Highland Hills Vacations from $312

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Your Highland Hills Vacation

Say bye-bye to planning hassles and hello to a Highland Hills vacation package. With your travel details organized before you leave, you can focus on discovering every inch of this city, starting with The Flats, which is great for cycling, distilleries and craft breweries and cafes. Eager to explore your new surroundings? Case Western Reserve University, Legacy Village and Pinecrest Plaza Shopping are among the top-rated places to visit during a trip to Highland Hills. Stop daydreaming and start adventuring. Explore the broad range of options on Expedia today and put your Highland Hills vacation plans into action!

The Latest Highland Hills vacation packages

Price found within the past 48 hours. Click for updated prices.
Crowne Plaza Cleveland Airport by IHG

Crowne Plaza Cleveland Airport by IHG

3.5 out of 5
Price was $398, price is now $312 per person
$312
per person
Mar 13 - Mar 16
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
7.2/10 Good! (1,001 reviews)
Yes but we had a wake-up call scheduled for 330 am and we never got a call.. Could have missed our fligjt...

Reviewed on Jan 8, 2026

Holiday Inn Cleveland Clinic by IHG

Holiday Inn Cleveland Clinic by IHG

3 out of 5
Fairfax
Price was $487, price is now $358 per person
$358
per person
Mar 13 - Mar 16
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.8/10 Excellent! (1,231 reviews)
Great. Very good shuttle service to the entire Cleveland clinic hospital campus . Room clean and comfortable and the restaurant has good selection and not overpriced for a hotel restaurant. Absolutely a go to place for the clinic.. but not real cheep but for us it was worth it.

Reviewed on Jan 26, 2026

InterContinental Cleveland by IHG

InterContinental Cleveland by IHG

4.5 out of 5
Fairfax
Price was $551, price is now $432 per person
$432
per person
Mar 13 - Mar 16
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
9/10 Wonderful! (843 reviews)
Nice room, restaurants on site and convenient to Cleveland Clinic! Highly recommended!

Reviewed on Jan 20, 2026

Hotel Indigo Cleveland Downtown by IHG

Hotel Indigo Cleveland Downtown by IHG

3.5 out of 5
Downtown Cleveland
Price was $437, price is now $343 per person
$343
per person
Mar 13 - Mar 16
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.4/10 Very Good! (1,442 reviews)
Clean and great location

Reviewed on Jan 29, 2026

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Discover the most popular places to visit in Highland Hills

The view from the observation deck overlooking downtown Cleveland.

Cleveland Clinic

Though Cleveland Clinic might be what brings you to town, perhaps you'll have a chance to explore more of Cleveland while you are here.

Cleveland Clinic
cleveland skyline

Huntington Bank Field

Catch an event at Huntington Bank Field during your trip to Cleveland. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Huntington Bank Field
Rock and Roll Hall of Fame showing interior views and music

Rock and Roll Hall of Fame

Discover the music and memorabilia from the greatest rock bands in the world and find out why Cleveland is so important to the world of Rock and Roll.

Rock and Roll Hall of Fame

What to do in Highland Hills

Skip the Line: Cleveland History Center Admission Ticket

Skip the Line: Cleveland History Center Admission Ticket

$14
per adult
Skip the Line: Cleveland History Center Admission Ticket
Cleveland Cavaliers Basketball Game at Rocket Mortgage FieldHouse

Cleveland Cavaliers Basketball Game at Rocket Mortgage FieldHouse

$67
per adult
Cleveland Cavaliers Basketball Game at Rocket Mortgage FieldHouse
Cleveland: Eerie Ghosts Haunted Walking Tour

Phantom's Parade on Prospect: Cleveland Ghost Tours

$32
per adult
100% of travellers recommend
Phantom's Parade on Prospect: Cleveland Ghost Tours
See all activities in Highland Hills

Highland Hills Hotel Deals

Hotel Indigo Cleveland Downtown by IHG

Hotel Indigo Cleveland Downtown by IHG

3.5 out of 5
651 Huron Rd E Cleveland OH
Fully refundable
$88 nightly
The price is $104 total per night from Feb 16 to Feb 17
$104 total
Feb 16 - Feb 17
Total with taxes and fees
8.4/10 Very Good! (1,540 reviews)
Very clean. Very close to cavs and casino.

Reviewed on Jan 27, 2026

Hotel Indigo Cleveland Downtown by IHG
Hyatt Regency Cleveland At The Arcade

Hyatt Regency Cleveland At The Arcade

4 out of 5
420 Superior Ave E Cleveland OH
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $140 total per night from Feb 22 to Feb 23
$140 total
Feb 22 - Feb 23
Total with taxes and fees
8.8/10 Excellent! (1,115 reviews)
Everything was great the staff and valet parking was great

Reviewed on Jan 30, 2026

Hyatt Regency Cleveland At The Arcade
The Westin Cleveland Downtown

The Westin Cleveland Downtown

4 out of 5
777 Saint Clair Ave Ne Cleveland OH
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $128 total per night from Feb 1 to Feb 2
$128 total
Feb 1 - Feb 2
Total with taxes and fees
8.6/10 Excellent! (2,032 reviews)
Room was very clean. Staff were very nice.

Reviewed on Jan 30, 2026

The Westin Cleveland Downtown
See all 1,944 properties in Highland Hills
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.

Find the Best Highland Hills Vacation Packages

Highland Hills Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Hopkins Intl. Airport (CLE)
Population
960
Top Sights
The Temple Tifereth Israel, Pinecrest Plaza Shopping and ETON Chagrin Blvd Shopping Center

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Frequently asked questions

How much does a Highland Hills vacation package cost?
You can grab a vacation package to this destination from $312 on Expedia. However, how much your vacation to Highland Hills costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Highland Hills?
You can usually find lower rates and better availability in December, January and February. Browse our cheap Highland Hills vacation packages and you could score some great off-season deals.
How many days is enough for Highland Hills?
Usually, a handful of days is enough to see the major sights during your Highland Hills vacation. However, if you'd like to have more time to chill out or go on day tours, consider extending your trip.
How to find the best Highland Hills package deals?
Use Expedia's filter tool to help you find some unbeatable Highland Hills package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Highland Hills package deals in the off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Highland Hills vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll typically score a better deal than booking each component separately. And you'll still enjoy the flexibility to create a customized Highland Hills vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Highland Hills?
If you have your Highland Hills travel dates locked in, book early to score some incredible deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Highland Hills?

  1. Choose when to go: Check your schedule and get packing. Your favorite season and the type of activities on offer will also help you decide when to vacation in Highland Hills.
  2. Plan your budget wisely: On top of the cost of your accommodations, you'll need to consider other expenses. These include flights, transportation and food. Also, put aside some extra funds for unexpected costs that may crop up during your trip to Highland Hills.
  3. Explore Highland Hills using our trip planning tool: Gain insights into the leading attractions and best properties for your trip to Highland Hills. You can also save your must-visit places, collaborate with friends and family and organize all your plans in one place.
  4. Decide how long to go for: Now that you know more about Highland Hills, you can work out the right length of your vacation. Put together a rough plan and allocate enough time to cover everything you want to do.
  5. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a tailored Highland Hills vacation package.
  6. Book experiences or activities in advance: Whether it's a ticket to a big attraction or a day trip, you won't have to worry about missing out on Highland Hills's best offerings. Find all the exciting things to do in Highland Hills with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Highland Hills vacation packages?
Jet off on your ideal getaway to Highland Hills with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or wait until your next payday — we've teamed up with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans mean you can spread the cost over 3, 6 or 12 months. With no late payment fees or extra charges, you can easily stick to your budget and snap up travel deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.