Holiday rentals 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!

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.

Quiet Cozy 3BR | Relaxing Convenient Getaway

Just seconds from the highway, drive to visit nearby Cuyahoga Valley National Park, casinos, Cleveland Clinic, & University Hospital, & Pinecrest shopping. 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 space will make you feel right at home. Message for booking dates more than 60 days away.

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.

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.

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!!

The Maproom Room | 10 Mins to Cleveland Clinic, UH

🗺️ Map-themed studio • Sleeps 2 ✨ Fully renovated • Clean + modern ☕ Kitchenette • Coffee maker • Microwave & Instapot 📺 Smart Roku TV + streaming apps 🚗 Off-street parking for midsize cars (1 spot) 📍 10 min to Cleveland Clinic + University Circle Modern comfort meets world travel charm in this map-inspired studio apartment — thoughtfully designed and ideally located near Cleveland’s best cultural attractions.