Holiday rentals in Highland Hills

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.

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. Located in a safe/historic neighborhood. Apartment is located on 3rd floor of a Tudor house, some stairs are required to access.

Modern Farmhouse Chagrin Falls Beachwood CVNP

Private Custom-Renovated Modern Farmhouse tucked into a wooded setting minutes from downtown Chagrin Falls and Hunting Valley. Neighboring Beachwood, Moreland Hills & Pepper Pike. 20min to Cuyahoga Valley National Park. Heated slate floors, spa like bath with endless hot water, dual work spaces & true privacy. Affectionately dubbed “The Wayback,” this home sleeps 6 with 2 private bedrooms, a fully equipped kitchen, and upscale amenities near Pinecrest & ETON dining, shopping, and entertainment.

Stay at Supreme!

Enjoy a comfortable and convenient stay in the heart of Beachwood. Located just minutes from Cleveland Clinic and University Hospitals, beautiful parks and nature trails, and top shopping and dining at Pinecrest and Eton Malls, our home is perfectly situated for both short and extended stays. The house is minutes from local synagogues and kosher restaurants. A spacious, fully renovated home, with a modern touch. It’s an ideal place to relax and feel at home—no matter the reason for your visit.

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.

Leather Recliner | FREE Garage Parking | Updated

Step into comfort and style in this beautifull home. Unwind after a long day on the luxurious leather reclining sectional, perfect for cozy evenings or movie nights. With six plush beds, restful sleep is guaranteed for every guest. Each room is designed with your comfort in mind, with a desk, chair, TV, chest of drawers, and other furnishings to make your more convenient. Whether you're here for work or leisure, this home offers the perfect blend of comfort and tranquility.

Cozy Quiet Ranch with Sprawling Yard

This cozy ranch has undergone a complete renovation and sits on a quiet street that dead ends into the Metro Park bridle trails. This unit features comfortable furnishings, all new stainless steel kitchen/laundry appliances, and comes with a huge back yard that frequently gets visited by wildlife. This house is only a 10-15 min walk from Bedford's historical district that has been featured in Architectural Digest as one of the top 30 most beautiful main streets in America.

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!!

South Euclid Home 10 Minutes to Cleveland Clinic

Located just a 5-minute drive from The Beachwood Mall and a 2-minute walk to the vibrant Cedar-Warrensville shops, bars, and restaurants, this home offers convenience at its best. CVS, Whole Foods, and the local library are all within walking distance. Plus, you're only 10 minutes away from the Cleveland Clinic, University Hospitals, the Cleveland Orchestra, and The Cleveland Museum of Art.

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.