Highland Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Highland
Don Q Inn
3658 State Road 23 Dodgeville WI
Fully refundableReserve now, pay when you stay
S$110
13 Sept - 14 Sept
includes taxes & fees
Sleep Inn & Suites Lancaster-Platteville
1600 S Madison Street Lancaster WI
Fully refundable
S$126
20 Sept - 21 Sept
includes taxes & fees
9.4/10 Exceptional! (360 reviews)
"The hot tub tucked! Warm water like a bath tub water you have been in for awhile. Couldn't even sit in it!"
Reviewed on 26 Aug, 2026
Dodgeville inn and suites
1308 n johns st Dodgeville WI
Fully refundableReserve now, pay when you stay
S$103
30 Aug - 31 Aug
includes taxes & fees
7.2/10 Good! (91 reviews)
"An old place. Musty and moldy smell. My wife couldn’t breathe - she has asthma. Had to check out early and was told we might not get a refund. We’ll see what happens, but this place was just rundown."
Reviewed on 23 Aug, 2026
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
Beach at Black Hawk Lake Recreation Area
Why not spend a lazy afternoon at Beach at Black Hawk Lake Recreation Area during your trip to Highland? While you're in the area, wander around the parks.
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.
Spurgeon Vineyards & Winery
9.0/10 (2 reviews)
You can enjoy a tasting or tour at Spurgeon Vineyards & Winery during your travels to Highland. While you're in the area, wander around the natural setting.
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?
- 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.
- 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.
- 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.
- 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
