Highland Hills Vacations from $188

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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.
Towneplace Suites By Marriott Cleveland Westlake

Towneplace Suites By Marriott Cleveland Westlake

3 out of 5
Save 100% on your flight
Price was $256, price is now $188 per person
$188
per person
Jan 16 - Jan 19
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Cleveland (CLE)
15.6/10 Exceptional! (454 reviews)
convenient and good value

Reviewed on Oct 16, 2025

Fidelity Hotel

Fidelity Hotel

4 out of 5
Downtown Cleveland
Save 100% on your flight
Price was $495, price is now $327 per person
$327
per person
Feb 6 - Feb 9
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Cleveland (CLE)
19.2/10 Exceptional! (471 reviews)
Loved everything about this place. Staff, vibe and location were all wonderful. Would definitely stay again!

Reviewed on Nov 18, 2025

Hampton Inn & Suites Cleveland/Independence

Hampton Inn & Suites Cleveland/Independence

2.5 out of 5
Price was $366, price is now $258 per person
$258
per person
Feb 6 - Feb 9
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Cleveland (CLE)
17.6/10 Exceptional! (1,001 reviews)
It was clean and staff were nice. One suggestion in handicap accessible rooms toilets should be handicap as well. They were too low with nothing to hold on to when lowering yourself.

Reviewed on Nov 15, 2025

Hilton Garden Inn Cleveland Downtown

Hilton Garden Inn Cleveland Downtown

3 out of 5
Downtown Cleveland
Price was $384, price is now $275 per person
$275
per person
Feb 6 - Feb 9
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Cleveland (CLE)
14.8/10 Exceptional! (1,004 reviews)
Natalie was great ! Shes the best

Reviewed on Nov 18, 2025

Hotel Indigo Cleveland Downtown by IHG

Hotel Indigo Cleveland Downtown by IHG

3.5 out of 5
Downtown Cleveland
Price was $379, price is now $272 per person
$272
per person
Feb 6 - Feb 9
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Cleveland (CLE)
16.8/10 Exceptional! (1,442 reviews)
Everything was awesome and clean. Short walk to Rocket Arena. Nice atmosphere and good bar foods. The only thing that was a issue was, they lost my keys at Valet parking.

Reviewed on Nov 17, 2025

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Discover the most popular places to visit in Highland Hills

Huntington Bank Field

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

Progressive Field

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

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

$23
per adult
Cleveland Cavaliers Basketball Game at Rocket Mortgage FieldHouse
Cleveland: Eerie Ghosts Haunted Walking Tour

Phantom's Parade on Prospect: Cleveland Ghost Tours

$26
per adult
100% of travellers recommend
Phantom's Parade on Prospect: Cleveland Ghost Tours
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
$109 nightly
The price is $128 total per night from Nov 20 to Nov 21
$128 total
Nov 20 - Nov 21
Total with taxes and fees
8.6/10 Excellent! (1,776 reviews)
Great view!! AWESOME STAY

Reviewed on Nov 16, 2025

The Westin Cleveland Downtown
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
$106 nightly
The price is $125 total per night from Dec 18 to Dec 19
$125 total
Dec 18 - Dec 19
Total with taxes and fees
8.4/10 Very Good! (1,442 reviews)
Very nice room. Spacious. Easy check in. Good customer service

Reviewed on Nov 11, 2025

Hotel Indigo Cleveland Downtown by IHG
Best Western Plus Strongsville Cleveland

Best Western Plus Strongsville Cleveland

3 out of 5
15471 Royalton Rd Strongsville OH
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $79 total per night from Nov 23 to Nov 24
$79 total
Nov 23 - Nov 24
Total with taxes and fees
7.4/10 Good! (1,203 reviews)
Everything was clean. Staff was good and polite. Breakfast was the typical hotel breakfast but good and fresh.

Reviewed on Nov 16, 2025

Best Western Plus Strongsville Cleveland
See all 1,849 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 $188 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.