Highland Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Highland Holiday

Our pick of the best Highland Hotel Deals

Cheese Wedge Cabin Idyllic Farm

Cheese Wedge Cabin Idyllic Farm

Highland WI
8.8/10 Excellent! (3 reviews)
"Wonderful experience! Host is amazing! Really hoping to come back soon! Words cannot describe how lovely our time there was!"

Reviewed on 18 Sept 2026

Get rates
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
The price is NZ$152 per night from 1 Dec to 2 Dec
NZ$152
1 Dec - 2 Dec
includes taxes & fees
8/10 Very good! (1,004 reviews)
"The property was delightful. It needs some upkeep but even with that we enjoyed and would visit again."

Reviewed on 8 Nov 2026

Don Q Inn
Sleep Inn & Suites Lancaster-Platteville

Sleep Inn & Suites Lancaster-Platteville

2.5 out of 5
1600 S Madison Street Lancaster WI
Fully refundable
The price is NZ$181 per night from 6 Dec to 7 Dec
NZ$181
6 Dec - 7 Dec
includes taxes & fees
9.4/10 Exceptional! (395 reviews)
"Easy parking, decent breakfast, clean room and comfortable"

Reviewed on 8 Nov 2026

Sleep Inn & Suites Lancaster-Platteville
See all 125 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.

Stay near popular Highland attractions

Blackhawk Lake Recreation Area

10.0/10 (2 reviews)
Explore the great outdoors at Blackhawk Lake Recreation Area, a lovely green space in Highland. Stroll along the lakeside or discover the area's waterfalls.
See properties

Frequently asked questions

How much does a Highland holiday package cost?
You can grab a holiday package to this top destination on Expedia. However, how much your holiday 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 holiday 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 holiday. 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 holiday as a package?
You can enjoy significant savings on your Highland retreat by booking a tailored holiday 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 holiday 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 holiday 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.