Highland Vacations from $465
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Your Highland Vacation
Memorable adventures await when you reserve a vacation package to Highland. Whether you're a foodie, history enthusiast or just a traveler who loves to experience new places, there's something for everyone in this interesting city. If sightseeing is on the cards during your trip to Highland, visit popular attractions like Blackhawk Lake Recreation Area, Beach at Black Hawk Lake Recreation Area and Spurgeon Vineyards & Winery. Whoever you're going away with and whatever the size of your budget, your ultimate Highland vacation is just a few clicks away with Expedia.
The Latest Highland vacation packages
Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham Dubuque
$465
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Dubuque (DBQ)
6.4/10 (1,000 reviews)
The bar was there but never open. You can only enter at the main entrance as the key reader on the east end of the property didnt work. My room smelled like an old basement and most of everything was old or really worn. Plus the guy who painted the walls got more paint on everything but the walls. I had a kit cat from the vending machine and it was so old it had melted in the package. The TV had to be turned on manually and the remote only change channels not even volume. There was biscuits and gravy for breakfast and waffle makers plus a toaster and bread, cereal, terrible coffee. Also no phone to contact anyone.
Reviewed on Sep 28, 2026
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.
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.
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.
Highland Hotel Deals
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 Sep 18, 2026
Don Q Inn
3658 State Road 23 Dodgeville WI
Fully refundableReserve now, pay when you stay
$80 nightly
$91 total
Nov 4 - Nov 5
Total with taxes and fees
8/10 Very Good! (1,004 reviews)
"My room was clean and comfortable, though it could use a little updating in terms of the colors and the carpet. It was fine for my one-night stay. I did sleep very well. The staff was excellent. So very friendly, helpful and attentive! They had a really good breakfast, which I enjoyed. I would definitely ..."
Reviewed on Oct 5, 2026
Sleep Inn & Suites Lancaster-Platteville
1600 S Madison Street Lancaster WI
Fully refundable
$95 nightly
$100 total
Oct 25 - Oct 26
Total with taxes and fees
9.4/10 Exceptional! (380 reviews)
"The staff was very friendly, easy to talk to. We enjoyed the breakfast and the pride the staff showed to provide the selection of food."
Reviewed on Sep 30, 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.
Find the Best Highland Vacation Packages
Highland Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 840 |
Max Temp Winter | 25ºF |
Max Temp Summer | 80ºF |
Top Sights | Beach at Black Hawk Lake Recreation Area, Spurgeon Vineyards & Winery and Blackhawk Lake Recreation Area |
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Frequently asked questions
How much does a Highland vacation package cost?
You can grab a vacation package to this top destination from $465 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?
December, January and February are great times to look for cheap Highland vacation packages. Opting to travel in quieter periods means you can typically find better prices on flights and accommodations.
How many days is enough for Highland?
Generally, a handful of days is enough to visit the top attractions during your Highland vacation. However, if you want to have time to relax or go on day trips, consider extending your itinerary.
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.
Does Expedia offer Book Now, Pay Later Highland vacation packages?
Secure your dream getaway to Highland with our Book Now, Pay Later vacations. No need to save like crazy or hold off until your next paycheck — we've joined forces with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no late payment fees or extra charges, it's easy to stay on budget and snap up bargains while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
