Deals on vacations and trips to Highland

Save when you book Highland package deals

Choose two or more items and save on your trip:

Highland flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
White House at Grand Central

White House at Grand Central

3.5 out of 5
Grand Center
Price was $742, price is now $577 per person
$577
per person
Jul 8 - Jul 15
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to St. Louis (STL)
This apartment features a garden, express check-out, and laundry facilities. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. The front desk is staffed around-the-clock and barbecue grills are on offer.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $2,025, price is now $971 per person
$971
per person
Jul 8 - Jul 15
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to St. Louis (STL)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like continental breakfast and free self parking.
The Cheshire

The Cheshire

4 out of 5
Save 100% on your flight
Price was $1,072, price is now $784 per person
$784
per person
Jul 8 - Jul 15
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to St. Louis (STL)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and free English breakfast each morning.
Crowne Plaza St. Louis Airport by IHG

Crowne Plaza St. Louis Airport by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,010, price is now $749 per person
$749
per person
Jul 8 - Jul 15
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to St. Louis (STL)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the gym and perks like a free area shuttle.
The West End

The West End

2 out of 5
Central West End
Price was $753, price is now $636 per person
$636
per person
Jul 8 - Jul 15
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to St. Louis (STL)
A 24-hour gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Express check-out, luggage storage, and barbecue grills are also on offer.

Top Highland hotels deals

Seasons Inn & Suites Highland

Seasons Inn & Suites Highland

2.5 out of 5
20 Central Blvd Highland IL
Free Cancellation
Reserve now, pay when you stay
$122 nightly
The price is $135 total per night
$135 total
May 20 - May 21
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Craftsman styled home in the heart of downtown Highland

Craftsman styled home in the heart of downtown Highland

Highland IL
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
The Loft on the Square

The Loft on the Square

Highland IL
Get rates
A gym is featured at this apartment, along with laundry facilities.
Kitchen
Washer
The Swiss Post Apartment A

The Swiss Post Apartment A

Highland IL
Get rates
This apartment features laundry facilities.
The Swiss Post Apartment B

The Swiss Post Apartment B

Highland IL
Get rates
This apartment features laundry facilities.
Drury Inn & Suites St. Louis Fairview Heights

Drury Inn & Suites St. Louis Fairview Heights

3 out of 5
12 Ludwig Dr Fairview Heights IL
Free Cancellation
Reserve now, pay when you stay
$96 nightly
The price is $108 total per night
$108 total
May 24 - May 25
Total with taxes and fees
This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Highland
View all properties
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.

Popular places to visit

Sunny morning on a Silver lake in Wisconsin

Silver Lake Park

Explore the great outdoors at Silver Lake Park, a lovely green space in Highland. Stroll along the lakeside or experience the area's festivals.

Silver Lake Park

Korte Recreation Center

Catch an event at Korte Recreation Center during your trip to Highland. Stroll along the lakeside or experience the area's festivals.

Korte Recreation Center

Frequently asked questions

How much are vacation packages to Highland?
Packages, which include hotels and flights in Highland, are priced from as little as $577. Make your travel dreams a reality and begin your booking with Travelocity today.
How long should my Highland vacation be?
Many people secure their hotel for 2 nights in Highland. But that doesn't necessarily mean you have to. How long you choose to stay comes down to what you hope to do on your vacation. If you intend to familiarize yourself with every nook and cranny of this fantastic destination, consider booking another night or so (or even longer!).
Where can I get the best vacation package deals for Highland?
Check out Travelocity. With access to 400 airlines and a whopping 1,000,000 properties across the globe, finding the perfect Highland package deal couldn't be easier.
Why should I book my Highland vacation package with Travelocity?
By booking your flights, hotel, activities and car rental all in the one place, you'll save both time and money. All our bookings come with a professional customer service support team available round-the-clock, and you'll know that you'll always be getting the best deal possible with our Price Match Guarantee. So, what are you waiting for? Book the getaway of your dreams today and get packing!
Can I save money on my Highland car rental if I bundle it with my hotel or flight?
With a Highland vacation package, you can bundle your flight, car and hotel bookings and save a ton. If you're in the mood to explore the best of this impressive location, why not make a beeline for Missouri Botanical Gardens and Arboretum? This famous attraction is 35 mi from Highland. With your own set of wheels, you'll be there in a jiffy.
Which airport is best for Highland?
Lambert-St. Louis Intl. Airport (STL) is located approximately 40 mi west of central Highland.
What is there to do in Highland?
While hopping off the tourist trail is no doubt rewarding, you shouldn't miss the well-known sights that make a destination famous. Silver Lake Park and Korte Recreation Center are a couple of them in Highland.
Where should I stay when visiting Highland?
If you're searching for somewhere to lay your head, consider the Seasons Inn & Suites Highland. It's the top choice for many travelers.

Photos of local treasures

Browse Highland vacation photos for more inspiration

City Hall in Highland, Illinois

Explore More Ways to Travel with Travelocity