Holiday houses in Medina County

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

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.

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!

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.

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.

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!

You deserve some R&R @ Buckeye Trail/Rocky River!

Scenic for the Fall! Perfect couple's getaway! This location is perfect for 2 people (but please not 3!) Sandy can give you details about the property as places to go and things to see in the Medina area! Deck overlooking The Rocky River Private Studio Suite overlooks estate grounds down to the Rocky River Very Quiet and private absolute quite hours after 10:00PM out of respect for the property owner and other guests on the property

Cozy Weekend 1BR Haven in Medina!

Welcome to your cozy Medina retreat, where comfort and convenience meet small-town charm. Just four blocks from Medina’s historic town square, this inviting 1-bedroom home offers modern amenities, a warm atmosphere, and plenty of space to unwind. Whether you're here for a romantic getaway, business trip, or family visit, you’ll enjoy a peaceful stay close to local shops, restaurants, parks, and year-round community events.

Trail Side Hideaway In The Woods

Welcome to Trailside Hideaway. Perfect getaway for two located on the bike trail system in Medina. Tucked away in beautiful natural surroundings, this is a private space with a private entrance. Located 2.3 miles from the quaint Square of Medina and next to miles of paved trails and single track bike trails. Bikes can be rented from the local Spin Bike Shop less than a 1/2 mile away.

Medina Square Retreat

Your family will be close to everything when you stay at this centrally-located home in the heart of Medina. Walking distance to Medina Square this home puts you right in the middle of endless options to explore restaurants, bars, shopping, and family friendly attractions. This home is also pet friendly so bring the entire family and get ready to enjoy all that Medina has to offer!