
Holiday houses in Highland Hills
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Highland Hills
Guests agree: these stays are highly rated for location, cleanliness and more.

Relaxing Gem near CLE Clinic & Van Aken District
Unwind in this newly renovated 2BR 1Bath mid-century modern oasis in a friendly & vibrant Shaker Heights, OH neighborhood. This 1st floor apartment offers a relaxing getaway near restaurants, shops, attractions, landmarks, and major hospitals and employers, making it ideal for traveling nurses and business travelers looking for an extended stay. ✔ 2 Comfy Bedroom w/ Queen Beds ✔ Relaxing Living Area ✔ Fully Equipped Kitchen ✔ Smart TV ✔ High-Speed Wi-Fi ✔ Washer/Dryer ✔ Parking See more below!

The Farmhouse - 1 Bdrm Apt in a Great Location
Welcome to this 2nd flr 1 bd/1 ba private apartment in a charming 1880s farmhouse located in a friendly walkable neighborhood. Full kitchen with all you need to make your own meals, washer/dryer and separate office inside the unit. Free off-street parking. You are only: 5 min walk to Starbucks, a variety of restaurants, bars, shops, trails 5-10 min drive to Cleveland Clinic, University Hospitals, Case Western, museums, parks, Little Italy and more 15 min drive to major attractions and Lake Erie

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.

Historic Little Italy Garden Apartment
Stylish garden apartment. This retreat blends modern comfort with the vibrant cultural charm of Historic Little Italy. Steps away from shops, restaurants, and lively bars. Wade Oval Park is a nearby cultual hub, home to The Art & Natural History Museums and Botanical Gardens. Easy access to Case Western Reserve, Cleveland Clinic and University Hospital. Walk to the beautiful Lakeview Cemetary or take transit downtown to 4th street. Perfect for short or long stays. Book for a memorable time.

Upscale 2Br Near Van Aken/Hospital/CWRU (2nd FL)
This newly renovated 2BR 1Bath home is located in a safe, peaceful and friendly neighborhood in the heart of Shaker Heights. Our home offers great convenience and is surrounded by the area's best shopping and dinning - walking distance to Heinen's and CVS; 5 minutes to Van Aken District; 10 minutes to Beachwood and Pinecrest; 15 minutes to Cleveland Clinic, UH, University Circle, Orchestra, Art Musem; and close to major employers. It is situated near public transportation, I-271 and I-480.

Near hospitals colleges food bars w/garage space
Welcome to brand new suite! This Spacious , stylishly furnished 1-bedroom apartment is located in safe neighborhood, in the famous Cedar-Lee area, at the heart of Cleveland Heights. This unbeatable location is walking distance to multiple cafes, wineries, and restaurants, Cedar-Lee Theater, CVS, Cleveland Heights-University Heights Library, and more all within blocks. < 3 miles from Cleveland Clinic, University Hospitals, Case Western University; and <7 miles from downtown Cleveland.

Historic District 2BR on 1st Floor near CLE Clinic
Get cozy in this 2BR 1Bath historic district charmer in a friendly & vibrant Shaker Heights, OH neighborhood. This 1st floor apartment offers a relaxing getaway near restaurants, shops, attractions, landmarks, and major hospitals and employers, making it ideal for traveling nurses and business travelers looking for an extended stay. ✔ 2 Comfy Bedrooms w/ Queen Beds ✔ Relaxing Living Area ✔ Fully Equipped Kitchen ✔ Smart TV ✔ High-Speed Wi-Fi ✔ Washer/Dryer ✔ Parking See more below!

Cozy Heights Oasis-Walk to Restaurants
Private and cozy second floor 2 bedroom spacious unit in the Cedar-Lee district of Cleveland Heights. Completely refurbished. Walk to restaurants on Lee Road or Cain Park. Open the windows and listen to a chorus of birds-a true oasis from the hub-bub. A private patio and outdoor living right off the living room. Note: Quiet hours after 10 p.m. This unit is not suitable for partying, loud music and disruptive behavior that impacts neighbors or guests in other apartments.

Cozy, deadend street. Close to everything!
*HOUSE IS ntentionally BASIC IN EVERY WAY - THIS IS FOR DOGS FIRST. Intentionally NOT LUXERIOUS. Basic in decor. Furnished with all basics- kitchenware, dishes, pots, pans, silverware. Towels, bedding, etc. Located in the middle of "The Heights", you are within a 1/2 mile to restaurants, bars, movie theatre. Great location for medical residence, as it's close enough to Cleveland Clinic and UH, but in a fun, affordable neighborhood. *NOTE: AC is portable units-not central

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

Cozy and Quiet Apartment
Relax in this cozy and roomy one-bedroom apartment located in the charming and culturally rich neighborhood of Cleveland Heights. This area boasts a variety of acclaimed restaurants, lively bars, unique shops, and local attractions. From this centrally-located apartment, explore the vibrant neighborhoods of Cleveland Heights, Little Italy, Coventry, University Circle, and Downtown Cleveland. When it's time to unwind, come back to your cozy retreat.

[B] Sky Light | Cozy 1BR Apt, TOP | Coventry Area
Welcome to our modern 1-bedroom city apartment, situated just a short distance from the vibrant downtown area. Relax in the comfortable living room and enjoy the convenience of being close to the city's attractions without the hustle and bustle right at your doorstep. Our apartment is ideal for couples or business travelers looking for a comfortable and well-located stay.
Popular amenities for Highland Hills holiday rentals
Other great holiday rentals in Highland Hills

Downstairs Unit to Remodeled Townhome

1913 tree house - Redbud Room

Home away from home 5

Relaxing Stay for Traveling & Local Workers

Superior Room

Charming 2 Room Suite, Private Bath

Willow Retreat

Updated 1920's charmer
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Washington Holiday rentals
- Mississauga Holiday rentals
- Grand River Holiday rentals
- Northeast Ohio Holiday rentals
- St. Catharines Holiday rentals
- Niagara Falls Holiday rentals
- Indianapolis Holiday rentals
- Pittsburgh Holiday rentals
- Erie Canal Holiday rentals
- Detroit Holiday rentals
- Cuyahoga Valley National Park
- Rocket Mortgage FieldHouse
- Cleveland Browns Stadium
- Rock & Roll Hall of Fame
- Progressive Field
- Pro Football Hall of Fame
- Headlands Beach State Park
- Little Italy
- Mosquito Lake State Park
- Cleveland Metroparks Zoo
- Punderson State Park
- Boston Mills
- Cleveland Museum of Natural History
- Gervasi Vineyard
- Cleveland Botanical Garden
- Agora Theatre & Ballroom
- Laurentia Vineyard & Winery
- Case Western Reserve University
- Debonné Vineyards
- The Arcade Cleveland
- Playhouse Square
- Cleveland Museum of Art
- Huntington Convention Center of Cleveland
- Edgewater Park Beach




