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Highland Vacations from $348

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Your Highland Vacation

When a getaway to the city is calling your name, answer it with a vacation package to Highland. With all your travel arrangements under control before you go, all you need to do here is focus on making unforgettable memories. Korte Recreation Center and Silver Lake Park are among the top attractions to tour during your trip to Highland. Whoever you're going away with and whatever the size of your budget, your dream Highland vacation is only clicks away with Expedia.

The Latest Highland Vacation Packages

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Where to stay near Highland

Highland offers a delightful blend of outdoor adventures and romantic scenery. Explore the charming Heart of Highland, stroll through Salem Place, or venture into the inviting Chicago suburbs for family-friendly excursions. Experience the area's art scene and enjoy wellness and relaxation amidst its beautiful landscapes.

A city skyline with a prominent arch landmark, several high-rise buildings, and boats on a river.

A city skyline with a prominent arch bridge reflecting on the water.

A large arch structure with a lit interior, set against a sunset sky.

A multi-level pedestrian bridge with railings, a clear blue sky, and a city skyline in the background.

A stone bridge, a small waterfall, a gazebo, and a white picket fence in a park.

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O'Fallon

Discover O'Fallon, a welcoming destination perfectly suited for family travelers seeking a blend of outdoor adventures and vibrant city experiences. With attractions like the Gateway Arch and the lively Gateway Conference Center, O'Fallon offers a rich array of activities and venues. Visitors can also enjoy the local parks and McKendree University, making it an ideal spot for weekend getaways. Located about 16 miles from Highland, O'Fallon is a smart choice for your next hotel booking.

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A historic downtown sign with a building illustration and founding year.

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Troy

Experience the charm of Troy, a top-rated choice for family travelers and weekend getaway seekers who want to enjoy a blend of outdoor activities and entertainment. With attractions like the Gateway Conference Center and the serene Gardens at SIUE, there's something for everyone. Troy’s vibrant atmosphere is complemented by its proximity to a sports facility stadium and the Edwardsville Arts Center, making it a perfect hub for exploration. Located about 13 miles from Highland, Troy offers a smart choice for your stay.

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Pierron

If you are a family or outdoor enthusiast, look no further than Pierron, which features beautiful recreational areas like Silver Lake Park and Patriot's Park, perfect for a day of fun and relaxation. Known for its scenic surroundings, Pierron also offers a charming atmosphere for those seeking romance. Located about 5 miles from Highland, it provides easy access to local attractions, making Pierron a smart choice for your stay in the area.

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St. Jacob

St. Jacob stands out as a prime spot for travelers seeking family-friendly experiences, outdoor adventures, and romantic getaways. Here, visitors can explore the scenic Silver Lake Park, enjoy the vibrant atmosphere at McKendree University, and attend events at the Gateway Conference Center. With its welcoming charm, St. Jacob is only about 5 miles from Highland, making it an ideal base for your vacation. Choose St. Jacob for a memorable stay that combines relaxation and exploration.

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Grantfork

Travelers visiting the area often choose Grantfork, especially those seeking a blend of outdoor scenery and family-friendly experiences. With its charming recreational areas, including Silver Lake Park and Patriot's Park, visitors can enjoy leisurely walks and vibrant nature. The nearby McKendree University adds a touch of local culture to your stay. Located about 6 miles from Highland, Grantfork offers a refreshing getaway that caters to both relaxation and adventure, making it an excellent choice for your vacation.

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Discover the most popular places to visit in Highland

Silver Lake Park

Rating: 8.8/10 (5 reviews)

Silver Lake Park surrounds a 550-acre lake with scenic hiking trails and abundant wildlife. Enjoy boating, fishing, or playing a round at the 18-hole disc golf course while taking in the tranquil woodland setting.

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Korte Recreation Center

Rating: 6.0/10 (1 review)

This community hub features an indoor pool with a lazy river and water slide, plus a fitness center and gymnasium. Enjoy family-friendly recreation year-round, perfect for escaping Illinois weather while staying active.

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Highland Hotel Deals

Seasons Inn & Suites Highland

A hotel room with a large bed, a red bedspread, a bathtub, a nightstand with a lamp, and two framed pictures on the wall.
  • Address: 20 Central Blvd, Highland, IL, 62249, US
  • Location: 0.9 mi from Highland
  • Star rating: 2.5/5
  • Guest rating: 8/10 (Very good, 702 reviews)
  • Price: $94 nightly, $104 total, Nov 29 - Nov 30, Total with taxes and fees

Holiday Inn Express Troy by IHG

A reception area with two reception desks, a wall-mounted sign, and a patterned carpet.
  • Address: 2011 Formosa Road, Troy, IL, 62294, US
  • Location: 13.1 mi from Highland
  • Star rating: 2.5/5
  • Guest rating: 9.4/10 (Exceptional, 847 reviews)
  • Price: $111 nightly, $123 total, Dec 13 - Dec 14, Total with taxes and fees

Powhatan Motel

A neatly made bed with a patterned bedspread, a framed picture above it, a chair, a lamp, and a checkered floor.
  • Address: 8 O'fallon St., Pocahontas, IL, 62275, US
  • Location: 9.1 mi from Highland
  • Star rating: 2.5/5
  • Guest rating: 8.6/10 (Excellent, 231 reviews)
  • Price: $97 nightly, $103 total, Nov 15 - Nov 16, Total with taxes and fees
  • Review: Food excellent

Best Western Plus MidAmerica Hotel

A spacious lobby with a modern design, featuring a large seating area with leather chairs, a kitchen area with a counter and appliances, and a flat-screen TV mounted on the wall.
  • Address: 9730 Hayden Drive, Mascoutah, IL, 62258, US
  • Location: 14.9 mi from Highland
  • Star rating: 2.5/5
  • Guest rating: 9/10 (Wonderful, 1001 reviews)
  • Price: $101 nightly, $115 total, Nov 16 - Nov 17, Total with taxes and fees
  • Review: The shuttle was a few minutes late and the driver looked like he just got out of bed. Not very professional at all.

Super 8 by Wyndham Troy IL/St. Louis Area

An indoor swimming pool with a lifeguard chair, a lifebuoy, and a mural of a beach scene.
  • Address: 910 Edwardsville Rd, Troy, IL, 62294, US
  • Location: 13.2 mi from Highland
  • Star rating: 2/5
  • Guest rating: 8.2/10 (Very good, 1003 reviews)
  • Price: $64 nightly, $71 total, Dec 7 - Dec 8, Total with taxes and fees
  • Review: Incredible value. I was hesitant because of the low cost but I had a nice stay and have no complaints.

Red Roof Inn St Louis - Troy, IL

A lobby with a chandelier, seating area, and a reception desk.
  • Address: 2030 Formosa Road, Troy, IL, 62294, US
  • Location: 13.1 mi from Highland
  • Star rating: 2/5
  • Guest rating: 7.8/10 (Good, 1004 reviews)
  • Price: $65 nightly, $72 total, Nov 22 - Nov 23, Total with taxes and fees

Days Inn by Wyndham Troy IL

A modern kitchen with marble countertops, a built-in coffee station, and a seating area with metal chairs and tables.
  • Address: 910 Cherry Ln, Troy, IL, 62294, US
  • Location: 13.2 mi from Highland
  • Star rating: 2/5
  • Guest rating: 7.8/10 (Good, 348 reviews)
  • Price: $74 nightly, $82 total, Nov 16 - Nov 17, Total with taxes and fees
  • Review: Place was nice did have some bugs and a little sketch outside at night but besides that place was okay would stay again if needed

Spark by Hilton Troy

A hotel room with two beds, a desk, a chair, a wardrobe, and a window with curtains.
  • Address: 2020 Formosa Drive, Troy, IL, 62294, US
  • Location: 13.1 mi from Highland
  • Star rating: 3/5
  • Guest rating: 8.4/10 (Very good, 5 reviews)
  • Price: $93 nightly, $103 total, Dec 3 - Dec 4, Total with taxes and fees

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

What's the best vacation package for Highland?

For travelers seeking romantic getaways in Highland, a package built around a stay at Seasons Inn & Suites Highland offers a comfortable base. This hotel, located about 1 mile from central Highland, features an indoor pool and free WiFi, with travelers often praising the nice staff and comfortable rooms, noting the beautiful location. It's also a convenient starting point for exploring scenic outdoor areas like Silver Lake Park, about 1 mile away.


Families planning a Highland vacation package will find Seasons Inn & Suites Highland a practical choice. Its indoor pool provides a great option for kids, and the complimentary breakfast helps start the day easily. The hotel is also well-situated for family-friendly attractions such as Korte Recreation Center, about 2 miles from central Highland.


If you're looking for the best value vacation packages in Highland, Seasons Inn & Suites Highland is a strong option, as nearly all hotels in the area fall into a midrange price tier. Its free breakfast and free WiFi add to the overall value, making it a budget-friendly choice for your trip.

How can I save money on a Highland vacation package?

When you bundle, you can save up to 30%*. To save money on a Highland package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

What are the top things to do in Highland?

Highland is an outdoor and nature destination, offering a variety of activities for your Highland vacation:


Browse and book things to do in Highland on Expedia.

Do you need to rent a car in Highland, or is public transport enough?

For a Highland vacation package, a rental car is highly recommended to explore the area. Highland is an outdoor and nature destination, and its attractions are spread across the area, making a rental car the most flexible option for your Highland vacation packages with flights. For instance, popular spots like Copper Dock Winery are about 14 miles from central Highland, and Cave of The Mounds National Natural Landmark is about 16 miles away. St. Louis Lambert International Airport (STL) is about 37 miles from central Highland, and a car allows you to easily reach these natural sites and other points of interest at your own pace.

Can I change or cancel my Highland vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking Highland vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later Highland vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Highland vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to Highland?

To find last-minute vacation packages to Highland, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on Highland vacation packages?

Free cancellation on a Highland vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a Highland vacation as a package or separately?

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Highland getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my Highland vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.