Holiday rentals in Highland Hills

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Top-rated holiday rentals in Highland Hills

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost

The living area features two comfortable gray sofas positioned around a neutral area rug. A world map artwork adorns the wall, while a colorful abstract piece adds visual interest. Natural light fills the space through multiple large windows.

Home in University Heights

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!

FamilyValueAir conditioning

4.82 out of 5 average rating, 167 reviews

Top guest favourite

Flat in Shaker Heights

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.

ValueLocationNearby

4.94 out of 5 average rating, 18 reviews

Guest favourite

Home in University Heights

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.

LocationFamilyIndoor spaces

4.75 out of 5 average rating, 24 reviews

Top guest favourite

A cozy bedroom features a queen-size bed with a light green coverlet. Decorative floral prints adorn the walls. A bedside lamp and a wooden nightstand are positioned nearby. A sliding mirrored closet door reflects the space, adding depth to the inviting atmosphere.

Flat in Chagrin Falls

Cozy Apartment in Charming Village

Cozy apartment with private entrance attached to historic house. Central location in this charming tourist village of Chagrin Falls, a short walk to the natural waterfalls, over 20 great restaurants, two ice cream shops & boutique shopping. Low ceilings & compact bathroom, but full kitchen and parking for one car. Non-smokers only. No pets - out of consideration for future guests. Guests must be able to climb stairs to access apartment. Air conditioning is available during the summer season.

FamilyValueLayout

4.97 out of 5 average rating, 655 reviews

Top guest favourite

The living area features a spacious layout with an orange sectional sofa, a circular coffee table, and a light-colored area rug. Natural light filters through large windows, illuminating the space. A 59" smart TV is positioned across from the seating area, providing a comfortable environment for relaxation.

Flat in Cleveland

Rock 'n' Roll Retreat ~15min to DT~8min Cle Clinic

Unwind in this newly renovated 2BR 1Bath Rock n' Roll retreat in a friendly & vibrant Larchmere neighborhood just 15 mins from the Rock 'n' Roll HOF. This 2nd floor apartment offers a relaxing getaway near restaurants, shops, attractions, landmarks, and major hospitals and employers, making it ideal for your stay in the Cleveland area. ✔ 2 Comfy Bedrooms w/ Queen-Size Beds ✔ Central Air and Heat ✔ Fully Equipped Kitchen ✔ Smart TV ✔ High-Speed Wi-Fi ✔ Washer/Dryer ✔ Parking See more below!

FamilyValueSolo travel

4.93 out of 5 average rating, 135 reviews

Superhost

Home in Bedford Heights

Cozy 3BR | Relaxing Convenient Quiet 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.

LocationValuePool

4.83 out of 5 average rating, 23 reviews

Top guest favourite

Home in Warrensville Heights

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

FamilyLocationParking

4.97 out of 5 average rating, 159 reviews

Guest favourite

A spacious living area features a blue pool table in the center, with a rustic wooden base. On one side, two cozy sofas are arranged for relaxation, and a modern fireplace is visible in the background. Natural light enters through large windows adorned with sheer curtains.

Home in Shaker Heights

5-BR Colonial, King Bed, Main Floor BR, Pool Table

🏡 Enjoy a spacious two-level, 5-bedroom home perfect for families, medical visits, business travel, and extended stays. The main floor offers: A queen bedroom A half bath Upstairs includes: Four bedrooms Two full bathrooms Relax with: A king bed A pool table A foosball table A 58-inch living-room TV A 50-inch primary-bedroom TV Fast Wi-Fi A workspace A full kitchen Laundry Self check-in Parking Sleeps up to 12 registered guests.

ValueFamilyAmenities

4.82 out of 5 average rating, 89 reviews

Guest favourite

A stone fire pit is surrounded by a circular arrangement of natural rocks, with logs integrated into the design. Bright green chairs offer seating nearby, while a gravel path leads to a log cabin nestled among tall trees in the background.

Cabin in Solon

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!!

LocationValueGetting around

4.88 out of 5 average rating, 212 reviews

Superhost

A bright dining area is showcased with a wooden table and built-in cushioned seating. A large window allows natural light to illuminate the space. A world map hangs on the wall, adding an element of global inspiration to the modern decor.

Flat in Cleveland Heights

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.

LocationValueLayout

4.86 out of 5 average rating, 296 reviews

Guest favourite

Home in Chagrin Falls

Luxury|Pool Table|Movie Room|Poker|Nature Oasis

Escape to luxury in this 4-bedroom, 3.5-bath home featuring a spacious living room, dining area, and fully equipped kitchen. Enjoy a home office, lower level with games and movie room, and a master suite with private bath. Outside, explore a nature-filled backyard with a walking trail, creeks, and fire pits. Ideal for relaxation and fun, this home blends modern comfort with stunning outdoor beauty.

LocationFamilyHospitality

4.96 out of 5 average rating, 27 reviews

Top guest favourite

A modern kitchen features warm wood cabinetry and sleek stainless steel appliances. A large window allows natural light to fill the space, highlighting the light-colored countertops. Green plants and decorative items add a touch of color, while a small area rug offers warmth underfoot.

Home in University Heights

Cozy Mid-Century Modern University Heights Getaway

Welcome to our meticulously re-imagined mid-century modern space, where relaxation and style harmoniously come together. This property has undergone a complete top-to-bottom renovation, ensuring that every aspect is refreshed and revitalized. With plenty of space to unwind and recharge, you can truly kick back and enjoy your stay.

LocationValueLong stay

4.97 out of 5 average rating, 137 reviews