Highland Hills Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Highland Hills
The Westin Cleveland Downtown
777 Saint Clair Ave Ne Cleveland OH
Fully refundableReserve now, pay when you stay
S$222
3 Sept - 4 Sept
includes taxes & fees
8.6/10 Excellent! (248 reviews)
"We just got back from a trip to Cleveland to attend a concert and visit Rock Hall. The Good: The hotel is located only a short walk to not only Rock Hall but other downtown attractions. The front desk staff were very welcoming. The gym is one of the best hotel gyms I’ve visited. Very nice equipment! ..."
Reviewed on 24 Aug, 2026
Hotel Indigo Cleveland Downtown by IHG
651 Huron Rd E Cleveland OH
Fully refundable
S$158
7 Sept - 8 Sept
includes taxes & fees
8.4/10 Very good! (1,861 reviews)
"The Indigo is the perfect place to stay for sporting events,. I love baseball, and you can walk to the stadium in 5 minutes. The basketball arena is oeven nearer. There's plenty of great food and drink establishments very close by. The Indigo is comfy and clean, with a friendly staff. I highly recommend ..."
Reviewed on 24 Aug, 2026
Crowne Plaza Cleveland at Playhouse Square by IHG
1260 Euclid Ave Cleveland OH
Fully refundable
S$170
30 Aug - 31 Aug
includes taxes & fees
9/10 Wonderful! (1,422 reviews)
"Perfect location and friendly staff. Rooms were very clean, comfortable and well maintained."
Reviewed on 24 Aug, 2026
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.
What to do in Highland Hills
Cleveland Guardians Baseball Game at Progressive Field
S$99
per adult
Phantom's Parade on Prospect: Cleveland Ghost Tours
S$31
per adult
100% of travellers recommend
Cleveland Browns Football Game at Cleveland Browns Stadium
S$2,429
per adult
Frequently asked questions
How much does a Highland Hills holiday package cost?
You can grab a holiday package to this destination on Expedia. However, how much your holiday 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're likely to find lower rates and greater availability in January, February and November. Explore our cheap Highland Hills holiday packages and you could land some great off-season discounts.
How many days is enough for Highland Hills?
The ideal duration of your Highland Hills holiday depends on what you'd like to see. Typically, a handful of days to a week will give you enough time to visit all the leading attractions and discover some hidden spots along the way.
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 holiday package as soon as possible.
Is it cheaper to book a Highland Hills holiday as a package?
Expedia holiday 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 customised Highland Hills holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday 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?
- Pick the perfect time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Highland Hills.
- Calculate your budget: Ensure you have enough money to pay for everything from transportation and food to activities and airfares. Your hotel will likely be the largest expense during your trip to Highland Hills.
- Work out your trip length: Consider how much time you want to spend exploring Highland Hills. Plan your itinerary so you can get to all the activities and attractions you're interested in at a comfortable pace.
- Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a personalised Highland Hills holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
