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.

%{current} / %{total}1 / 1
Top Guest favourite
A spacious living area is furnished with a gray sofa, yellow accent chairs, and a mid-century modern coffee table. A large television is mounted on a stylish console. Natural light enters through large windows, complementing the neutral color scheme and patterned area rug, enhancing the cozy ambiance.
Apartment in Shaker Heights
4.94 out of 5 average rating, 163 reviews

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!

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, 620 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.

Top Guest favourite
A spacious deck offers a panoramic view of Lake Erie, with sunlight reflecting on the water. Two chairs surround a simple table, inviting relaxation. The deck is bordered by vibrant greenery, and a warm glow is cast over the scene by the setting sun.
Cottage in Willowick
4.97 out of 5 average rating, 326 reviews

Lake House with Amazing Views

Amazing location right on Lake Erie. This cozy lake house has a large kitchen, full bathroom and a living room/bedroom with king-size bed. The cottage is off by itself so you can enjoy your seclusion, but we live about 200 feet away so we can assist you if you need us. Enjoy a morning coffee on the deck while watching nature, spectacular sunsets on the private patio, and falling asleep to the sounds of the lake. You will be blown away by the beauty and peacefulness of this amazing cottage.

Top 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
5 out of 5 average rating, 123 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.

Guest favourite
A spacious living room features a light-colored sofa paired with a textured area rug. A coffee table holds a small plant and a remote. Natural light filters through sheer curtains over a 50" Flatscreen TV, illuminating the inviting space.
Apartment in Shaker Heights
4.91 out of 5 average rating, 217 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
A bright living area features a spacious sofa adorned with patterned cushions, complemented by an area rug with intricate designs. Large windows allow natural light to fill the space, while a decorative table and various accent lamps add warmth and charm. French doors provide access to the outdoor patio.
Home in Cleveland Heights
4.95 out of 5 average rating, 205 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.

Top Guest favourite
Home in Warrensville Heights
4.97 out of 5 average rating, 133 reviews

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

Top Guest favourite
Brandywine Falls is viewed through a canopy of autumn foliage, featuring vibrant orange and gold leaves. A wooden observation platform allows visitors to admire the cascading water and lush scenery, creating a serene natural setting in the Cuyahoga Valley National Park.
Apartment in Northfield
4.97 out of 5 average rating, 379 reviews

Brandywine Falls Hike, Bike & Relaxation Suite

Private comfortable suite in the beautiful Cuyahoga Valley National Park. Mid-way between Cleve. & Akron. Adjacent to miles of paved walk/bike trails. Bring your bike or use rentals nearby. Visit historic villages of Hudson & Peninsula. Fine dining. Quiet Country estate setting. 5 minute walk to spectacular Brandywine Falls or rest your feet on the ottoman. Spring, Summer and Fall foliage is stunning. Among Ohios most beautiful sight seeing areas.

Guest favourite
A log cabin nestled among trees is framed by a gravel pathway leading to the entrance. Large stones outline the front area, while surrounding greenery creates a sense of seclusion. Sunlight filters through the leaves, creating a serene and inviting atmosphere.
Cabin in Solon
4.87 out of 5 average rating, 199 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
The entrance features a teal awning above a green door with glass panels. Potted plants with colorful flowers are displayed on either side, enhancing the welcoming appearance. A mailbox is positioned next to the door, contributing to the functional design.
Apartment in Bedford
4.91 out of 5 average rating, 234 reviews

Quaint 1 BR Apt Above Bicycle Shop

Quiet and cozy one bedroom apartment in a historic downtown Bedford building. It is ideal for a comfortable get away that is readily accessible to the major highways in the greater Cleveland area and is easy to get to The Cuyahoga County National Park, Cleveland Metroparks and local Hospital campuses. We are located directly above a bicycle shop near several restaurants, bars and grills, coffee shops, and unique shops.

Guest favourite
A dining area is visible, featuring a round glass table surrounded by four upholstered chairs. A modern chandelier is suspended above the table. The living space includes a light-colored sofa, and soft lighting enhances the serene atmosphere.
Home in Warrensville Heights
4.91 out of 5 average rating, 107 reviews

Remodeled, Bright Three Bedroom Home

This peaceful home is located in a quiet neighborhood that is minutes from highways, shopping and restaurants! Enjoy relaxing in the living room, cooking up a tasty meal in the large kitchen, or getting some work done in the dedicated work space. This spacious, bright space is guaranteed to make you feel right at home!

Top Guest favourite
A charming brick home is seen from the front, featuring large windows accented by black shutters. A vibrant tree with red and orange leaves stands prominently in the front yard, contrasting with the green grass and the dark awning over the entrance.
Home in Cleveland Heights
4.96 out of 5 average rating, 181 reviews

Fabulous Fairmount Retreat

Enjoy a charming, sunny home located in the heart of The Heights across from an acclaimed French bakery and buzzing Parisian style bistro. Walk to shops or the Shaker Lakes. Perfect spot for visits with family, or access to local universities, the Cleveland Clinic or University Circle museums and cultural institutions.

Popular amenities for Highland Hills holiday rentals

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