Holiday rentals in Medina

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

The Big Blue House-1 block from Medina Square

Welcome to your perfect downtown Medina getaway, just one block off the charming and historic Medina Square. Whether you're visiting for a festival weekend, family gathering or wedding celebration, this spacious and conveniently located home comfortably sleeps up to 14 guests and puts you steps away from everything Medina has to offer, and a public parking garage is right across the street for additional parking availability! Book now and experience Medina the way it was meant to be enjoyed!

Stillwater Retreat-Waterfall·Pond Horses·Firepit

Experience refined living at this elegantly appointed country estate, tucked into a secluded and pristine valley. Surrounded by natural beauty, the property features wooded walking trails that follow the west branch of the Cuyahoga River and offer sweeping views at every turn. Enjoy peaceful mornings overlooking the pond, afternoons exploring shaded forest paths, and golden evenings framed by autumn foliage and stately pines. Blending rustic charm with elevated comfort and private relaxation.

Uptown Liberty I

Uptown Liberty I is a beautiful and unique apartment unit located directly on Medina Square. (Castle Noel is right next door!) This unit features a kitchenette, a full bath and a queen size bed and if you're looking for a bigger apartment and your own garage parking, deck, patio, grill and big back yard we have two more apartments at Liberty Manor within a few minutes walking distance to the historical Uptown Medina Square just look up Liberty Manor ll & lll. it's a hidden Gem!

KING BED*Historic*Charming Updates*Walk 2 Town Sq*

Welcome to our home located in the heart of Historic Medina Ohio! It is a charming 3 bedroom 1 bathroom colonial with beautiful updates and also maintaining much of the home's original character. Located 35 miles south of Cleveland, 24 miles west of Akron and 111 miles north of Columbus. Medina offers a variety of Dining and Attractions within the city and surrounding areas for you to enjoy! Walk to the square and enjoy a variety of events planned throughout the year.

Cottage on the Hill

Welcome to Cottage on the Hill - your home away from home. It has 2900 sf, 4BRs, 5 beds (king, queen, full, 2 twin), den w/ sleeper, living & dining rooms, family room, kitchen, laundry, 3-1/2 baths & a 2 car attached garage. Situated on a secluded 2-1/2 ac wooded site, it is a retreat within the city. Adjacent to Medina's South Town District - just four blocks south of the Historic Medina Square and its many restaurants, bars, coffee shops, specialty shops & events.

Spacious Serene 2Bedroom Retreat

Spacious Serene 2-Bedroom Retreat Welcome to your home away from home! Nestled in a quiet and peaceful neighborhood, this spacious 2bed/2.5-bath home offers the perfect blend of comfort and convenience. Inside the Home Master Bedroom: memory foam king-size bed. A cozy queen-size bed with its own full bathroom close by for added privacy. A warm and inviting space with comfortable seating. Step outside and enjoy a half acre property, surrounded by back woods.

The Hallmark

Charming Retreat Steps from Medina Square Welcome to your home away from home. Enjoy a peaceful stay in a fully furnished space featuring cozy bedrooms, a well-equipped kitchen, and inviting common areas to relax and unwind. Whether you’re in town for a wedding, exploring local boutiques and restaurants, or attending one of Medina’s year-round events, this location is unbeatable. Experience the charm and hospitality that Medina is known for!

Grandma's House at South Town

One mile south of the square in Medina, 30 minutes to CLE, 30 minutes to CAK. Come stay at Grandma's house. Comfy and functional for 7-8 guests. Open first floor with three bedrooms up, enjoy a game of Ms Pacman or Donkey Kong whilst you wait on dinner. This home is new from top to bottom. Full kitchen, new deck, gas grille. Swing outside while the kids play. We hope you enjoy your time here, let us know if you need anything at all.

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

Sleeps 13| HotTub| Historic Renovation| Downtown

Welcome to your Medina retreat! - Historic home near Downtown - Spacious for families & groups, sleeps 13 - Backyard patio w/ hot tub & grill - Bonus game space w/ Xbox One - Full kitchen & dining table - Pet-friendly & family-ready - Free driveway parking for 6 vehicles Step into a home where history and comfort meet in the heart of Downtown Medina.

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.