Default HTG hotel image

Highland Hills Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Highland Hills vacation rentals

Exterior detail

1. Lovely near Cleve Clinic/CWRU/UH - in Larchmere w/Porch!

Lovely near Cleve Clinic/CWRU/UH - in Larchmere w/Porch!
Buckeye-Shaker
9.4 out of 10, Exceptional, (102 reviews)
"This was a great choice for our trip to Cleveland. Communication was great, check in and out was easy, quiet area and no issues with parking! It was definitely perfect for our stay!"
United States
Amber D.
Lovely near Cleve Clinic/CWRU/UH - in Larchmere w/Porch!
A two-story house with a porch, a small front yard, and a visible front door.

2. 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.
$226 nightly
The price is $239
Oct 4 - Oct 5
Total with taxes and fees
Walk to Dining, Bars & Transit!
A living room with a sofa, a coffee table, a fireplace, and artwork on the wall.

3. 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.
$200 nightly
The price is $200
Oct 5 - Oct 6
Total with taxes and fees
The Gallery House - Art curated by local artist!
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
$214 nightly
The price is $214
Oct 5 - Oct 6
Total with taxes and fees
Classic Meets Contemporary I Minutes to Cle Clinic
A modern living room with a flat-screen TV mounted on a wall, a wooden entertainment center, and a zebra-patterned rug.

5. 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
$160 nightly
The price is $162
Sep 30 - Oct 1
Total with taxes and fees
Chic Coventry — Enjoy 10% off 2+ Nights +Late Check Out
A bedroom with a bed, a bedside table, a wall-mounted TV, and a window with curtains.

6. Hilliard Lofts

Hilliard Lofts
2.0 star property
Downtown Cleveland
$225 nightly
The price is $264
Oct 4 - Oct 5
Total with taxes and fees
Hilliard Lofts
An outdoor hot tub area with stone flooring, a brick wall, and string lights.

7. 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.
$204 nightly
The price is $220
Oct 4 - Oct 5
Total with taxes and fees
Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!
A modern kitchen with a large island, wooden cabinets, and a large window.

8. Historic Cleveland Heights Carriage House!

Historic Cleveland Heights Carriage House!
Cleveland Heights
9.6 out of 10, Exceptional, (58 reviews)
"Close to the Clinic, easy to walk to shops and eateries and walk/run. Very communicative host and this is my second stay!"
United States
Mary A.
$347 nightly
The price is $391
Sep 30 - Oct 1
Total with taxes and fees
Historic Cleveland Heights Carriage House!
A modern kitchen with dark cabinetry, a black countertop, and a coffee maker.

9. 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, (82 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.
$186 nightly
The price is $196
Oct 20 - Oct 21
Total with taxes and fees
Large duplex king size bed and two queen size
A modern living room with a blue sofa, a coffee table, and a kitchen area with a bar and stools.

10. 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.
$195 nightly
The price is $211
Sep 30 - Oct 1
Total with taxes and fees
Upscale Little Italy 2BR | Private Drive & Patio
An outdoor hot tub area with stone flooring, a brick wall, and string lights.

11. 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.
$204 nightly
The price is $215
Oct 6 - Oct 7
Total with taxes and fees
Rare Cleveland Apt: Heart of Little Italy! With Sauna & Hot Tub!
A modern kitchen with a central island, bar stools, stainless steel appliances, and pendant lighting.

12. 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, (57 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.
$289 nightly
The price is $305
Oct 14 - Oct 15
Total with taxes and fees
Little Italy! Close to Cleveland Clinic, University Hospital & University Circle
A modern bedroom with a loft bed, a sofa, and a coffee table.

13. 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
$205 nightly
The price is $222
Oct 19 - Oct 20
Total with taxes and fees
Modern Victorian Studio -Steps to Cleveland Clinic
A modern building with large windows, a balcony with wicker furniture, and a view of greenery.

14. Gorgeous 2 Bed/2 Bath | CLE Clinic | Balcony

Gorgeous 2 Bed/2 Bath | CLE Clinic | Balcony
Hough
8.8 out of 10, Excellent, (13 reviews)
"It was the perfect location to be with my family member having surgery at The Cleveland Clinic. Very clean, safe, and home away from home during a stressful time for my family. Would highly recommend!"
United States
Melissa
$269 nightly
The price is $292
Oct 4 - Oct 5
Total with taxes and fees
Gorgeous 2 Bed/2 Bath | CLE Clinic | Balcony
A modern kitchen with a large island, a dining area with a table and chairs, and large windows offering a city view.

15. Modern & Elegant 2BR | Cleveland Clinic

Modern & Elegant 2BR | Cleveland Clinic
University Circle
10.0 out of 10, Exceptional, (18 reviews)
"Great location and new property"
United States
Vidya
$317 nightly
The price is $344
Oct 18 - Oct 19
Total with taxes and fees
Modern & Elegant 2BR | Cleveland Clinic
An outdoor hot tub area with stone flooring, a brick wall, and string lights.

16. Cleveland Rocks-Little Italy! Massage chair/Hot tub #3

Cleveland Rocks-Little Italy! Massage chair/Hot tub #3
University Circle
10.0 out of 10, Exceptional, (25 reviews)
"Nice, roomy, clean."
United States
Mike J.
$246 nightly
The price is $260
Oct 5 - Oct 6
Total with taxes and fees
Cleveland Rocks-Little Italy! Massage chair/Hot tub #3
A living room with a blue sofa, a wooden coffee table, and a ceiling fan.

17. Center of Little Italy #1

Center of Little Italy #1
University Circle
9.4 out of 10, Exceptional, (21 reviews)
"Great stay and great location!"
United States
Katlyn A.
$226 nightly
The price is $245
Oct 20 - Oct 21
Total with taxes and fees
Center of Little Italy #1
A modern living room with a sofa, coffee table, and TV.

18. Nice Apartment next to Christmas Story House

Nice Apartment next to Christmas Story House
Tremont
9.4 out of 10, Exceptional, (30 reviews)
"We absolutely loved this place ! "
United States
Celeste K.
$150 nightly
The price is $155
Sep 30 - Oct 1
Total with taxes and fees
Nice Apartment next to Christmas Story House
A hot tub in a wooden deck area with a wooden fence and a pergola overhead.

19. Lovely 2 Bedroom Unit with a Hot Tub

Lovely 2 Bedroom Unit with a Hot Tub
Tremont
9.6 out of 10, Exceptional, (92 reviews)
"it was great"
United States
Taleah A.
$193 nightly
The price is $205
Sep 30 - Oct 1
Total with taxes and fees
Lovely 2 Bedroom Unit with a Hot Tub
A living room with a sofa, a coffee table, a TV, and a foosball table.

20. 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, (11 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
$220 nightly
The price is $220
Oct 11 - Oct 12
Total with taxes and fees
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Highland Hills Hotel Reviews

Crowne Plaza Cleveland at Playhouse Square by IHG

Crowne Plaza Cleveland at Playhouse Square by IHG

10/10 Excellent
"Super friendly staff in hotel and restaurant. Very accessible to all the theatres in Playhouse Square. We are returning to Cleveland next month and will stay here again!"
Kathleen 4-night trip
Posted 1 hour ago
Crowne Plaza Cleveland at Playhouse Square by IHG

Find out more about Highland Hills

Everything you need to know about Highland Hills vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Highland Hills vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Highland Hills vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Highland Hills vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Highland Hills. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Highland Hills in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $114 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Highland Hills rentals

At Expedia, we put the best Highland Hills vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Highland Hills rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Highland Hills vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Highland Hills. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Highland Hills?

Yes, we give you a choice of vacation rentals close to popular local attractions in Highland Hills, or you can select a secluded option if you're looking for a relaxing stay.

What's the top vacation rental in Highland Hills?

Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch: This vacation home rental near 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 vacation with amenities like 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 larger area, you’ll find Thistledown Racetrack and Pinecrest Plaza Shopping.

What are vacation rentals like in Highland Hills?

Vacation rentals are private properties you can reserve for several days or more in Highland Hills. Vacation rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive choice for a family getaway.