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Highland Hills Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Highland Hills holiday rentals

A living room with a sofa, a coffee table, a fireplace, and artwork on the wall.

1. The Gallery House - Art curated by local artist!

The Gallery House - Art curated by local artist!
Cleveland Heights
9.6 out of 10, Exceptional, (9 reviews)
"Everything was great. I will be back!"
United States
David T.
The price is HK$683
HK$1,766 total
includes taxes & fees
6 Oct - 7 Oct
The Gallery House - Art curated by local artist!
A modern living room with a flat-screen TV mounted on a wall, a wooden entertainment center, and a zebra-patterned rug.

2. Chic Coventry — Enjoy 10% off 2+ Nights +Late Check Out

Chic Coventry — Enjoy 10% off 2+ Nights +Late Check Out
Cleveland Heights
9.0 out of 10, Wonderful, (27 reviews)
"Excellent walkable location. Good for one night in town for an event."
United States
Whitney
The price is HK$549
HK$1,272 total
includes taxes & fees
6 Oct - 7 Oct
Chic Coventry — Enjoy 10% off 2+ Nights +Late Check Out
A bedroom with a bed, two windows with curtains, a flat-screen TV on the wall, and a waste bin.

3. Hilliard Lofts

Hilliard Lofts
2.0 star property
Downtown Cleveland
6.0 out of 10, (1 review)
"The bed sheets are terrible, there's white stuff material coming out from the bed sheets and sticks all over your clothes. A very weird smell in the the room and hallway. Windows are paper thin that you can hear people outside having conversations from the second floor. Price and location was great and the fact that it had a fridge and stove top with microwave was great too."
United States
mario
The price is HK$1,177
HK$2,075 total
includes taxes & fees
6 Oct - 7 Oct
Hilliard Lofts
A dining area with a dark wooden table, four chairs, and a decorative centerpiece.

4. Classic Meets Contemporary I Minutes to Cle Clinic

Classic Meets Contemporary I Minutes to Cle Clinic
Cleveland Heights
9.6 out of 10, Exceptional, (14 reviews)
"House was very clean and cozy. Great location."
United States
Monica
The price is HK$596
HK$1,562 total
includes taxes & fees
25 Oct - 26 Oct
Classic Meets Contemporary I Minutes to Cle Clinic
A two-story house with a porch, a small front yard, and a visible front door.

5. Walk to Dining, Bars & Transit!

Walk to Dining, Bars & Transit!
Union-Miles Park
8.4 out of 10, Very good, (146 reviews)
"We came for my son’s graduation and had a great time. The location was centralized to everything we wanted to do. We would stay again."
United States
Chrissy W.
The price is HK$581
HK$1,891 total
includes taxes & fees
12 Oct - 13 Oct
Walk to Dining, Bars & Transit!
A modern bedroom with a loft bed, a sofa, and a coffee table.

6. Modern Victorian Studio -Steps to Cleveland Clinic

Modern Victorian Studio -Steps to Cleveland Clinic
Hough
10.0 out of 10, Exceptional, (18 reviews)
"Great location near Cleveland Clinic. Very clean room with free parking onsite."
United States
Mike
The price is HK$667
HK$1,743 total
includes taxes & fees
20 Oct - 21 Oct
Modern Victorian Studio -Steps to Cleveland Clinic
A modern living room with a blue sofa, a coffee table, and a kitchen area with a bar and stools.

7. Upscale Little Italy 2BR | Private Drive & Patio

Upscale Little Italy 2BR | Private Drive & Patio
University Circle
9.4 out of 10, Exceptional, (12 reviews)
"Great location"
United States
Sandra S.
The price is HK$620
HK$1,837 total
includes taxes & fees
11 Oct - 12 Oct
Upscale Little Italy 2BR | Private Drive & Patio
A dining area with a dark wooden table and chairs, a chandelier, and a kitchen in the background.

8. Next 2 Christmas Story House/Tremont/5min downtown

Next 2 Christmas Story House/Tremont/5min downtown
Tremont
9.6 out of 10, Exceptional, (98 reviews)
"Host was great"
United States
Jennifer E.
The price is HK$463
HK$1,211 total
includes taxes & fees
19 Oct - 20 Oct
Next 2 Christmas Story House/Tremont/5min downtown
An outdoor hot tub area with stone flooring, a brick wall, and string lights.

9. Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!

Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!
University Circle
10.0 out of 10, Exceptional, (89 reviews)
"Great location. Great host."
United States
Mike B.
The price is HK$973
HK$1,735 total
includes taxes & fees
7 Oct - 8 Oct
Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!
A sign for Cleveland Metroparks at Edgewater Beach.

10. CAL KING BED, FREE PARKING PASS FOR 1 CAR, BY DOWNTOWN & CLINIC

CAL KING BED, FREE PARKING PASS FOR 1 CAR, BY DOWNTOWN & CLINIC
Goodrich-Kirtland Park
8.6 out of 10, Excellent, (55 reviews)
"Everything as described! Great stay!"
United States
Billy M.
The price is HK$455
HK$1,083 total
includes taxes & fees
26 Oct - 27 Oct
CAL KING BED, FREE PARKING PASS FOR 1 CAR, BY DOWNTOWN & CLINIC
A modern kitchen with dark cabinetry, a black countertop, and a coffee maker.

11. Large duplex king size bed and two queen size

Large duplex king size bed and two queen size
Cleveland Heights
9.0 out of 10, Wonderful, (83 reviews)
"The place was great, awesome, close to everything we needed. Thank you for a great place to stay. Plenty of room and bathrooms."
United States
Michelle T.
The price is HK$965
HK$1,516 total
includes taxes & fees
13 Oct - 14 Oct
Large duplex king size bed and two queen size
A modern kitchen with a central island, stainless steel appliances, pendant lighting, and a wooden floor.

12. Charming studio apartment in fantastic Cleveland Tremont area

Charming studio apartment in fantastic Cleveland Tremont area
Tremont
7.8 out of 10, Good, (42 reviews)
"This is a great apartment for a quick trip."
United States
Kristin
The price is HK$466
HK$1,086 total
includes taxes & fees
6 Oct - 7 Oct
Charming studio apartment in fantastic Cleveland Tremont area
A Roku TV on a wooden TV stand with a potted plant beside it.

13. Cozy 1bed 1bath near Airport, Cleveland Clinic, & Downtown CLE

Cozy 1bed 1bath near Airport, Cleveland Clinic, & Downtown CLE
Clark-Fulton
9.4 out of 10, Exceptional, (6 reviews)
"Place looks a lot better in photos than in actuality but all in all WAY better than any hotel. The parking situation is a bit dicey though and the door to the bathroom can use an upgrade."
United States
Mohammad B.
The price is HK$918
HK$1,075 total
includes taxes & fees
7 Oct - 8 Oct
Cozy 1bed 1bath near Airport, Cleveland Clinic, & Downtown CLE
An outdoor hot tub area with stone flooring, a brick wall, and string lights.

14. Rare Cleveland Apt: Heart of Little Italy! With Sauna & Hot Tub!

Rare Cleveland Apt: Heart of Little Italy! With Sauna & Hot Tub!
University Circle
10.0 out of 10, Exceptional, (72 reviews)
"Awesome place!!"
United States
Quintin B.
The price is HK$973
HK$1,696 total
includes taxes & fees
6 Oct - 7 Oct
Rare Cleveland Apt: Heart of Little Italy! With Sauna & Hot Tub!
A modern living room with a grey sectional sofa, a red chair, a round wooden coffee table, a TV stand, and a large window with a city view.

15. Cleveland Loft-Wolstein/Progressive/Playhouse/CSU.

Cleveland Loft-Wolstein/Progressive/Playhouse/CSU.
Downtown Cleveland
9.2 out of 10, Wonderful, (20 reviews)
"Great stay would recommend to anyone"
United States
Shane S.
The price is HK$417
HK$1,384 total
includes taxes & fees
7 Oct - 8 Oct
Cleveland Loft-Wolstein/Progressive/Playhouse/CSU.
A modern kitchen with a central island, bar stools, stainless steel appliances, and pendant lighting.

16. Little Italy! Close to Cleveland Clinic, University Hospital & University Circle

Little Italy! Close to Cleveland Clinic, University Hospital & University Circle
University Circle
10.0 out of 10, Exceptional, (58 reviews)
"This is easily the best place I’ve stayed. Debbie thinks of everything. This was my second time here and looking forward to number 3!"
United States
Connie H.
The price is HK$1,020
HK$2,166 total
includes taxes & fees
7 Oct - 8 Oct
Little Italy! Close to Cleveland Clinic, University Hospital & University Circle
A bright kitchen with white cabinets, a wooden dining table, and chairs.

17. Luxury Downtown Townhome w/ Private Garage Unit 4

Luxury Downtown Townhome w/ Private Garage Unit 4
Downtown Cleveland
9.8 out of 10, Exceptional, (79 reviews)
"Was a wonderful stay. Great location and very clean!"
United States
Joanna R.
The price is HK$392
HK$1,354 total
includes taxes & fees
13 Oct - 14 Oct
Luxury Downtown Townhome w/ Private Garage Unit 4
A covered patio area with wooden beams, a swing chair, and several plastic chairs.

18. Gordon Square Studio ~ 4 Mi to Downtown Cleveland!

Gordon Square Studio ~ 4 Mi to Downtown Cleveland!
3.0 star property
Detroit - Shoreway
8.8 out of 10, Excellent, (8 reviews)
"Lovely stay - comfortable studio, communicative host, great location, and easy parking. "
United States
Rachel
The price is HK$644
HK$1,283 total
includes taxes & fees
8 Oct - 9 Oct
Gordon Square Studio ~ 4 Mi to Downtown Cleveland!
A living room with a sofa, a coffee table, a TV, and a foosball table.

19. Heart of Little Italy- Walk to CWRU & Cleveland Clinic -Free Parking

Heart of Little Italy- Walk to CWRU & Cleveland Clinic -Free Parking
University Circle
9.2 out of 10, Wonderful, (12 reviews)
"I ran into one little hiccup and the host was very responsive and took care of it right away. I would highly recommend this location for its walkability to local sites."
United States
Jaymie
The price is HK$876
HK$1,700 total
includes taxes & fees
12 Oct - 13 Oct
Heart of Little Italy- Walk to CWRU & Cleveland Clinic -Free Parking
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Highland Hills Hotel Reviews

Drury Plaza Hotel Cleveland Downtown

Drury Plaza Hotel Cleveland Downtown

10/10 Excellent
"The location was great. Loved their amenities."
Diana 2-night trip
Posted less than an hour ago
Drury Plaza Hotel Cleveland Downtown

Find out more about Highland Hills

Search for holiday rentals in Highland Hills on Expedia! You can easily find your home rentals, villas, holiday apartments in Highland Hills using one of the methods below:

  • View our selection of featured holiday rentals in Highland Hills
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  • Enter your travel dates to view the best deals on holiday rentals in Highland Hills while they last

Look no further and take a look at our great range of rental properties in Highland Hills!

Frequently asked questions

Are there holiday rentals in Highland Hills?

Yes, there are holiday rentals close to the most popular sights in Highland Hills, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Highland Hills has to offer?

Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch: This holiday home rental outside of Highland Hills offers a balcony, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What can I see and do in Highland Hills?

Explore the area and family-friendly sights such as Cleveland Museum of Natural History, or get out into nature at a spot like Cleveland Botanical Garden. In the wider area, you’ll find Thistledown Racetrack and Pinecrest Plaza Shopping.

What are holiday rentals like in Highland Hills?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Highland Hills. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for family trips.