Holiday houses in Highland Hills

High Road Retreat

Welcome to our sweet retreat! My daughter and I have created a cozy space where you can feel right at home! This newly renovated, entire home with 2 bedrooms, is conveniently located just outside of Cleveland, and a short 5-minute drive from the highway in a quaint and quiet neighborhood. Whether you’re traveling for a music concert, sporting event, exploring the city, discover our vast hiking trails, require a place if a loved one is in hospital, or a traveling nurse, we are centrally located!

The Worlds Cozy Nest

Rest and relax in this calm, stylish space. Sitting right in the heart of one of Cleveland’s most prestigious, safe suburbs, University Heights. This cozy home is Less than 15 minutes from Cleveland clinic and University hospitals main campus. Walking distance from plenty of shops and restaurants and less than 10 minutes from Legacy Village and Beachwood Mall, two of Clevelands premier, upscale shopping areas. This house has been newly renovated and comes equipped with all essentials plus more!

Quiet Cozy 3BR | Relaxing Convenient Getaway

Just seconds from the highway, drive to visit nearby Cuyahoga Valley National Park, Pinecrest shopping, casinos, Cleveland Clinic, & University Hospital. Welcome to this spacious, centrally located retreat in Bedford Heights—a quiet neighborhood less than 20 minutes drive to Downtown Cleveland, & outdoor adventures. Perfect for medical recovery, family fun, traveling professionals or extended stays-this property will make you feel right at home. Message for booking dates more than 60 days away.

Log Cabin I Nature's Oasis I Fire Pit + Gazebo

🌲 3 bedrooms • 4 beds • 1.5 bathrooms • Sleeps 6 🔥 Stone patio • fire pit • screened-in gazebo 🍳 Fully equipped kitchen • double ovens • eat-in dining 🪵 Log cabin vibes • nature views in every room 🪟 All-seasons room w/ game table + lounging area 🚗 Driveway parking for 5 cars + carport 📍 Next to Euclid Creek Reservation • 20 min to Downtown CLE Subtly tucked away, this mid-century log cabin offers peace, space, and a true connection to nature — all just minutes from Downtown Cleveland!

The Lake House

** We do not allow weddings (including “micro”), parties, or events of any kind. ** 10 minutes from downtown! DIRECTLY on Lake Erie's shoreline, cantilevered above the water. Completely private waterfront escape. Experience the sound of the waves for a truly relaxing getaway. THE VIEW - Panoramic views of Lake Erie and surrounding wildlife. Dreamy sunsets. THE INTERIOR - The meticulously designed interior blends the timeless charm of mid-century modern architecture with high-end luxuries.

Chagrin Falls Private Suite

Private in law suite on 2 acre wooded setting in Bainbridge Twp., just minutes to historic Chagrin Falls and easy access to freeway to head downtown to explore downtown Cleveland. Suite has full kitchen, private bath with walk-in shower, 1 bedroom with queen bed and walk-in closet, covered parking, patio area with fire pit. Main home is occupied by hosts and suite has private entrance but shared laundry room (available for extended stays) that connects main home to suite with locking doors.

Modern & Peaceful Loft | Private Entrance

You’ll experience comfort and privacy in this renovated Shaker Heights studio, just minutes from Cleveland Clinic. Professionally designed for peaceful stays with a private entrance, $5k+ countertops, fridge & freezer, microwave, $1k+ queen bed, soft close cabinets, firm mattress, etc. Enjoy fast Wi-Fi, secure self check-in, perfect for medical visits, work trips, in a safe/historic neighborhood. Apartment is located on a 3rd floor of a Tudor house, some stairs are required to access.

Rare Cleveland Apt: Little Italy! W/Sauna&Hot tub!

Fall in love with this charming, newly updated 1-bedroom, 1-bath lower unit triplex apartment situated in the heart of Little Italy, walking distance from University Circle, UH Hospital, Cleveland Museum of Art, Botanical Garden, Public Transportation and much more. Apartment is complete with a well-equipped kitchen, Smart TV, laptop workspace, and modern furnishings, this vacation/business rental delivers all the essentials so you can spend more time relaxing and exploring.

Star Wars–Themed Home w/ Arcade | Family-Friendly

Enjoy your stay at a newly updated Star Wars–themed family home- perfect for relaxing getaways, extended stays, or families needing comfortable temporary housing nearby. 📍 Nearby: • Cleveland Clinic – 20 min (medical stays & visits) • Pinecrest – 6 min (dining & shopping) • Cuyahoga Valley National Park – ~20 min (trails & scenic railway) • Downtown Cleveland – ~20 min (museums & sports) • Hopkins Airport – 20 min (easy travel access) 🚭 Smoke-free & pet-free home

Little Black Cabin in the woods

We have a 900 sq.ft. , log cabin in the woods. The woods of Solon, OH. A southeast suburb of Cleveland. The cabin has 2 bedrooms, each with a queen bed and lots of built in cabinets. They share full bath. As you enter the mud room, to the right is a laundry room with washer & dryer, straight ahead the great room complete with a stone fireplace lots of windows and a small functional kitchen. Welcome to your home in the woods!!

Maple Heights Serenity

Conveniently situated near Cleveland, this place offers both comfort and easy access. Just a short drive to downtown, the airport, Edgewater Beach & Lake Erie. Close to shops, restaurants, parks, and family fun centers. Features a modern kitchen, Wi-Fi, and a SMART TV (log into your own Roku). Shared washer/dryer (paid use). No cable; don’t forget to log out before checkout. A great spot for work or relaxation!

Swanky Mid-Modern Hideaway-Walk to Restaurants

Kick back and relax in this calm, stylish space - completely renovated with today's travelers needs in mind. We've kicked it up a notch and can't wait to share this space with you! We lovingly call this property the beehive because of our fun yellow front door!! Walk to Lee Road restaurants. Three miles to Cleveland Clinic.