Holiday houses in Highland Hills

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 short 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, in a safe/historic neighborhood. Apartment is located on a 3rd floor of a Tudor house, some stairs are required to access.

Modern Farmhouse Chagrin Falls Beachwood CVNP

Private Custom-Renovated Modern Farmhouse tucked into a wooded setting minutes from downtown Chagrin Falls and Hunting Valley. Neighboring Beachwood, Moreland Hills & Pepper Pike. 20min to Cuyahoga Valley National Park. Heated slate floors, spa like bath with endless hot water, dual work spaces & true privacy. Affectionately dubbed “The Wayback,” this home sleeps 6 with 2 private bedrooms, a fully equipped kitchen, and upscale amenities near Pinecrest & ETON dining, shopping, and entertainment.

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.

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!

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.

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.

Cle Heights Nature’s Getaway | 2bed1bath | AC Pets

~ Thoughtfully designed space with modern touches ~ Comfortable bedrooms for a restful night’s sleep ~ Fully equipped kitchen for cooking and dining ~ Cozy living area perfect for relaxing ~ Fast WiFi + Smart TV ~ Free parking included ~ Ideal for short or extended stays Conveniently located near: • Cleveland Clinic • University Circle & Case Western • Restaurants, cafes, and nightlife • Downtown Cleveland (quick drive) Enjoy the spacious backyard and frequent deer guests!

Rare Cleveland Apt: Little Italy! W/Sauna&Hot tub!

Fall in love with this charming, newly updated 1-bedroom, 1-bath lower unit triplex apartment situated in the heart of Little Italy, walking distance from University Circle, UH Hospital, Cleveland Museum of Art, Botanical Garden, Public Transportation and much more. Apartment is complete with a well-equipped kitchen, Smart TV, laptop workspace, and modern furnishings, this vacation/business rental delivers all the essentials so you can spend more time relaxing and exploring.

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 on.

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

Clean and Cozy Carriage House Getaway

Sunny and cozy carriage house in safe, historic neighborhood - perfectly appointed for overnight guests or extended stay visitors. Close proximity to Cleveland Clinic, Case Western, John Carroll University, Shaker Lakes & University Circle. Enjoy the charm of staying in this premier neighborhood with the comforts of home including updated kitchen, furnishings, bed/bedding and spa shower. Beautiful, safe, tree-lined street with private entrance and parking spot.

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!!