Highland Vacations from $448

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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.
Best Rest Inn & Suites

Best Rest Inn & Suites

2.5 out of 5
per person
Sep 18 - Sep 23
found 15 hours ago
Roundtrip non-stop flight included
New York (JFK) to Dubuque (DBQ)
7.6/10 Good! (28 reviews)
No Breakfast, no Coffe

Reviewed on May 18, 2025

SureStay Hotel by Best Western Manchester

SureStay Hotel by Best Western Manchester

2.5 out of 5
per person
Sep 18 - Sep 23
found 15 hours ago
Roundtrip non-stop flight included
New York (JFK) to Dubuque (DBQ)
7.4/10 Good! (417 reviews)
Great room configuration

Reviewed on May 29, 2025

Irish Cottage Inn & Suites

Irish Cottage Inn & Suites

3.5 out of 5
per person
Aug 14 - Aug 16
found 10 hours ago
Roundtrip flight included
Baltimore (BWI) to Dubuque (DBQ)
9.4/10 Exceptional! (1,123 reviews)
Great place to stay!

Reviewed on Jul 2, 2025

Grand Harbor Resort and Waterpark

Grand Harbor Resort and Waterpark

3.5 out of 5
per person
Aug 14 - Aug 16
found 10 hours ago
Roundtrip flight included
Baltimore (BWI) to Dubuque (DBQ)
7.8/10 Good! (1,015 reviews)
Great room facing river from 6th floor Very nice helpful staff. The check-in area is not a good representation of the hotel. It needs a remodel - it’s dark. I understand the “ship” theme but it isn’t appealing.

Reviewed on Jul 2, 2025

Chestnut Mountain Resort

Chestnut Mountain Resort

3 out of 5
per person
Aug 14 - Aug 16
found 10 hours ago
Roundtrip flight included
Baltimore (BWI) to Dubuque (DBQ)
8.4/10 Very Good! (1,001 reviews)
Nice hotel and Beautiful sunset

Reviewed on Jun 21, 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
$200 nightly
The price is $208 total per night from Jul 14 to Jul 15
$208 total
Jul 14 - Jul 15
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
Cheese Wedge Cabin Idyllic Farm
Cheese Wedge Cabin Idyllic Farm
Highland
$332 nightly
The price is $334 total per night from Jul 3 to Jul 4
$334 total
Jul 3 - Jul 4
Total includes taxes and fees
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
$80 nightly
The price is $91 total per night from Jul 3 to Jul 4
$91 total
Jul 3 - Jul 4
Total includes taxes and fees
8/10 Very Good! (1,003 reviews)
"Amazing place with great history and a full size airplane in the friars! What a story of WI ingenuity!"

Reviewed on Jun 30, 2025

Don Q Inn
See all 119 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 $448 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.