Highland Vacations from $742

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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.
Hilton Garden Inn Dubuque Downtown

Hilton Garden Inn Dubuque Downtown

3 out of 5
Price was $837, price is now $742 per person
$742
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Dubuque (DBQ)
8.8/10 Excellent! (1,000 reviews)
Not impressed with the desk staff, felt like we were a bother. Cleaning staff were very friendly and helpful.

Reviewed on Jul 15, 2025

Goldmoor Inn

Goldmoor Inn

4 out of 5
Price was $1,449, price is now $1,249 per person
$1,249
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Dubuque (DBQ)
8.8/10 Excellent! (597 reviews)
Beautiful Bed And Breakfast

Reviewed on Aug 3, 2025

Hotel Julien Dubuque

Hotel Julien Dubuque

3.5 out of 5
Downtown Dubuque
Price was $893, price is now $782 per person
$782
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Dubuque (DBQ)
9.2/10 Wonderful! (1,553 reviews)
The hotel is a beautiful place. Our room was amazing but could use an update on couches & chairs along with windows getting cleaned so you could see out better

Reviewed on Aug 20, 2025

Rivers Edge

Rivers Edge

2.5 out of 5
Price was $1,050, price is now $925 per person
$925
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Dubuque (DBQ)
10/10 Exceptional! (3 reviews)
it was so peaceful loved our stay

Reviewed on Apr 26, 2025

Chestnut Mountain Resort

Chestnut Mountain Resort

3 out of 5
Price was $870, price is now $769 per person
$769
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Dubuque (DBQ)
8.4/10 Very Good! (1,004 reviews)
Property was in much need of updating! Everything smells OLD. We stayed in the “premium” room. Aside from the nice view of the river, the room was very basic. Very small television that offered no channels at all. Luckily, I travel with my FireStick to help entertain my kid. The breakfast is overpriced for what you receive. Staff was friendly and polite!

Reviewed on Aug 19, 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

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

Highland: Driftless Fun Awaits

Highland: Driftless Fun Awaits

Highland
$233 nightly
The price is $243 total per night from Sep 1 to Sep 2
$243 total
Sep 1 - Sep 2
Total includes 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
$80 nightly
The price is $91 total per night from Sep 1 to Sep 2
$91 total
Sep 1 - Sep 2
Total includes taxes and fees
8/10 Very Good! (1,003 reviews)
"Not love Enough light for reading"

Reviewed on Aug 18, 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
$109 nightly
The price is $115 total per night from Aug 21 to Aug 22
$115 total
Aug 21 - Aug 22
Total includes taxes and fees
8.6/10 Excellent! (643 reviews)
"Decor was fabulous."

Reviewed on Aug 8, 2025

Deer Valley Lodge & Golf
See all 126 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.

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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 $742 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.