Highland Hills holiday rentals

We found 1,002 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Highland Hills to find one that's perfect for your trip. Whether you're staying in a holiday rental with a group or just with your pet, you'll have the amenities that you expect and more, which might include a hot tub and garden. You're sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Highland Hills

Showing deals for:1 Jan - 8 Jan

Queen bed (#1)
I was able to save this amazing front door (with a beveled-oval window)!
A view of the living room from the dining room towards the front door.
Look forward to helping you explore Cleveland.
Exceptional
(61 reviews)

★ Professionally remodeled century home minutes from the clinic & Downtown!

Cleveland Heights

8% off
AU$3,154
for 7 nights, 1 home
AU$451 per night
includes taxes & fees
★ Professionally remodeled century home minutes from the clinic & Downtown!
Room
Private kitchen
Interior
Interior
Exceptional
(7 reviews)

3BR Cozy&Peaceful Retreat +small gym

Cleveland

9% off
AU$2,417
for 7 nights, 1 home
AU$345 per night
includes taxes & fees
3BR Cozy&Peaceful Retreat +small gym
Private kitchen
Living area
Interior
Interior
Very good
(5 reviews)

Modern Little Italy Retreat w/ Balcony & Parking

Cleveland

8% off
AU$2,203
for 7 nights, 1 apartment
AU$315 per night
includes taxes & fees
Modern Little Italy Retreat w/ Balcony & Parking
Interior
Living Room
Interior
Living area
Exceptional
(14 reviews)

Sunscape Bungalow: Close to Hospitals|Quiet Nborhd |Office|WD|Deck

South Euclid

8% off
AU$2,479
for 7 nights, 1 home
AU$354 per night
includes taxes & fees
Sunscape Bungalow: Close to Hospitals|Quiet Nborhd |Office|WD|Deck
Living area
Timeless
Room
Private kitchen
Exceptional
(192 reviews)

Accogliente e caldo #1*Family Run*

Cleveland

22% off
AU$1,868
for 7 nights, 1 apartment
AU$267 per night
includes taxes & fees
Accogliente e caldo #1*Family Run*
Room
Living area
Exterior
Dining
Exceptional
(19 reviews)

Completely Remodeled Exterior And Interior - We're Ready To Host You !

Cleveland Heights

8% off
AU$2,271
for 7 nights, 1 home
AU$324 per night
includes taxes & fees
Completely Remodeled Exterior And Interior - We're Ready To Host You !
Living area
Living area
Interior
Room
Wonderful
(18 reviews)

Cleveland Loft-Wolstein/Progressive/Playhouse/CSU.

Cleveland

12% off
AU$2,103
for 7 nights, 1 apartment
AU$300 per night
includes taxes & fees
Cleveland Loft-Wolstein/Progressive/Playhouse/CSU.
Room
Private kitchen
Living area
Living area
Exceptional
(55 reviews)

Cozy Updated Century Gem- Prime Location - Sleeps 10- Make yourself at home!

Cleveland

8% off
AU$4,358
for 7 nights, 1 home
AU$623 per night
includes taxes & fees
Cozy Updated Century Gem- Prime Location - Sleeps 10- Make yourself at home!
Room
Living area
Living area
Exterior detail
Exceptional
(6 reviews)

Cle Suites 2BR/1BA | 5 min Walk to Cle Clinic #5

Cleveland

8% off
AU$1,853
for 7 nights, 1 apartment
AU$265 per night
includes taxes & fees
Cle Suites 2BR/1BA | 5 min Walk to Cle Clinic #5
Dining
Living area
Interior
Interior
Exceptional
(5 reviews)

Little Italy Gem | King Bed, Gym & Free Parking

Cleveland

8% off
AU$2,203
for 7 nights, 1 apartment
AU$315 per night
includes taxes & fees
Little Italy Gem | King Bed, Gym & Free Parking
Exterior
Private kitchen
Room
Bathroom
Exceptional
(48 reviews)

JUST REMODELED top to bottom - master bed/bath on main floor!

Cleveland Heights

8% off
AU$2,651
for 7 nights, 1 home
AU$379 per night
includes taxes & fees
JUST REMODELED top to bottom - master bed/bath on main floor!
Exterior
Living area
Interior
Living area
Excellent
(22 reviews)

CLE 2BR Loft/Progressive/Playhouse/Wolstein/1 FREE Parking.

Cleveland

12% off
AU$2,225
for 7 nights, 1 apartment
AU$318 per night
includes taxes & fees
CLE 2BR Loft/Progressive/Playhouse/Wolstein/1 FREE Parking.
Exterior detail
Interior
Living area
Property grounds
Exceptional
(6 reviews)

Cle Suites 1BR/1BA | 5 min Walk to Cle Clinic #10

Cleveland

8% off
AU$1,754
for 7 nights, 1 apartment
AU$251 per night
includes taxes & fees
Cle Suites 1BR/1BA | 5 min Walk to Cle Clinic #10
Private kitchen
Living area
Living area
Living area
Exceptional
(10 reviews)

Cle Suites 2BR/1BA | 5 min Walk to Cle Clinic #9

Cleveland

8% off
AU$1,853
for 7 nights, 1 apartment
AU$265 per night
includes taxes & fees
Cle Suites 2BR/1BA | 5 min Walk to Cle Clinic #9

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Highland Hills getaway

Learn about the unique charm of Highland Hills with a stay in a holiday home rental. This city has something for everyone. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Highland Hills

Are you searching for attractions to visit while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Highland Hills a fun place to get away to. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • MGM Northfield Park (6.9 mi / 11.1 km)
  • StoneWater Golf Club (8.3 mi / 13.4 km)
  • Cleveland Metroparks Zoo (10.1 mi / 16.2 km)
  • Greater Cleveland Aquarium (10.2 mi / 16.4 km)
  • Brandywine Ski Resort (11.5 mi / 18.5 km)
  • Boston Mills Ski Resort (12.9 mi / 20.8 km)

Exploring the natural landscape of Highland Hills

Whether you're an outdoor enthusiast or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Highland Hills. These are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Cain Park (4.5 mi / 7.3 km)
  • Cleveland Botanical Garden (6.4 mi / 10.2 km)
  • Cleveland Lakefront State Park (8.5 mi / 13.6 km)
  • Brandywine Falls (9.9 mi / 15.9 km)
  • Cuyahoga River (10 mi / 16.2 km)
  • Edgewater Beach (11.7 mi / 18.9 km)

Transport options to and around Highland Hills

Fly into Cleveland, OH (CGF-Cuyahoga County), the closest airport, located 8.1 mi (13 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Cleveland, OH (BKL-Burke Lakefront), which is 9.6 mi (15.4 km) away.

Frequently asked questions

When is the best time to visit Highland Hills for a holiday rental?
The best time to visit Highland Hills for a holiday rental is during the summer months, particularly in June, when the area comes alive with vibrant energy. This peak season, which runs from June to August, offers visitors a delightful mix of warm weather and a lot of outdoor activities. You can explore the nearby parks, enjoy leisurely walks, and partake in community events that highlight the local culture.June typically enjoys pleasant temperatures ranging from 15 to 30 degrees Celsius, making it an ideal time for sightseeing and outdoor adventures. Whether you're enjoying a picnic in one of the local parks or taking a stroll through the charming neighbourhoods, the climate is great for comfortable exploration.For those looking for more budget-friendly options, consider visiting in February. Although this is a quieter time, it provides a unique opportunity to experience Highland Hills in a more subdued and personal way. You can enjoy the local cafes and explore the area at a leisurely pace, all while benefiting from more affordable rental prices.Ultimately, your choice of when to visit Highland Hills will depend on whether you prefer the bustling atmosphere of summer or the serene charm of winter.
What are the top attractions in Highland Hills?
In Highland Hills, Ohio, visitors can explore a range of attractions that highlight the area's community spirit and natural beauty. One great point of interest is the Highland Hills Community Park, which offers walking paths, sports facilities, and picnic areas, making it an ideal spot for families and outdoor enthusiasts.Additionally, the nearby Shaker Lakes Regional Nature Centre provides opportunities for hiking and birdwatching, allowing guests to immerse themselves in the local flora and fauna. The area is also home to several cultural and historical sites, such as the nearby Shaker Heights Historic District, where visitors can admire well-preserved architecture and learn about the region's rich history.For those interested in shopping and dining, the nearby South Park Mall offers a variety of retail outlets and restaurants, ensuring that visitors have access to essential amenities and leisure activities.
Are all fees included in the Highland Hills holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Highland Hills holiday homes with parking?
Stayz offers a wide selection of holiday homes in Highland Hills with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Highland Hills holiday homes?
You can find great discounts on holiday homes in Highland Hills on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Highland Hills holiday home booking on Stayz?
To find Highland Hills holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Highland Hills?
A long-stay holiday home in Highland Hills is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Highland Hills holiday home?
Book your Highland Hills holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Highland Hills?
Prices for holiday homes in Highland Hills vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Highland Hills to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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