Holiday houses in Highland Hills

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Top-rated holiday rentals in Highland Hills

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Guest favourite
A modern living area features a comfortable sofa with cushions, two cozy armchairs, and a coffee table. Large windows allow natural light to fill the room, enhancing the neutral color scheme and contemporary decor. A television stands on a sleek entertainment unit, completing the inviting space.
Apartment in Shaker Heights
4.93 out of 5 average rating, 174 reviews

Modern & Comfy ~ Close to CLE Clinic ~ Long-Stays!

Unwind in this newly renovated 2BR 1Bath modern-industrial oasis in a friendly & vibrant Shaker Heights, OH neighborhood. This 2nd 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!

Guest favourite
A charming three-story brick home showcases a Tudor architectural style. The front features dark wood accents and a covered entryway, set against a well-maintained lawn. Trees provide shade, enhancing the warmth of the inviting exterior on a sunny day.
Apartment in Shaker Heights
4.89 out of 5 average rating, 70 reviews

Peaceful Cleveland Home | 2–90 Day Stay | Near Cle

Peaceful • Convenient • Perfect for Short or Extended Stays Whether you’re in Cleveland for a weekend, a medical visit, a job assignment, or home repairs, this quiet Shaker Heights duplex has everything you need for a comfortable stay. Whether for a few nights or a few months. Just 15 minutes from Cleveland Clinic, University Hospitals, and downtown, it’s fully furnished and stocked, professionally cleaned, and designed to feel like home. ⸻ 💰 Stay & Save • 7+ nights: Save 10% • 28+ nights: S

Top Guest favourite
A bright living room features a cozy orange sofa paired with two armchairs adorned with patterned cushions. A wooden coffee table sits in the center, complemented by a decorative rug. Natural light filters through the windows, enhancing a welcoming atmosphere.
Apartment in Cleveland Heights
5 out of 5 average rating, 183 reviews

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

Guest favourite
A cozy living area features two black chairs and a beige sofa, complemented by a circular glass coffee table. The walls are painted white, creating a bright atmosphere, while the sloped ceiling adds character. A small kitchenette is visible in the background.
Apartment in Shaker Heights
4.91 out of 5 average rating, 139 reviews

Small and Cozy 1BR Near Cleveland Clinic~Safe Area

Relax in this newly renovated 1BR 1Bath unique efficiency in a friendly, safe & vibrant Shaker Heights, OH neighborhood. This upper level unit offers a relaxing getaway near excellent restaurants, shops, attractions, landmarks, major hospitals and employers, making it ideal for traveling nurses and business travelers looking for an extended stay. ✔ Comfy Bedroom ✔ Relaxing Living Area ✔ Basic Kitchenette ✔ Smart TV ✔ High-Speed Wi-Fi ✔ Air Conditioning ✔ Washer/Dryer ✔ Parking See more below!

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.
Apartment in Chagrin Falls
4.97 out of 5 average rating, 597 reviews

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.

Guest favourite
A modern living area features a comfortable gray sectional sofa and a light wood TV stand, positioned beneath bright artwork. A round coffee table sits on a patterned area rug, while natural light enters through large windows dressed with sheer curtains. A stylish armchair and decorative shelf add character.
Home in South Euclid
4.92 out of 5 average rating, 52 reviews

Light, Bright, and Clean! Close to it all!

Discover our light, bright, and cozy home in a walkable and safe neighborhood! Ideal for traveling nurses, digital nomads, or families new to the city, this retreat has been renovated and furnished with your needs in mind! Travel Times: Cleveland Clinic: South Pointe: 14 min Hillcrest: 15 min Main -University Circle: 15 min Sports & Marymount: 24 min University Hospitals: Main: 14 min Ahuja Medical Center: 14 min The rest within 20! MetroHealth: Cleveland Heights: 7 min The rest within 20!

Superhost
A cozy living room is equipped with a flat-screen TV mounted above a white fireplace. Natural light filters through multiple windows adorned with beige curtains. A blue sofa and armchair provide comfortable seating, while a wooden table offers a surface for various activities.
Apartment in Shaker Heights
4.68 out of 5 average rating, 128 reviews

Cozy 2BR Near Cleveland Clinic | Pet Friendly

🏡 2 Bedrooms • 1 Bathroom • Sleeps 4 📍 15 Minutes → Cleveland Clinic & University Circle 🍳 Fully Stocked Kitchen – Gas Stove, Microwave & Cookware 🛋 Cozy Living Room w/ RokuTV for Streaming 💻 Full Work Desk + Fast Wi-Fi – Great for Remote Work 🚗 Off-Street Parking for 1 Car + Free Street Parking 🐾 Pet-Friendly Stay – Furry Friends Welcome! Whether you’re here for a medical visit, work trip, or local adventure, this charming apartment offers everything you need for a comfortable stay!

Guest favourite
A spacious living area is presented, featuring a comfortable sofa and a soft area rug. A modern coffee table sits in the center, while a large TV is positioned against the wall. Natural light filters in through sloped ceilings and a nearby window.
Apartment in Cleveland Heights
4.99 out of 5 average rating, 94 reviews

New! “Modernistic Retreat”

Elevate your stay in this bright, elegant and spacious 3rd floor apartment that offers the perfect blend of tranquility and urban convenience. Less than 10 minutes from Cleveland Clinic, 8 min from Case Western University, 17 min from Rock and Roll Hall of Fame, 18 min from Cleveland Browns Stadium, 20 min from Downtown, 28 min from Cleveland Airport and 45 min from Blossom Music Venue. Moments from charmed local neighborhoods such as Coventry, Little Italy, Cedar Fairmont and Lee Rd.

Top Guest favourite
A welcoming entrance leads to a sunny sitting room featuring a blue sofa beside a wooden rocking chair. A small side table with a lamp is visible near a large window framed by soft curtains, allowing natural light to enter the space.
Guest suite in Cleveland Heights
4.96 out of 5 average rating, 502 reviews

Private Victorian suite with two rooms and a bath

You’ll love this newly remodeled third floor suite in our large century home located near Coventry Village/University Circle/Cleveland Clinic. The private suite with separate entrance and stairs has an air conditioned large bedroom with a firm queen bed, a sunny sitting room with a futon and a bathroom (shower) finished in Victorian ornate wood trim! Off street parking is in the rear. Our place is great for couples or business travelers, and the futon can sleep a child or adult.

Top Guest favourite
An entertainment lounge is featured with a space-themed mural depicting an outer space view. Red accent lighting highlights the modern seating area, which includes a red couch and light-colored coffee tables. A large TV is mounted on the wall, enhancing the inviting atmosphere.
Home in Warrensville Heights
4.97 out of 5 average rating, 125 reviews

NEW! Stylish Galactic Getaway

Enjoy your stay at a newly updated Lux Airbnb! Surrounding Locations: - Cleveland Clinic | 20 mn - Pinecrest | 6 mn - Beachwood Place | 10 mn - Legacy Village | 10 mn - Hopkins Airport | 20 mn Housekeeping/Guidelines: - Before check-in, the unit will be thoroughly cleaned and inspected. - We ask you to treat our Airbnb with respect as if it was your own. - Damaged/Stolen items = Additional Fees. - The home's security code will be issued upon the reservation date. - No Smoking!

Superhost
The entrance features a white door with a decorative window, flanked by two black chairs adorned with blue and white cushions. A small plant adds a touch of color to the brick exterior, which showcases a warm, inviting atmosphere.
Apartment in Shaker Heights
4.82 out of 5 average rating, 17 reviews

Shaker Heights Apartment near Cleveland Clinic

Furnished apartment, one bedroom, one full bath. Completely remodeled lower level unit with new appliances, full eat-in kitchen, fireplace, mantel, garage, onsite laundry facility and secured entry. It is a lower level apartment so think hobbit house for cozy northern stays. Yes some doorways are 6 but overall a basement apartment. Perfect for a professional seeking a convenient stay near the city in a quiet residential neighborhood.

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
4.87 out of 5 average rating, 182 reviews

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!!

Popular amenities for Highland Hills holiday rentals

  1. Airbnb
  2. United States
  3. Ohio
  4. Cuyahoga County
  5. Highland Hills