Holiday rentals in Highland Hills

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Top-rated holiday rentals in Highland Hills

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Guest favourite

Flat in Shaker Heights

4.89 out of 5 average rating, 57 reviews

Quiet Cleveland Stay • 1st Floor + Porch

Peaceful • Convenient • Designed for Extended Stays Perfect for travel nurses, remote work, or family visits—this quiet Shaker Heights duplex is just 15 minutes from Cleveland Clinic and full of thoughtful touches to help you feel at home. 💰 Long-Stay Discounts: Stay 7+ nights and save 10%, or 28+ nights and save 25%. Enjoy a private first-floor unit with cozy bedrooms, a stocked kitchen, fast Wi-Fi, a dedicated workspace, and a peaceful three-season porch. The upstairs unit is unoccupied, of

Top guest favourite

Home in Willowick

4.96 out of 5 average rating, 261 reviews

Lake Erie Getaway

Enjoy the wondrous beauty and sunsets of Lake Erie, the 11th largest freshwater lake in the world. From the back yard you can swim or fish. 2 bedroom/2 bathroom house with cozy electric fireplace in family room . 1300 square feet of first floor living on Lake Erie.Lake views from nearly every room. Private fenced backyard with over 400 plants. Twenty minutes from downtown Cleveland and University Circle area, 10 minutes to downtown Willoughby and a 5 minute walk to the grocery stores and deli

Top guest favourite

Flat in Chagrin Falls

4.97 out of 5 average rating, 579 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

Guest suite in Shaker Heights

4.84 out of 5 average rating, 175 reviews

Lovely Suite Near Shaker Square & Cleveland Clinic

3rd floor private suite for up to 3 guests in lovely historic home in park-like setting. Near Shaker Square, the Cleveland Clinic, Case, University Hospital, museums, great restaurants, parks with lakes & walking/running trails, & boulevards of lovely mansions. Enjoy original art & fine antiques indoors; guest patio, gardens & soaring trees outside. 15 minutes to downtown Cleveland by nearby public transit or car. Free driveway parking included. Can host ONE quiet dog; NO cats. accepted.

Guest favourite

Flat in Shaker Heights

4.93 out of 5 average rating, 177 reviews

Historic District 2BR on 2nd Floor near CLE Clinic

Get comfy in this 2BR 1Bath historic district charmer 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!

Top guest favourite

Home in Warrensville Heights

4.96 out of 5 average rating, 112 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!

Top guest favourite

Home in Cleveland Heights

4.94 out of 5 average rating, 172 reviews

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.

Guest favourite

Guest suite in Cleveland

4.89 out of 5 average rating, 112 reviews

3 min Drive to Cle Clinic Free Parking

Updated Cozy home, conveniently located three minutes from Cleveland Clinic and University Hospital by car. 16 minute walk to the clinic. Perfect for medical treatment patients/families, healthcare professionals, student Our Century Home has charm combined with modern amenities 5-10 mins from CWRU, Downtown Cleve , Little Italy and Major Sports Venues Home features 55”smart TV (Netflix, Hulu, Disney Plus included), wi-fi, private on site parking, keyless entry, Queen bed

Guest favourite

Cabin in Euclid

4.9 out of 5 average rating, 269 reviews

Century-plus Summer Cabin - The Perfect Getaway!

Cabin.141 is a 120 year old summer cabin that has been added on to & modified more than a few times over the years! Situated in the inner-ring suburb of Euclid, this charming property is just a few houses from Lake Erie and is nestled on a large lot on a quiet street. The home is comfortably furnished with an eclectic mix of antiques & mid-century modern pieces. Beautiful in any season, this property is the ideal spot for a weekend get-away or an extended stay.

Guest favourite

Cabin in Solon

4.87 out of 5 average rating, 172 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!!

Guest favourite

Flat in Maple Heights

5 out of 5 average rating, 6 reviews

Maple Heights Dream

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, free parking, 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!

Top guest favourite

Home in Cleveland

4.98 out of 5 average rating, 214 reviews

Waterloo Gem: Walk to Art & Music

Stay in Cleveland’s vibrant Waterloo Arts District! This newly renovated 2-bedroom home is steps from galleries, local dining, live music, and festivals. Just 15 minutes from downtown, enjoy a bright, comfortable space that captures the neighborhood’s creative energy. Perfect for relaxing or exploring—discover why Cleveland rocks!