Highland Vacations from $362

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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

Baymont by Wyndham Dubuque

2.5 out of 5
Price was $394, price is now $362 per person
$362
per person
Nov 22 - Nov 25
found 14 hours ago
Roundtrip flight included
Chicago (CHI) to Dubuque (DBQ)
6.4/10 (1,008 reviews)
Breakfast was without a protein option.

Reviewed on Oct 11, 2025

Cobblestone Inn & Suites – Manchester

Cobblestone Inn & Suites – Manchester

3.5 out of 5
Price was $454, price is now $397 per person
$397
per person
Nov 22 - Nov 25
found 14 hours ago
Roundtrip flight included
Chicago (CHI) to Dubuque (DBQ)
9/10 Wonderful! (306 reviews)
The hotel was easy to find off and on. Room was clean and staff were friendly.

Reviewed on Oct 22, 2025

Hotel Julien Dubuque

Hotel Julien Dubuque

3.5 out of 5
Downtown Dubuque
Price was $523, price is now $464 per person
$464
per person
Nov 22 - Nov 25
found 14 hours ago
Roundtrip flight included
Chicago (CHI) to Dubuque (DBQ)
9.2/10 Wonderful! (1,650 reviews)
No window in our room? Is that even legal?

Reviewed on Oct 22, 2025

Chestnut Mountain Resort

Chestnut Mountain Resort

3 out of 5
Price was $489, price is now $434 per person
$434
per person
Nov 22 - Nov 25
found 14 hours ago
Roundtrip flight included
Chicago (CHI) to Dubuque (DBQ)
8.4/10 Very Good! (1,012 reviews)
We had a nice stay for the weekend with friends. The property could use a refresh with some updating. The outdoor patio area with views were beautiful.

Reviewed on Oct 22, 2025

Hotel Galena

Hotel Galena

2 out of 5
Price was $583, price is now $543 per person
$543
per person
Nov 22 - Nov 25
found 14 hours ago
Roundtrip flight included
Chicago (CHI) to Dubuque (DBQ)
9.6/10 Exceptional! (216 reviews)
Very personable and attentive. The hotel was clean and updated. We really enjoyed our stay there and will be staying again.

Reviewed on Oct 14, 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
$244 nightly
The price is $254 total per night from Nov 18 to Nov 19
$254 total
Nov 18 - Nov 19
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
$69 nightly
The price is $79 total per night from Nov 23 to Nov 24
$79 total
Nov 23 - Nov 24
Total with taxes and fees
8/10 Very Good! (1,014 reviews)
Very kitschy hotel with themed rooms. My partner and I went for our anniversary. He.loves planes, so the plane on the premises was great.

Reviewed on Oct 18, 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 Nov 9 to Nov 10
$64 total
Nov 9 - Nov 10
Total with taxes and fees
8.4/10 Very Good! (263 reviews)
We have been staying here every time we travel to this area for the past 4yrs. It is priced right, close to where our final destination is, and easy to access off the main road.

Reviewed on Oct 18, 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.

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 $362 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.