Highland Hills Vacations from $498

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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.
DoubleTree by Hilton Hotel Cleveland Downtown - Lakeside

DoubleTree by Hilton Hotel Cleveland Downtown - Lakeside

4 out of 5
Downtown Cleveland
Save 100% on your flight
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
7.2/10 Good! (1,263 reviews)
The staff at the desk, especially the Ashleys, and Lexus, were super nice. The bar staff was awesome too.

Reviewed on Aug 11, 2025

The Willoughby House

The Willoughby House

3 out of 5
Save 100% on your flight
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
10/10 Exceptional! (2 reviews)
Beautiful property. Nice location. Excellent lounge & restaurant.

Reviewed on Aug 4, 2025

InterContinental Suites Hotel Cleveland by IHG

InterContinental Suites Hotel Cleveland by IHG

4 out of 5
Fairfax
Save 100% on your flight
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.8/10 Excellent! (1,003 reviews)
Hotel restaurant was excellent and room was cleanand quiet .The air purifier was a nice touch. The parking was too expensive and parking garage was never located.The beds were wey comfortable and roo. Air conditioning was very good. The staff was exceptional and early morning clerk at fro t desk helped with details about closed highway ramp detour i formation. The valets were great as well as the waiters and waitresses at the restaurant.

Reviewed on Aug 10, 2025

Hampton Inn & Suites Cleveland-Beachwood

Hampton Inn & Suites Cleveland-Beachwood

2.5 out of 5
Save 100% on your flight
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
9/10 Wonderful! (1,002 reviews)
Everyone is really nice

Reviewed on Aug 12, 2025

Holiday Inn Cleveland Clinic by IHG

Holiday Inn Cleveland Clinic by IHG

3 out of 5
Fairfax
Save 100% on your flight
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.8/10 Excellent! (1,153 reviews)
Excellent location and very good and clean facility.

Reviewed on Aug 11, 2025

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Discover the most popular places to visit in Highland Hills

Rock and Roll Hall of Fame showing interior views and music

Rock and Roll Hall of Fame

4.5/5(1,043 reviews)

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
Huntington Bank Field

Huntington Bank Field

4.5/5(294 reviews)

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
Beautiful ballpark, right in the heart of downtown Cleveland. Cleveland Indians - 7 Minnesota Twins - 6

Progressive Field

4.5/5(473 reviews)

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

Progressive Field

What to do in Highland Hills

Cleveland: Eerie Ghosts Haunted Walking Tour

Phantom's Parade on Prospect: Cleveland Ghost Tours

$24
per adult
100% of travellers recommend
Phantom's Parade on Prospect: Cleveland Ghost Tours
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
Hear Haunted Histories on Our cleveland Ghost Tour.

Cleveland Ghosts Tour

$32
per adult
90% of travellers recommend
Cleveland Ghosts Tour
See all activities in Highland Hills

Highland Hills Hotel Deals

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
$129 nightly
The price is $152 total per night from Aug 21 to Aug 22
$152 total
Aug 21 - Aug 22
Total includes taxes and fees
8.4/10 Very Good! (1,496 reviews)
"Elevators too slow; all weren’t used. Staff mostly friendly"

Reviewed on Aug 10, 2025

The Westin Cleveland Downtown
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
$130 nightly
The price is $153 total per night from Sep 2 to Sep 3
$153 total
Sep 2 - Sep 3
Total includes taxes and fees
8.8/10 Excellent! (1,010 reviews)
"The staff were so nice!"

Reviewed on Aug 11, 2025

Hyatt Regency Cleveland At The Arcade
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
$116 nightly
The price is $136 total per night from Aug 24 to Aug 25
$136 total
Aug 24 - Aug 25
Total includes taxes and fees
8.4/10 Very Good! (1,270 reviews)
"This hotel feels like it is slept on in downtown Cleveland and really is a great find! Right across the street from Rocket Arena, and a 5 minute walk to East 4th. The nearby dining options are great. Room was clean, comfortable bed, and lots of space to store items away in the room. The Keurig with ..."

Reviewed on Aug 12, 2025

Hotel Indigo Cleveland Downtown by IHG
See all 1,797 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.

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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 $498 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.