Highland Hills Vacations from $475

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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.
Hilton Garden Inn Cleveland Downtown

Hilton Garden Inn Cleveland Downtown

3 out of 5
Downtown Cleveland
Save 100% on your flight
Price was $712, price is now $475 per person
$475
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
7.6/10 Good! (1,006 reviews)
Close to Guardians stadium made it very nice. Close to downtown. Nice to be able to park there and walk to the game.

Reviewed on Jun 1, 2026

Fidelity Hotel

Fidelity Hotel

4.5 out of 5
Downtown Cleveland
Save 100% on your flight
Price was $1,094, price is now $722 per person
$722
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
9.6/10 Exceptional! (756 reviews)
Truly the “luxury hotel” experience we were hoping for. Fabulous stay, will be back for sure!

Reviewed on May 31, 2026

Ariel Broadway Hotel

Ariel Broadway Hotel

3.5 out of 5
Save 100% on your flight
Price was $714, price is now $490 per person
$490
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.2/10 Very Good! (582 reviews)
Cool historic hotel in downtown Lorain. I would stay there again.

Reviewed on Jun 3, 2026

InterContinental Cleveland by IHG

InterContinental Cleveland by IHG

4.5 out of 5
Fairfax
Save 100% on your flight
Price was $1,100, price is now $761 per person
$761
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
9/10 Wonderful! (893 reviews)
Everyone was so nice!

Reviewed on May 29, 2026

Landing Apartments near Rivergate Park Area

Landing Apartments near Rivergate Park Area

4 out of 5
Cuyahoga Valley
Save 100% on your flight
Price was $1,119, price is now $774 per person
$774
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
9.6/10 Exceptional! (4 reviews)
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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
$117 nightly
The price is $137 total per night from Jun 21 to Jun 22
$137 total
Jun 21 - Jun 22
Total with taxes and fees
8.4/10 Very Good! (1,699 reviews)
"The room was clean and the bed was very comfortable. Elevator was slow, but there was an uprade in the process of beng completed. Close to Progressive Field and Rocket Arena. Rock and Roll Hall of Fame was about a 20 mins. walk. Most things were in reaosnable walking distance-restaurants, Downtown ..."

Reviewed on Jun 3, 2026

Hotel Indigo Cleveland Downtown by IHG
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
$149 nightly
The price is $175 total per night from Jun 21 to Jun 22
$175 total
Jun 21 - Jun 22
Total with taxes and fees
8.8/10 Excellent! (2,194 reviews)
"Maintenance 24-7, even over a holiday weekend was obnoxious! Give your guests a break, at least at night."

Reviewed on Jun 2, 2026

The Westin Cleveland Downtown
Hilton Garden Inn Cleveland Downtown

Hilton Garden Inn Cleveland Downtown

3 out of 5
1100 Carnegie Ave Cleveland OH
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $124 total per night from Jun 21 to Jun 22
$124 total
Jun 21 - Jun 22
Total with taxes and fees
7.6/10 Good! (1,012 reviews)
"It was a clean hotel with a very friendly staff. We made use to the restaurant everyday. The food prices were very reasonable and we enjoyed the food and talking to the staff. We would definitely stay there again."

Reviewed on Jun 2, 2026

Hilton Garden Inn Cleveland Downtown
See all 1,879 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 $475 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.