Highland Vacations from $321

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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.
Super 8 by Wyndham Dyersville near Field of Dreams

Super 8 by Wyndham Dyersville near Field of Dreams

2.5 out of 5
Price was $360, price is now $321 per person
$321
per person
Nov 10 - Nov 13
found 16 hours ago
Roundtrip flight included
Chicago (CHI) to Dubuque (DBQ)
8.4/10 Very Good! (691 reviews)
Clean rooms, great service. Staff was great.

Reviewed on Oct 4, 2025

Hotel Julien Dubuque

Hotel Julien Dubuque

3.5 out of 5
Downtown Dubuque
Price was $467, price is now $398 per person
$398
per person
Nov 10 - Nov 13
found 16 hours ago
Roundtrip flight included
Chicago (CHI) to Dubuque (DBQ)
9.2/10 Wonderful! (1,612 reviews)
Such a beautiful hotel. Always a pleasure staying.

Reviewed on Oct 9, 2025

Rivers Edge

Rivers Edge

2.5 out of 5
Price was $620, price is now $530 per person
$530
per person
Nov 10 - Nov 13
found 16 hours ago
Roundtrip flight included
Chicago (CHI) to Dubuque (DBQ)
10/10 Exceptional! (3 reviews)
it was so peaceful loved our stay

Reviewed on Apr 26, 2025

Hilton Garden Inn Dubuque Downtown

Hilton Garden Inn Dubuque Downtown

3 out of 5
Price was $450, price is now $386 per person
$386
per person
Nov 10 - Nov 13
found 16 hours ago
Roundtrip flight included
Chicago (CHI) to Dubuque (DBQ)
8.8/10 Excellent! (1,002 reviews)
Nice spot for a quick weekend trip. Construction on a new building next door which took up much of the parking lot. However, staff was helpful and offered a shuttle to the casino. Strongly recommend Catfish Charlie’s for dinner nearby.

Reviewed on Oct 5, 2025

Baymont by Wyndham Dubuque

Baymont by Wyndham Dubuque

2.5 out of 5
Price was $363, price is now $323 per person
$323
per person
Nov 10 - Nov 13
found 16 hours ago
Roundtrip flight included
Chicago (CHI) to Dubuque (DBQ)
6.4/10 (1,002 reviews)
Overall teh stay was a good experience. The reason I gave 4 stars rather than 5 is the breakfast was disappointing. No protein options at all. Had waffles, biscuits and sausage gravy which were both good as well as cold cereal and breads. No eggs, meat yogurt or fruit was available on either day of our 2 day stay.

Reviewed on Sep 8, 2025

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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

5/5(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.

Blackhawk Lake Recreation Area

Spurgeon Vineyards & Winery

4.5/5(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.

Spurgeon Vineyards & Winery

Highland Hotel Deals

Highland: Driftless Fun Awaits

Highland: Driftless Fun Awaits

Highland
$254 nightly
The price is $265 total per night from Oct 15 to Oct 16
$265 total
Oct 15 - Oct 16
Total with taxes and fees
10/10 Exceptional! (1 review)
"Great property. Had everything we needed. Highly recommend."

Reviewed on May 27, 2025

Highland: Driftless Fun Awaits
Don Q Inn

Don Q Inn

2.5 out of 5
3658 State Road 23, Dodgeville, WI
Fully refundableReserve now, pay when you stay
$68 nightly
The price is $78 total per night from Nov 10 to Nov 11
$78 total
Nov 10 - Nov 11
Total with taxes and fees
8/10 Very Good! (1,005 reviews)
"Initially we were disappointed with our room….when we made it known the manager quickly handled it…with an upgrade. He was very friendly and concerned with the guests happiness."

Reviewed on Oct 4, 2025

Don Q Inn
Quality Inn & Suites Belmont Route 151

Quality Inn & Suites Belmont Route 151

2.5 out of 5
103 W Mound View Avenue, Belmont, WI
Fully refundableReserve now, pay when you stay
$59 nightly
The price is $64 total per night from Oct 26 to Oct 27
$64 total
Oct 26 - Oct 27
Total with taxes and fees
8.4/10 Very Good! (255 reviews)
"My dog and I stayed 5 nights here as we explored 5 different Wisconsin State Parks within an hour radius of the hotel. Enjoyed the salt water pool, hot breakfast daily, and being able to go to the Crazy Cow Saloon for dinner and not leave the hotel was really nice! Staff was friendly, and there is ..."

Reviewed on Oct 3, 2025

Quality Inn & Suites Belmont Route 151
See all 123 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.

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 $321 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.