Highland Vacations from $833

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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.
SureStay Hotel by Best Western Manchester

SureStay Hotel by Best Western Manchester

2.5 out of 5
Price was $888, price is now $833 per person
$833
per person
Dec 28 - Dec 31
found 13 hours ago
Roundtrip flight included
Albany (ALB) to Dubuque (DBQ)
14.8/10 Exceptional! (450 reviews)
I wish they would have had wheat bread for toast.

Reviewed on Oct 12, 2025

Hilton Garden Inn Dubuque Downtown

Hilton Garden Inn Dubuque Downtown

3 out of 5
Price was $1,001, price is now $930 per person
$930
per person
Dec 28 - Dec 31
found 13 hours ago
Roundtrip flight included
Albany (ALB) to Dubuque (DBQ)
17.6/10 Exceptional! (1,001 reviews)
Breakfast not included, safe environment and clean

Reviewed on Nov 18, 2025

Hotel Galena

Hotel Galena

2 out of 5
Price was $1,216, price is now $1,133 per person
$1,133
per person
Dec 28 - Dec 31
found 13 hours ago
Roundtrip flight included
Albany (ALB) to Dubuque (DBQ)
19.2/10 Exceptional! (225 reviews)
This hotel is a little gem - great room (#2) in a historic building with great facilities and very comfortable bed. Great value and within easy walking distance of downtown Galena

Reviewed on Nov 23, 2025

Stoney Creek Inn Galena

Stoney Creek Inn Galena

2 out of 5
Price was $909, price is now $860 per person
$860
per person
Dec 28 - Dec 31
found 13 hours ago
Roundtrip flight included
Albany (ALB) to Dubuque (DBQ)
18.8/10 Exceptional! (1,276 reviews)
very quiet and the staff was friendly.

Reviewed on Nov 20, 2025

Cobblestone Inn & Suites – Manchester

Cobblestone Inn & Suites – Manchester

3.5 out of 5
Price was $909, price is now $870 per person
$870
per person
Dec 28 - Dec 31
found 13 hours ago
Roundtrip flight included
Albany (ALB) to Dubuque (DBQ)
18/10 Exceptional! (316 reviews)
The hotel room was clean and comfortable. The breakfast was hot and delicious. But we had a terrible time checking in. The hotel had not received our reservation from Expedia. It took an hour with online support and finally the Expedia supervisor calling the hotel to get the situation resolved. Then everything was fine. There is no elevator to the second floor.

Reviewed on Nov 18, 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 WI
$308 nightly
The price is $322 total per night from Nov 25 to Nov 26
$322 total
Nov 25 - Nov 26
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
$67 nightly
The price is $77 total per night from Nov 25 to Nov 26
$77 total
Nov 25 - Nov 26
Total with taxes and fees
8/10 Very Good! (1,000 reviews)
Vintage plane parked in front; you can go inside of it.

Reviewed on Nov 15, 2025

Don Q Inn
Deer Valley Lodge & Golf

Deer Valley Lodge & Golf

2.5 out of 5
401 West Industrial Drive Barneveld WI
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $94 total per night from Nov 25 to Nov 26
$94 total
Nov 25 - Nov 26
Total with taxes and fees
8.8/10 Excellent! (673 reviews)
friendly staff nice room and comfortable bed. breakfast area was clean and refilled often.

Reviewed on Nov 19, 2025

Deer Valley Lodge & Golf
See all 120 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 $833 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.