rustic charm with modern relaxation.

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Guest favourite

Wadsworth Townhome 3 bed 2.5 bath

Wadsworth Townhome 3bed, 2.5 bath. Great neighborhood close shopping - sleeps 10 Wadsworth Townhome 3bed, 2.5 bath. Great neighborhood close shopping - sleeps 10 The main floor has a great room and rear patio. The upper level has new appliances in the kitchen, dining room, and half bath. The second story has an owner’s suite w/ remodeled full bath, 2 additional bedrooms, full bath, and laundry w/ washer & dryer. Partial basement w/gas furnace, AC, and gas water heater.

The A.T. Spitzer House

Welcome to the historic AT Spitzer House, built in 1880 and nestled in Medina’s charming Banker’s Row neighborhood, just two blocks from Medina Square. This Queen Anne-style Victorian home features 5 bedrooms, 2 bathrooms, and comfortably sleeps up to 10 guests. Enjoy the perfect blend of historic character and modern comfort, with shops, restaurants, festivals, and attractions just a short walk away. Step inside and experience a glimpse of Medina’s past!

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.

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Guest favourite

Sycamore Hill

Relax with the whole family at this peaceful place to stay. Cabin sits on 4 acreas of hill and wooded areas. Main guest area has many new updates including new kitchen, new master bath, updated main bath with tankless hot water heater, new floors, lighting, window blinds, and gas fireplace. 4 Bedrooms feature 1 King Size Bed, 2 Queen Size Beds, and 2 twin air mattress

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Guest favourite

Star Lane garden apartment with pool

Enjoy a peaceful stay in a quiet neighborhood at the end of a dead‑end street. Just 5 minutes to the highway and 40 minutes to Cleveland Airport. Close to Portage Lake State Park, River Styx Park, Hinckley Reservation, Cuyahoga Valley NP, and Akron University. Golf courses nearby, plus Amish Country attractions. A safe, family‑friendly base to explore the area.

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Guest favourite

Charming restored country farmhouse

Relax in this peaceful and serene country setting. Ridgetop golf course across the street, house has a fire pit, that will be stocked in season, feel free to sit by small lake. Great local restaurants and wineries near by. We pride ourself on the cleanliness of our home and we are confident you will love staying here.