Holiday rentals in Highland Hills

Cottage in the Village * Walk to shops/restaurants

This cute little century home (1000 sq. ft.) is located on a quiet street just steps from the shops and restaurants in the village. Park your car and walk to the falls, grab a bite to eat, and explore. Back at the house, grab a book and read on the covered front porch, or relax in the sun on the back deck. The lower level yard has a fire ring to roast marshmallows and a circular staircase leading up to a playhouse for the kids. This cozy spot is the perfect place to be to explore Chagrin Falls!

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.

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.

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.

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!!

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.

Maple Heights Getaway

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!

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.