Holiday houses in Highland Hills

5 out of 5 average rating, 26 reviews

Guest suite in Hudson

Hudson Hideaway

Welcome to our cozy suite in charming Hudson, OH – an idyllic retreat perfect for couples or solo travelers looking for a private, peaceful escape. This intimate space combines comfort, style and relaxation with touches of luxury to make your stay unforgettable. Private patio and screened porch/entryway, two-person infrared sauna, fireplace, two Roku TVs and fully equipped kitchen with complimentary coffee bar. Minutes from downtown Hudson, Cuyahoga Valley National Park and Blossom Music Center.

4.94 out of 5 average rating, 157 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!

4.89 out of 5 average rating, 46 reviews

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.

4.92 out of 5 average rating, 116 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!

Apartment in Chagrin Falls

4.97 out of 5 average rating, 572 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.

4.99 out of 5 average rating, 428 reviews

Home in Garrettsville

“Willow Ledge at Silver Creek”with Private Hot Tub

New Construction Modern Ranch House features rustic upscale design with beautiful cozy interiors and comfort at every turn. Stunning views await with floor to ceiling windows overlooking beautiful Silver Creek and surrounding nature. Private deck is spacious and inviting with oversize hot tub, concrete fire pit, gas grill, and outdoor dining furniture. A few minutes from great restaurants, the Brewery at Garrett’s Mill, and the coolest Coffee Shop. Perfect weekend getaway or business stay.

Guesthouse in University Heights

4.98 out of 5 average rating, 285 reviews

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.

5 out of 5 average rating, 16 reviews

Upscale 2Br Near Van Aken/Hospital/CWRU (2nd FL)

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.

Apartment in Cleveland Heights

4.92 out of 5 average rating, 26 reviews

Contemporary Cedar-Lee Walkup

Bright, light, and open layout with contemporary style set in a charming turn of the century retail building. This walk-up apartment features open kitchen, dinning and living area. Newly restored to highlight the 1920s charm with original hardwood floors and brass fixtures. Located directly above a commercial storefront, enjoy a quiet and comfortable stay that is convenient to the dining options of Cedar-Lee as well as Cleveland Clinic, University Hospitals, and Downtown Cleveland.

Guest suite in Cleveland Heights

4.96 out of 5 average rating, 471 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.

Home in Warrensville Heights

4.96 out of 5 average rating, 104 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!

Apartment in Cleveland Heights

5 out of 5 average rating, 61 reviews

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.

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Other great holiday rentals in Highland Hills

Private room in Cleveland Heights

4.96 out of 5 average rating, 148 reviews

A room that is home away from home

MaxRating, 5 stars1 day ago

The home was lovely, tucked away in a residential, tree-lined street. The room was exactly as depicted, standard but comfortable and private. Both hosts were friendly and approachable. There are a bunch of restaurants and cafes <10 mins away on foot and the area is connected by buses to get around. I would book it again gladly.

Condo in Warrensville Heights

4.63 out of 5 average rating, 125 reviews

Lovely 3-bedroom condo with free parking

KenniRating, 5 stars3 weeks ago

The home was clean, quaint, and cozy. I was glad the place was mostly carpeted, as it was pretty cold during our stay. The beds that we did use for sleep were comfortable and the bathroom was clean. Kitchen had a lot more appliances than I expected, although we only used the toaster. Considering most of the stay we were out, it was nice to use the large TV in the living room for gaming at night, and the WiFi was good too. The neighborhood was quiet for the most part, each neighbor kinda doing their own thing. Overall, I’d give our stay a 8.9/10. I’ll definitely consider this place for my top option when I return next year.

Private room in Cleveland Heights

4.91 out of 5 average rating, 106 reviews

Home away from home 5

ShonnieceRating, 5 stars3 weeks ago

Sladjana was a phenomenal host! Very quiet pleasant stay for my commute assignment. Lots of amenities in walking distance. Would definitely pick her stay if I have another commute near by ⭐️ ⭐️ ⭐️ ⭐️ ⭐️

Private room in Beachwood

4.72 out of 5 average rating, 61 reviews

Beautiful Beachwood Home on Green

MaxRating, 5 stars5 months ago

Katerina was a kind and gracious host

Private room in South Euclid

4.95 out of 5 average rating, 164 reviews

Brick Bungalow/Upstairs Bedroom

ShannonRating, 5 stars6 days ago

Michelle was great and super friendly. The space was clean and easily accessible. Perfect for my stay.

4.94 out of 5 average rating, 17 reviews

Private room in Bedford

Abbi’s Haven - Short term Stay Unit 1

MamukaRating, 5 stars8 months ago

Friendly and responsive host with a clean, comfortable home. Located in a pleasant area and the small-town setting makes it easy to walk everywhere. Great value for the price.

Private room in Cleveland Heights

4.88 out of 5 average rating, 264 reviews

Private 3rd floor suite with full bath

DavidRating, 5 stars5 days ago

David's place was perfect for my trip. It was just a short walk from the bus route and a do able amount from the train. After a day outside, the air conditioning chilled and refreshed me before my evening. His space was very thoughtful (coffee included) and cozy, too. It gave me an opportunity to recharge before attending my concert in town, which wasn't that far. The neighborhood was great and I would absolutely stay there again. Thanks a lot.