Holiday rentals in Highland Hills

Shaker Heights Suite Near Cleveland Clinic

3rd floor private suite for up to 3 guests in lovely historic Shaker Heights 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 dog; NO cats accepted.

Charming Cleveland Getaway with Premier Hosting

A Cozy Stay in Cleveland – Private First-Floor Unit of a Quiet Duplex Welcome to your comfortable home base in Cleveland! This listing is for the private first floor of a charming and quiet duplex. The upstairs unit is currently unoccupied, offering you an extra layer of peace and privacy during your stay. Inside, you’ll find a thoughtfully styled space with inviting bedrooms, a fully equipped kitchen, and a calming three-season porch—perfect for morning coffee or winding down in the evening.

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.

Tyndall Carriage House-Private Guesthouse

Tyndall Carriage House is a cozy, private, secluded guesthouse in a separate building behind our home. The carriage house has a private entrance, a small kitchen and bathroom on the first level, the living area and bedroom are upstairs above our garages. Perfect for a weekend getaway or longer stays. Located in University Heights, a friendly, safe, walk/bike-able neighborhood, close to John Carroll University, minutes from downtown Cleveland, the Cleveland Clinic and other city attractions.

Upscale 2Br in Van Aken Near Hospital/University

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.

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.

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!

New! “Modernistic Retreat”

Elevate your stay in this bright, elegant and spacious 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.