Highland Vacation Packages

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Top Highland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Rodeway Inn Kansas City Downtown Area

Rodeway Inn Kansas City Downtown Area

2 out of 5
Northeast Kansas City
per person
Sep 12 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Kansas City (MCI)
5/10 (165 reviews)
Liked the rooms and amenities.

Reviewed on Jan. 7, 2025

Southmoreland on the Plaza an Urban Inn

Southmoreland on the Plaza an Urban Inn

3.5 out of 5
Midtown - Westport
per person
Sep 12 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Kansas City (MCI)
9.4/10 Exceptional! (383 reviews)
Loved this property. No host on site, but they did a great job of communicating. Will definitely stay here again.

Reviewed on Aug. 12, 2025

The Inn at Meadowbrook

The Inn at Meadowbrook

4 out of 5
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Kansas City (MCI)
9.8/10 Exceptional! (360 reviews)
This hotel is our families favorite! Anytime we are in town this is where we stay! The cleanest, most comfortable and friendly hotel around!

Reviewed on Aug. 12, 2025

Stoney Creek Hotel Kansas City - Independence

Stoney Creek Hotel Kansas City - Independence

3.5 out of 5
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Kansas City (MCI)
9.2/10 Wonderful! (2,257 reviews)
It was pet friendly hotel, but did not have the odors associated with pets. The hotel and surroundings were very clean and fresh. The staff was very pleasant and cordial, we will recommend to friends/family.

Reviewed on Aug. 13, 2025

Holiday Inn Hotel & Suites Overland Park - Convention Center by IHG

Holiday Inn Hotel & Suites Overland Park - Convention Center by IHG

3 out of 5
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Kansas City (MCI)
8.8/10 Excellent! (889 reviews)
Was really nice and comfortable. Will be staying at holiday inn again

Reviewed on Aug. 13, 2025

Ready to book your vacation to Highland?

 

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Highland Hotel Deals

Homey Cottage With Sunroom & Smart TV!

Homey Cottage With Sunroom & Smart TV!

3 out of 5
Highland
10/10 Exceptional! (5 reviews)
Cute, comfortable, and clean
"Cute, comfortable, and clean. The kitchen has everything you need to prepare meals. Also has an assortment of games and books."

Reviewed on Jul. 13, 2025

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Homey Cottage With Sunroom & Smart TV!
Peaceful Kansas Cottage w/ Wraparound Deck!

Peaceful Kansas Cottage w/ Wraparound Deck!

3 out of 5
Highland
AMAZING!!! Wondeful place and an amazing value.
"This was an amazing place. Very well kept and beautiful. Absolutely wonderful to stay there and the communications was 5/5 stars. Such a welcoming owner. Great porch. Very quiet. LOVELY!!!"

Reviewed on Oct. 24, 2024

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Peaceful Kansas Cottage w/ Wraparound Deck!
Holiday Inn Express Hotel & Suites St. Joseph by IHG

Holiday Inn Express Hotel & Suites St. Joseph by IHG

2.5 out of 5
3600 N. Village Dr., St. Joseph, MO
Fully refundable
The price is CA $151 per night from Aug 17 to Aug 18
CA $151
CA $175 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (756 reviews)
Great breakfast
"The breakfast selection was fantastic."

Reviewed on Aug. 9, 2025

Holiday Inn Express Hotel & Suites St. Joseph by IHG
See all 91 properties in Highland
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

How much does a Highland vacation package cost?
You'll find cheap prices from CA $915 on Expedia for your Highland escape. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Highland costs.
What are the cheapest months to go to Highland?
Travel in the off-peak season and you're likely to score cheap Highland vacation packages. Bear in mind that school vacation periods and major local events can have an impact on prices, so do your research before you go.
How many days is enough for Highland?
Usually, a handful of days is enough to check out the major sights during your Highland vacation. But if you prefer to have some time to unwind or take day trips, consider extending your itinerary.
How to find the best Highland package deals?
Landing a cheap Highland package deal is a breeze with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget range, apply a few filters and browse what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Highland package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Highland vacation as a package?
You can enjoy significant savings on your Highland escape by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to see the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Highland?
Secure incredible bargains by booking your flights in advance with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Highland trip.
How to plan a trip to Highland?

  1. Choose your dates: What you want to do in Highland and your preferred season can help you decide when to travel.
  2. Set a budget: Consider expenses like transportation, flights and meals when working out how much to set aside for your trip to Highland. Then, choose a hotel that matches your budget, whether that's a wallet-friendly stay or a swankier retreat.
  3. Work out your trip length: Consider how much time you want to spend exploring Highland. Plan your days so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to find a Highland vacation package that brings all your bookings together.

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