Highland Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to ￥45,448 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Find the Best Highland Vacation Packages

Highland Hotel Deals

Highland: Driftless Fun Awaits
Highland: Driftless Fun Awaits
Highland
The price is ￥15,169 per night from Jul 21 to Jul 22
￥15,169
￥30,918 total
Jul 21 - Jul 22
includes taxes & fees
10/10 Exceptional! (1 review)
"Great property. Had everything we needed. Highly recommend."

Reviewed on May 27, 2025

Highland: Driftless Fun Awaits
Cheese Wedge Cabin Idyllic Farm
Cheese Wedge Cabin Idyllic Farm
Highland
The price is ￥39,729 per night from Jul 8 to Jul 9
￥39,729
￥48,298 total
Jul 8 - Jul 9
includes taxes & fees
Cheese Wedge Cabin Idyllic Farm
Don Q Inn
Don Q Inn
2.5 out of 5
3658 State Road 23, Dodgeville, WI
Fully refundableReserve now, pay when you stay
8/10 Very Good! (1,002 reviews)
"Very friendly. Rooms are outdated. Was locked out of my room at 3:00 am because my key wouldn’t work."

Reviewed on Jul 3, 2025

Get rates
Don Q Inn
See all 120 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.

Frequently asked questions

How much does a Highland vacation package cost?
You can grab a vacation package to this top destination on Expedia. However, how much your vacation to Highland costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Highland?
You're likely to find reduced prices and greater availability in January, February and April. Explore our cheap Highland vacation packages and you could score some great off-season discounts.
How many days is enough for Highland?
Usually, a handful of days is enough to explore the main attractions during your Highland vacation. However, if you'd like to have more time to relax or take day tours, think about extending your trip.
How to find the best Highland package deals?
Start your search for a Highland package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select some filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Highland package deal right away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Highland adventure off to a flying start.
Is it cheaper to book a Highland vacation as a package?
You can enjoy significant savings on your Highland retreat by booking a tailored vacation package. Check the "Package" heading, then select your travel dates and destination to view some great airfares and hotel prices. Bundle everything into a neat 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?
If you're considering a spur-of-the-moment Highland adventure, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Highland?

  1. Pick your travel dates: The things you'd like to do in Highland and your preferred season will help you decide when to get away.
  2. Work out your budget: Make sure you have enough money to pay for everything from food and transportation to flights and activities. Your hotel will probably be the largest expense during your trip to Highland.
  3. Decide how long to go for: Now that you're up to speed on Highland, you can figure out the perfect length of your break. Create a draft plan and allocate enough time to cover everything you want to see.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to choose 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.