Highland Vacations from $507

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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.
Grant Hills Motel

Grant Hills Motel

2.5 out of 5
Price was $545, price is now $507 per person
$507
per person
Jul 30 - Aug 4
found 7 hours ago
Roundtrip non-stop flight included
New York (NYC) to Dubuque (DBQ)
8.2/10 Very Good! (225 reviews)
Charming motel outside of town. Very helpful staff.

Reviewed on May 31, 2026

Chestnut Mountain Resort

Chestnut Mountain Resort

3 out of 5
Price was $704, price is now $576 per person
$576
per person
Jul 30 - Aug 4
found 7 hours ago
Roundtrip non-stop flight included
New York (NYC) to Dubuque (DBQ)
8.6/10 Excellent! (1,005 reviews)
Fue una experiencia muy bonita todo en un solo lugar cómodo tranquilo con mucha naturaleza y ideal para pasarse en familia muy recomendable

Reviewed on May 26, 2026

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Discover the most popular places to visit in Highland

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.

Beach at Black Hawk Lake Recreation Area

Blackhawk Lake Recreation Area

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.

Blackhawk Lake Recreation Area

Spurgeon Vineyards & Winery

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.

Spurgeon Vineyards & Winery

Highland Hotel Deals

Cheese Wedge Cabin Idyllic Farm

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

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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
$90 nightly
The price is $102 total per night from Jun 7 to Jun 8
$102 total
Jun 7 - Jun 8
Total with taxes and fees
8/10 Very Good! (1,000 reviews)
"It may not be fancy or state of the art but we had a wonderful stay! The room was comfortable and clean. We didnt use the in room hot tub but the pool and jacuzzi were perfect as well. Very short drive from House on a rock."

Reviewed on Jun 2, 2026

Don Q Inn
Dodgeville inn and suites

Dodgeville inn and suites

2.5 out of 5
1308 n johns st Dodgeville WI
Fully refundableReserve now, pay when you stay
$58 nightly
The price is $66 total per night from Jun 8 to Jun 9
$66 total
Jun 8 - Jun 9
Total with taxes and fees
7.2/10 Good! (25 reviews)
"The first room smelled like cat piss. Wouldn’t give us our money back. Said we could have another room but if we used the tub we would be charged 60.00 extra dollars. We will never use or recommend the place to anyone again !!!"

Reviewed on Jun 1, 2026

Dodgeville inn and suites
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.

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 $507 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.