Title: Highland Hills Vacation Packages 2026 from $607 | Expedia.com [Hotels in Highland Hills](https://expedia.com/Highland-Hills-Hotels.d553248634983312698.Travel-Guide-Hotels)[Vacation Rentals in Highland Hills](https://expedia.com/Highland-Hills-Vacation-Rentals.d553248634983312698.Travel-Guide-VacationRentals)[Car Rentals in Highland Hills](https://expedia.com/Car-Rentals-In-Highland-Hills.d553248634983312698.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Highland Hills Vacations from $607 ## Book a Hotel + Flight or Car together to unlock savings ## 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](https://www.expedia.com/Case-Western-Reserve-University-University-Circle.d6066283.Vacation-Attraction), [Legacy Village](https://www.expedia.com/Legacy-Village-Cleveland.d553248621561735293.Vacation-Attraction) and [Pinecrest Plaza Shopping](https://www.expedia.com/Pinecrest-Plaza-Shopping-Cleveland.d650278886864773120.Vacation-Attraction) 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](https://images.trvl-media.com/lodging/1000000/870000/866100/866043/2d490d61_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Garden Inn Cleveland Downtown Downtown Cleveland Save 100% on your flight $607 per person Jun 4 - Jun 7 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Cleveland (CLE) 7.6/10 Good! (1,008 reviews) For the price of the room I was disappointed in the condition of it. The bathroom had holes in the shower and the ceiling was a mess. The elevator was dirty. Reviewed on Mar 28, 2026 ![The Inn at Fulton](https://images.trvl-media.com/lodging/103000000/102660000/102658400/102658389/2099735d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Inn at Fulton Save 100% on your flight $646 per person Jun 4 - Jun 7 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Cleveland (CLE) 8/10 Very Good! (35 reviews) Looked just like the pictures. Very clean. Only thing i would say is it only had one bathroom and that bathroom is located inside the master room so the other guest had to come in that room to use the bathroom so just be prepared for that. Other than that loved the area and place. Reviewed on Dec 27, 2025 ![The Washington Boutique Hotel](https://images.trvl-media.com/lodging/100000000/99990000/99982700/99982661/391bcf5c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Washington Boutique Hotel Save 100% on your flight $663 per person Jun 4 - Jun 7 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Cleveland (CLE) 9/10 Wonderful! (85 reviews) Room was clean and cute decor, there is no staff, more like an air bnb….and there is no parking. There a small parking lot on the s Reviewed on Mar 11, 2026 ![Kimpton Schofield Hotel by IHG](https://images.trvl-media.com/lodging/14000000/13190000/13181300/13181279/ba15d366_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kimpton Schofield Hotel by IHG Downtown Cleveland $689 per person Jun 4 - Jun 7 found 13 hours ago Roundtrip flight included Boston (BOS) to Cleveland (CLE) 8.8/10 Excellent! (1,026 reviews) Very nice hotel, staff were pleasant, and valet were quick Reviewed on Mar 29, 2026 ![The Westin Cleveland Downtown](https://images.trvl-media.com/lodging/1000000/10000/3400/3332/a3be6d16_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Cleveland Downtown Downtown Cleveland $1,205 per person Jun 4 - Jun 7 found 13 hours ago Roundtrip flight included Boston (BOS) to Cleveland (CLE) 8.6/10 Excellent! (2,084 reviews) My room could’ve been much more cleaner. There was a lot of dust everywhere and also they did not change out the lotion in the bathroom, which is pretty unsanitary. And this day and age is not OK to be reusing the same opened lotion bottles. Staff was very kind and very attentive. The only issue I had was trying to call the front desk. It took several times for me to do so. Breakfast was very mid not anything to brag about and honestly it cost too much four dollars for a cup of orange juice is ridiculous. I didn’t have issues with Parking as I used public transportation i.e. Lyft to get me to the hotel. Reviewed on Mar 29, 2026 Don't see what you're looking for? See all available trips from Columbus to Highland Hills [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CLE&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### Discover the most popular places to visit in Highland Hills ![Cleveland Clinic](https://images.trvl-media.com/place/859/5cdd9d1c-a594-49d8-b857-362b8aa568b1.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.com/Cleveland-Clinic-Fairfax.d6148324.Vacation-Attraction) ![Rock and Roll Hall of Fame](https://images.trvl-media.com/place/6066275/1693f855-4738-4134-869b-d02209a31816.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.com/Rock-And-Roll-Hall-Of-Fame-Downtown-Cleveland.d6066275.Vacation-Attraction) ![Progressive Field](https://images.trvl-media.com/place/859/faad48ec-f4c3-4455-ada7-7d8bb62b958e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.com/Progressive-Field-Downtown-Cleveland.d6034760.Vacation-Attraction) ### What to do in Highland Hills ![Skip the Line: Cleveland History Center Admission Ticket](https://mediaim.expedia.com/localexpert/1157628/25aef431-668a-41bb-873a-1c1f3e0e304b.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Skip the Line: Cleveland History Center Admission Ticket $14 per adult [](https://expedia.com/things-to-do/skip-the-line-cleveland-history-center-admission-ticket.a1157628.activity-details) ![Cleveland Cavaliers Basketball Game at Rocket Mortgage FieldHouse](https://mediaim.expedia.com/localexpert/47588377/af643437-058d-44db-9e0e-c012c9289dc7.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Cleveland Cavaliers Basketball Game at Rocket Mortgage FieldHouse $71 per adult [](https://expedia.com/things-to-do/cleveland-cavaliers-basketball-game-at-rocket-mortgage-fieldhouse.a47588377.activity-details) ![Cleveland: Eerie Ghosts Haunted Walking Tour](https://mediaim.expedia.com/localexpert/47691265/0d0cf914-0f1a-455e-bad3-f45e3f69856a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Phantom's Parade on Prospect: Cleveland Ghost Tours $32 per adult **100%** of travellers recommend [](https://expedia.com/things-to-do/phantoms-parade-on-prospect-cleveland-ghost-tours.a47691265.activity-details) [See all activities in Highland Hills](https://expedia.com/things-to-do/search?rid=553248634983312698) ## Highland Hills Hotel Deals ![Hotel Indigo Cleveland Downtown by IHG](https://images.trvl-media.com/lodging/1000000/120000/119000/119000/11326ddb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Indigo Cleveland Downtown by IHG 651 Huron Rd E Cleveland OH Fully refundable $105 nightly $124 total Apr 19 - Apr 20 Total with taxes and fees 8.4/10 Very Good! (1,608 reviews) Property was as is expected. Reviewed on Mar 29, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F19%2F2026&endDate=4%2F20%2F2026&selected=119000&PinnedHotelID=119000&HadPinnedHotel=true®ionId=553248634983312698) ![The Westin Cleveland Downtown](https://images.trvl-media.com/lodging/1000000/10000/3400/3332/a3be6d16_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Westin Cleveland Downtown 777 Saint Clair Ave Ne Cleveland OH Fully refundableReserve now, pay when you stay $109 nightly $128 total Apr 2 - Apr 3 Total with taxes and fees 8.6/10 Excellent! (2,104 reviews) My room could’ve been much more cleaner. There was a lot of dust everywhere and also they did not change out the lotion in the bathroom, which is pretty unsanitary. And this day and age is not OK to be reusing the same opened lotion bottles. Staff was very kind and very attentive. The only issue ... Reviewed on Mar 29, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F2%2F2026&endDate=4%2F3%2F2026&selected=3332&PinnedHotelID=3332&HadPinnedHotel=true®ionId=553248634983312698) ![Hotel Cleveland, Autograph Collection](https://images.trvl-media.com/lodging/1000000/20000/12400/12309/ffe01549_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Cleveland, Autograph Collection 24 Public Sq Cleveland OH Fully refundableReserve now, pay when you stay $118 nightly $139 total Apr 5 - Apr 6 Total with taxes and fees 9/10 Wonderful! (295 reviews) Bith breakfast and dinner were very good. Reviewed on Mar 27, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=12309&PinnedHotelID=12309&HadPinnedHotel=true®ionId=553248634983312698) [See all 1,869 properties in Highland Hills](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F31%2F2026&endDate=4%2F1%2F2026®ionId=553248634983312698) 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](https://www.expedia.com/The-Temple-Tifereth-Israel-Cleveland.d553248621561681669.Vacation-Attraction), [Pinecrest Plaza Shopping](https://www.expedia.com/Pinecrest-Plaza-Shopping-Cleveland.d650278886864773120.Vacation-Attraction) and [ETON Chagrin Blvd Shopping Center](https://www.expedia.com/ETON-Chagrin-Blvd-Shopping-Center-Cleveland.d553248623255232987.Vacation-Attraction) | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.com/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.com/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.com/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ Friendly Vacations [](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adventure Vacations [](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Highland Hills vacation package cost? ### What are the cheapest months to go to Highland Hills? ### How many days is enough for Highland Hills? ### How to find the best Highland Hills package deals? ### Is it cheaper to book a Highland Hills vacation as a package? ### When to book a vacation package to Highland Hills? ### 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](https://www.expedia.com/why/trip-planning): 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](https://www.expedia.com/Things-To-Do-In-Highland-Hills.d553248634983312698.Travel-Guide-Activities) with our dedicated activity guide. ### Does Expedia offer Book Now, Pay Later Highland Hills vacation packages? \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.