Highland Vacations from $501
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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.
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.
Highland Hotel Deals
Cheese Wedge Cabin Idyllic Farm
Highland WI
10/10 Exceptional! (1 review)
"If you are looking for a unconventional place to unplug and unwind, the Cheese Wedge Cabin is a charming getway. Etienne is a lovely host who made us feel welcome and comfortable on her farm. We got up close and personal with the sheep, chickens, and Phoenix the sheepdog (who is the gentlest giant ..."
Reviewed on Jul 28, 2025
Don Q Inn
3658 State Road 23 Dodgeville WI
Fully refundableReserve now, pay when you stay
$90 nightly
$102 total
Sep 7 - Sep 8
Total with taxes and fees
8/10 Very Good! (1,010 reviews)
"Stayed in the igloo room. Room could use some deep cleaning. The whirlpool tub was actually very clean though. Breakfast was pretty good. All in all a fun experience"
Reviewed on Aug 23, 2026
Sleep Inn & Suites Lancaster-Platteville
1600 S Madison Street Lancaster WI
Fully refundable
$94 nightly
$99 total
Sep 13 - Sep 14
Total with taxes and fees
9.4/10 Exceptional! (358 reviews)
"Excellent stay!! Clean room good Breskfast"
Reviewed on Aug 21, 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 $501 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.
